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This lovely waterfront home is tucked away on a quiet cul-de-sac in desirable Prospect Bay. Thoughtfully designed and built by the original owners, this home offers approximately 2796' of well-planned living space providing 4 bedrooms and 2.5 baths. The open-concept floor plan is enhanced by distinctive architectural details and abundant natural light. A bright kitchen opens to the family room with fireplace—perfect for everyday living and entertaining. The spacious living room features a vaulted ceiling with skylights and opens to a loft area above. The main-level primary bedroom offers water views, a large walk-in closet, and a full bath with soaking tub and walk-in shower. Upstairs, you’ll find three additional bedrooms plus a dedicated office space. Enjoy outdoor living on the wrap-around deck, accessible from the living room, kitchen, and primary bedroom. Additional features include an oversized two-car garage and private pier on a tranquil waterfront setting. Roof is 2 years old and carpet is new. Home is being sold As-Is. Buyer to verify water depth. Prospect Bay amenities include Golf, Pool, Boat Ramp, Tennis Ct, Club House with restaurant/bar/grill plus more.

222 Piney Point Lndg, Grasonville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,650,000

Experience waterfront living at its absolute finest in this breathtaking, fully renovated Chester River estate, where shimmering water views unfold from nearly every window and the lifestyle is nothing short of extraordinary. With 125 feet of pristine shoreline and sweeping panoramic river vistas, this remarkable property is equally suited as a luxurious primary residence or an unforgettable vacation retreat. The recent addition expanded the main level footprint and added the second story over the main part of the home. The welcoming family room impresses with soaring vaulted ceilings and a cozy fireplace framed by a refined panel-molding accent wall, creating an inviting yet elegant gathering space. Just beyond, the sun-drenched main-level sunroom offers vaulted ceilings, ceramic tile flooring, a ceiling fan, and dramatic picture windows that frame the water like living art. At the heart of the home is a magazine-worthy kitchen renovation featuring custom cabinetry, granite countertops, pull-out drawers, gas cooking, and upgraded GE appliances, all anchored by a statement center island with pendant lighting. A stylish dry bar with display cabinetry adds a sophisticated touch, while the open-concept design flows effortlessly into the dining and family rooms. Perfectly positioned to capture the ever-changing river scenery, hardwood floors and recessed lighting grace the common areas, while walls of windows and sliding glass doors invite the outdoors in and open directly to the expansive waterfront deck. The main-level primary suite is a serene sanctuary with tranquil water views, a walk-in closet with custom organization, and a spa-inspired ensuite bath highlighted by a large tiled stall shower. Two additional main-level bedrooms, each appointed with ceiling fans and plush carpeting, are thoughtfully served by a beautifully finished hall bath, providing comfort and privacy for family and guests alike. Upstairs a charming loft creates a peaceful reading nook or relaxation space. Two additional bedrooms with plush carpeting and ceiling fans share access to an upstairs hall bath, while a cozy flex room, ideal for a home office, features carpeting and a delightful round window. Adding to the home’s versatility is a private second upper-level suite located above the two-car garage, offering an expansive bedroom with an architecturally striking half-wall separating a sitting or office area, along with a spacious en-suite bath, perfect for guests or multi-generational living. Outdoors, the property truly becomes unforgettable. 125 feet of unobstructed Chester River frontage provides direct access to the water, complemented by a deep-water dock with a boat lift and two jet ski lifts, all conveyed as-is. An enormous IPE wood deck creates an exceptional setting for entertaining, complete with a hot tub and a covered outdoor kitchen featuring a bar, grill, sink, ice maker, and even a full bath, delivering a true resort-style experience at home. A graceful circular driveway enhances both curb appeal and convenience, offering ample parking for guests. Recent improvements include a new roof and siding (2023), a replaced well and pump (2017), and the added luxury of a water softener and whole-house reverse osmosis system. This extraordinary waterfront residence seamlessly blends refined renovations, exceptional indoor and outdoor amenities, and an unparalleled riverfront setting, presenting a rare opportunity to own a true Chester River masterpiece.

6 Beds ⋅ 5 Baths

Experience waterfront living at its absolute finest in this breathtaking, fully renovated Chester River estate, where shimmering water views unfold from nearly every window and the lifestyle is nothing short of extraordinary. With 125 feet of pristine shoreline and sweeping panoramic river vistas, this remarkable property is equally suited as a luxurious primary residence or an unforgettable vacation retreat. The recent addition expanded the main level footprint and added the second story over the main part of the home. The welcoming family room impresses with soaring vaulted ceilings and a cozy fireplace framed by a refined panel-molding accent wall, creating an inviting yet elegant gathering space. Just beyond, the sun-drenched main-level sunroom offers vaulted ceilings, ceramic tile flooring, a ceiling fan, and dramatic picture windows that frame the water like living art. At the heart of the home is a magazine-worthy kitchen renovation featuring custom cabinetry, granite countertops, pull-out drawers, gas cooking, and upgraded GE appliances, all anchored by a statement center island with pendant lighting. A stylish dry bar with display cabinetry adds a sophisticated touch, while the open-concept design flows effortlessly into the dining and family rooms. Perfectly positioned to capture the ever-changing river scenery, hardwood floors and recessed lighting grace the common areas, while walls of windows and sliding glass doors invite the outdoors in and open directly to the expansive waterfront deck. The main-level primary suite is a serene sanctuary with tranquil water views, a walk-in closet with custom organization, and a spa-inspired ensuite bath highlighted by a large tiled stall shower. Two additional main-level bedrooms, each appointed with ceiling fans and plush carpeting, are thoughtfully served by a beautifully finished hall bath, providing comfort and privacy for family and guests alike. Upstairs a charming loft creates a peaceful reading nook or relaxation space. Two additional bedrooms with plush carpeting and ceiling fans share access to an upstairs hall bath, while a cozy flex room, ideal for a home office, features carpeting and a delightful round window. Adding to the home’s versatility is a private second upper-level suite located above the two-car garage, offering an expansive bedroom with an architecturally striking half-wall separating a sitting or office area, along with a spacious en-suite bath, perfect for guests or multi-generational living. Outdoors, the property truly becomes unforgettable. 125 feet of unobstructed Chester River frontage provides direct access to the water, complemented by a deep-water dock with a boat lift and two jet ski lifts, all conveyed as-is. An enormous IPE wood deck creates an exceptional setting for entertaining, complete with a hot tub and a covered outdoor kitchen featuring a bar, grill, sink, ice maker, and even a full bath, delivering a true resort-style experience at home. A graceful circular driveway enhances both curb appeal and convenience, offering ample parking for guests. Recent improvements include a new roof and siding (2023), a replaced well and pump (2017), and the added luxury of a water softener and whole-house reverse osmosis system. This extraordinary waterfront residence seamlessly blends refined renovations, exceptional indoor and outdoor amenities, and an unparalleled riverfront setting, presenting a rare opportunity to own a true Chester River masterpiece.

1017 Long Point Rd, Grasonville

Listing courtesy of Northrop Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$1,600,000

Welcome to 1026 Long Point Road, Grasonville, MD — a waterfront retreat on the Chester River with sunrise out back and sunset out front. Completely renovated inside and out in 2017, this 6-bedroom, 5.5-bath home combines timeless coastal charm with modern updates, offering water views from every room. The renovation included a new roof, siding, windows, HVAC, hardwood floors, carpet, doors, appliances, bulkhead, pier, boat lift, and decks — truly turn-key and ready for years of enjoyment. Designed for entertaining, the main level features expansive living and family rooms, a large dining area plus breakfast nook, and multiple sliders leading to the waterside deck with sleek cable railing. The spacious kitchen opens seamlessly to the deck—ideal for gatherings that flow from indoors to out. There are two bedrooms and 3 full bathrooms on the main level. A large laundry room and a versatile office (or additional bedroom) complete the first floor. Upstairs, two primary suites each offer en-suite baths and water views, separated by a comfortable sitting area. The main primary suite includes a private balcony overlooking the river. An additional guest bedroom upstairs with a half bath provides even more space for family or visitors. Outside, the private pier with an 8,000 lb. boat lift and 4–5 ft. MLW invites effortless boating, crabbing, and fishing right from your backyard. A shed provides extra storage for gear and equipment. Located near the end of the Long Point peninsula, where homes rarely come available, this property offers privacy and proximity to everything you love about the Eastern Shore—walk or bike the Cross Island Trail, easily boat to Kent Narrows, Rock Hall, Chestertown, and St. Michaels, and enjoy quick access to Route 50/301, shopping, restaurants, and nightlife. Whether you’re looking for a primary residence, weekend escape, or vacation rental investment, 1026 Long Point Road delivers the perfect blend of comfort, convenience, and Chesapeake charm.

6 Beds ⋅ 6 Baths

Welcome to 1026 Long Point Road, Grasonville, MD — a waterfront retreat on the Chester River with sunrise out back and sunset out front. Completely renovated inside and out in 2017, this 6-bedroom, 5.5-bath home combines timeless coastal charm with modern updates, offering water views from every room. The renovation included a new roof, siding, windows, HVAC, hardwood floors, carpet, doors, appliances, bulkhead, pier, boat lift, and decks — truly turn-key and ready for years of enjoyment. Designed for entertaining, the main level features expansive living and family rooms, a large dining area plus breakfast nook, and multiple sliders leading to the waterside deck with sleek cable railing. The spacious kitchen opens seamlessly to the deck—ideal for gatherings that flow from indoors to out. There are two bedrooms and 3 full bathrooms on the main level. A large laundry room and a versatile office (or additional bedroom) complete the first floor. Upstairs, two primary suites each offer en-suite baths and water views, separated by a comfortable sitting area. The main primary suite includes a private balcony overlooking the river. An additional guest bedroom upstairs with a half bath provides even more space for family or visitors. Outside, the private pier with an 8,000 lb. boat lift and 4–5 ft. MLW invites effortless boating, crabbing, and fishing right from your backyard. A shed provides extra storage for gear and equipment. Located near the end of the Long Point peninsula, where homes rarely come available, this property offers privacy and proximity to everything you love about the Eastern Shore—walk or bike the Cross Island Trail, easily boat to Kent Narrows, Rock Hall, Chestertown, and St. Michaels, and enjoy quick access to Route 50/301, shopping, restaurants, and nightlife. Whether you’re looking for a primary residence, weekend escape, or vacation rental investment, 1026 Long Point Road delivers the perfect blend of comfort, convenience, and Chesapeake charm.

1026 Long Point Rd, Grasonville

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Engel & Volkers Annapolis.

$1,450,000

HIGHEST AND BEST DUE SUNDAY 10/19 6PM----Welcome to 16 Fairway Island, a 5,100 sq. ft. coastal-inspired estate designed for both everyday luxury and effortless entertaining. With a main-level primary suite, spacious office, and four oversized bedrooms upstairs, this home offers the perfect balance of comfort, style, and functionality. Step inside to soaring spaces wrapped in fresh paint, new luxury vinyl plank flooring , and upgraded lighting that bring a crisp, modern feel. The chef’s kitchen features a new cooktop, two dishwashers, a wine fridge, and professionally refinished cabinets — ideal for preparing family meals or hosting on a grand scale. A generous family room anchors the main level, while formal and casual dining spaces provide versatility for gatherings. The main-level primary suite is a private retreat, complete with spacious layout and spa-like finishes. Upstairs, four large bedrooms offer room for family, guests, or flexible use. A dedicated main-level office ensures work-from-home convenience without sacrificing style. Outside, enjoy your own private resort: a saltwater pool with recently upgraded motorized cover, outdoor shower, built-in umbrella, gas hookup, hot tub, built in fire pit, and a newly fenced yard framed by lush landscaping. And as a bonus — the property includes a pool house with a wood-burning fireplace, mini-split system, and water hookup, creating an additional entertaining space for summer pool parties or cozy fall evenings. Practical features include a 3-car garage with workbench and second-level storage, laundry located both upstairs and downstairs, interior crawlspace access, propane service, and annual HVAC maintenance for peace of mind. Located in the sought after golf course community of Prospect Bay, this award winning neighborhood offers the best of both worlds-- a premier 18 hole golf course and access to the Chesapeake Bay. Perfect for golf enthusiasts but it's not just about golf...residents enjoy full club amenities including fine and casual dining, tennis, pickleball, a marina, and a vibrant social calendar Prospect Bay combines resort-style amenities with an unbeatable Eastern Shore location This isn’t just a home — it’s lifestyle on Maryland’s Eastern Shore. https://unbranded.youriguide.com/1l8pu_16_fairway_island_grasonville_md/ **3DTour**

HIGHEST AND BEST DUE SUNDAY 10/19 6PM----Welcome to 16 Fairway Island, a 5,100 sq. ft. coastal-inspired estate designed for both everyday luxury and effortless entertaining. With a main-level primary suite, spacious office, and four oversized bedrooms upstairs, this home offers the perfect balance of comfort, style, and functionality. Step inside to soaring spaces wrapped in fresh paint, new luxury vinyl plank flooring , and upgraded lighting that bring a crisp, modern feel. The chef’s kitchen features a new cooktop, two dishwashers, a wine fridge, and professionally refinished cabinets — ideal for preparing family meals or hosting on a grand scale. A generous family room anchors the main level, while formal and casual dining spaces provide versatility for gatherings. The main-level primary suite is a private retreat, complete with spacious layout and spa-like finishes. Upstairs, four large bedrooms offer room for family, guests, or flexible use. A dedicated main-level office ensures work-from-home convenience without sacrificing style. Outside, enjoy your own private resort: a saltwater pool with recently upgraded motorized cover, outdoor shower, built-in umbrella, gas hookup, hot tub, built in fire pit, and a newly fenced yard framed by lush landscaping. And as a bonus — the property includes a pool house with a wood-burning fireplace, mini-split system, and water hookup, creating an additional entertaining space for summer pool parties or cozy fall evenings. Practical features include a 3-car garage with workbench and second-level storage, laundry located both upstairs and downstairs, interior crawlspace access, propane service, and annual HVAC maintenance for peace of mind. Located in the sought after golf course community of Prospect Bay, this award winning neighborhood offers the best of both worlds-- a premier 18 hole golf course and access to the Chesapeake Bay. Perfect for golf enthusiasts but it's not just about golf...residents enjoy full club amenities including fine and casual dining, tennis, pickleball, a marina, and a vibrant social calendar Prospect Bay combines resort-style amenities with an unbeatable Eastern Shore location This isn’t just a home — it’s lifestyle on Maryland’s Eastern Shore. https://unbranded.youriguide.com/1l8pu_16_fairway_island_grasonville_md/ **3DTour**

16 Fairway Is, Grasonville

Listing courtesy of Douglas Realty LLC. Contact:

Experience elevated waterfront living in one of Kent Narrows' most desirable marina communities. Perfectly positioned as an end-unit in prestigious Wells Cove Townhomes & Marina, this extensively renovated four-level residence captures sweeping Chesapeake Bay and marina views while offering the rare combination of refined finishes, deep-water boating, and a true lock-and-leave lifestyle. Ready for immediate occupancy, this is the turnkey waterfront home you've been waiting for. Spanning approximately 3,500 square feet, the thoughtfully designed floor plan features four bedrooms, four full baths, one half bath, and a private elevator servicing all four levels. Crafted to satisfy even the most discerning buyer, the home reflects an uncompromising commitment to quality, comfort, and timeless design. Rich hardwood flooring, custom millwork, designer lighting, soaring 9-foot ceilings, abundant natural light, and beautifully renovated interiors create an atmosphere that is both sophisticated and inviting. At the heart of the home is a stunning chef's kitchen, completely redesigned in 2019 with custom cabinetry, premium appliances, stone countertops, an oversized center island, and exceptional workspace. Multiple living and entertaining areas, two spacious owner suites, a loft, and a generous recreation room with a wet bar provide remarkable flexibility for family and guests alike. Four private covered waterfront decks seamlessly extend the living space outdoors, creating the perfect setting to enjoy morning coffee, watch boats glide through the marina, or unwind with spectacular Chesapeake Bay sunsets. From nearly every level, the ever-changing waterfront views become part of everyday life. For boating enthusiasts, the deeded deep-water boat slip is one of the marina's most desirable, offering approximately 4 feet of mean low water and the ability to accommodate a substantial vessel. Ideally positioned for convenient access to the Chesapeake Bay, it provides an exceptional home port for everything from an afternoon cruise to a weekend on the water. An oversized two-car garage offers generous storage for vehicles, bicycles, paddleboards, fishing gear, and all the essentials for an active waterfront lifestyle. Located in the heart of Kent Narrows, you're just moments from waterfront restaurants, marinas, boutique shopping, the Cross Island Trail, golf, and Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches. Beautifully renovated, impeccably maintained, and completely turnkey, this extraordinary residence presents a rare opportunity to own one of Wells Cove's premier waterfront homes. Simply arrive, settle in, and begin enjoying the Chesapeake Bay lifestyle from day one.

$1,391,000

4 Beds ⋅ 5 Baths

Experience elevated waterfront living in one of Kent Narrows' most desirable marina communities. Perfectly positioned as an end-unit in prestigious Wells Cove Townhomes & Marina, this extensively renovated four-level residence captures sweeping Chesapeake Bay and marina views while offering the rare combination of refined finishes, deep-water boating, and a true lock-and-leave lifestyle. Ready for immediate occupancy, this is the turnkey waterfront home you've been waiting for. Spanning approximately 3,500 square feet, the thoughtfully designed floor plan features four bedrooms, four full baths, one half bath, and a private elevator servicing all four levels. Crafted to satisfy even the most discerning buyer, the home reflects an uncompromising commitment to quality, comfort, and timeless design. Rich hardwood flooring, custom millwork, designer lighting, soaring 9-foot ceilings, abundant natural light, and beautifully renovated interiors create an atmosphere that is both sophisticated and inviting. At the heart of the home is a stunning chef's kitchen, completely redesigned in 2019 with custom cabinetry, premium appliances, stone countertops, an oversized center island, and exceptional workspace. Multiple living and entertaining areas, two spacious owner suites, a loft, and a generous recreation room with a wet bar provide remarkable flexibility for family and guests alike. Four private covered waterfront decks seamlessly extend the living space outdoors, creating the perfect setting to enjoy morning coffee, watch boats glide through the marina, or unwind with spectacular Chesapeake Bay sunsets. From nearly every level, the ever-changing waterfront views become part of everyday life. For boating enthusiasts, the deeded deep-water boat slip is one of the marina's most desirable, offering approximately 4 feet of mean low water and the ability to accommodate a substantial vessel. Ideally positioned for convenient access to the Chesapeake Bay, it provides an exceptional home port for everything from an afternoon cruise to a weekend on the water. An oversized two-car garage offers generous storage for vehicles, bicycles, paddleboards, fishing gear, and all the essentials for an active waterfront lifestyle. Located in the heart of Kent Narrows, you're just moments from waterfront restaurants, marinas, boutique shopping, the Cross Island Trail, golf, and Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches. Beautifully renovated, impeccably maintained, and completely turnkey, this extraordinary residence presents a rare opportunity to own one of Wells Cove's premier waterfront homes. Simply arrive, settle in, and begin enjoying the Chesapeake Bay lifestyle from day one.

314 Channel Marker Way, Grasonville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Keller Williams Realty Centre.

$1,350,000

Welcome to this beautifully updated waterfront-view home in Prospect Bay, the premier golf course community on the Eastern Shore! This home tastefully blends coastal charm with modern design and exceptional outdoor living. From the moment you arrive via the paved driveway to the two-car garage, you are greeted by serene water views from the front entrance and porches off the living room and sunroom. Inside, an open entryway with ample storage leads to a formal living room with masonry fireplace that flows seamlessly into a completely remodeled dining room featuring tasteful textured wallpaper, bead and board wall trim. On the opposite side of the entry, a spacious family room boasts a new electric fireplace with shiplap accent wall and quartz hearth. A stylish powder room with statement wallpaper and a new quartz countertop, along with hardwood floors throughout both levels, add to the home’s polished feel. The home offers easy interior access from the two-car garage, with a staircase tucked away down the same hallway that leads to a large room over the garage with dedicated heat pump. Perfect for use as a home office, extra bedroom, additional storage, or craft room. The upgraded kitchen shines with new countertops and backsplash, a remodeled island for added storage, and enhanced carpentry details, flowing into a bright sunroom with pool and water views ideal for an office or hobby space. Just beyond the kitchen, doors open to your private backyard oasis, complete with a deck featuring upgraded Trex materials, extensive hardscaping surrounding a large inground pool, a hot tub installed in 2022, and fresh landscaping framed by mature trees for ultimate privacy. A charming coastal-style guest house with high efficiency mini split units, sits steps from the pool, offering a kitchenette, living area, full bathroom, and bedroom for visitors or extended stays. Upstairs, the primary suite impresses with water views, a masonry fireplace, an expanded walk-in closet outfitted with a custom Elfa system, and a remodeled spa-like bathroom featuring a tiled shower with marble seat, soaking tub, dual vanities, and updated fixtures. Three additional bedrooms share a well-appointed guest bathroom. Recent major upgrades include a new roof and gutters (2024), attic plywood flooring for extra storage, encapsulated crawlspace (2023), three high-efficiency heat pumps (2023), freshly painted and caulked exterior, repaved and resealed driveway, updated garage including flooring, storage cabinets, work bench and door operators. The property also offers a whole-house generator, updated trim work throughout, and so much more, making this home truly move-in ready. Located within the exclusive Prospect Bay Community, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this water view property offers an unmatched lifestyle in one of Maryland's most prestigious communities.

Welcome to this beautifully updated waterfront-view home in Prospect Bay, the premier golf course community on the Eastern Shore! This home tastefully blends coastal charm with modern design and exceptional outdoor living. From the moment you arrive via the paved driveway to the two-car garage, you are greeted by serene water views from the front entrance and porches off the living room and sunroom. Inside, an open entryway with ample storage leads to a formal living room with masonry fireplace that flows seamlessly into a completely remodeled dining room featuring tasteful textured wallpaper, bead and board wall trim. On the opposite side of the entry, a spacious family room boasts a new electric fireplace with shiplap accent wall and quartz hearth. A stylish powder room with statement wallpaper and a new quartz countertop, along with hardwood floors throughout both levels, add to the home’s polished feel. The home offers easy interior access from the two-car garage, with a staircase tucked away down the same hallway that leads to a large room over the garage with dedicated heat pump. Perfect for use as a home office, extra bedroom, additional storage, or craft room. The upgraded kitchen shines with new countertops and backsplash, a remodeled island for added storage, and enhanced carpentry details, flowing into a bright sunroom with pool and water views ideal for an office or hobby space. Just beyond the kitchen, doors open to your private backyard oasis, complete with a deck featuring upgraded Trex materials, extensive hardscaping surrounding a large inground pool, a hot tub installed in 2022, and fresh landscaping framed by mature trees for ultimate privacy. A charming coastal-style guest house with high efficiency mini split units, sits steps from the pool, offering a kitchenette, living area, full bathroom, and bedroom for visitors or extended stays. Upstairs, the primary suite impresses with water views, a masonry fireplace, an expanded walk-in closet outfitted with a custom Elfa system, and a remodeled spa-like bathroom featuring a tiled shower with marble seat, soaking tub, dual vanities, and updated fixtures. Three additional bedrooms share a well-appointed guest bathroom. Recent major upgrades include a new roof and gutters (2024), attic plywood flooring for extra storage, encapsulated crawlspace (2023), three high-efficiency heat pumps (2023), freshly painted and caulked exterior, repaved and resealed driveway, updated garage including flooring, storage cabinets, work bench and door operators. The property also offers a whole-house generator, updated trim work throughout, and so much more, making this home truly move-in ready. Located within the exclusive Prospect Bay Community, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this water view property offers an unmatched lifestyle in one of Maryland's most prestigious communities.

228 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: RE/MAX Executive.

$1,300,000

Expansive views stretch along Jackson Creek to the Chester River, creating a waterfront setting that is truly exceptional. For anyone who loves life on the water, this property offers a rare opportunity, complete with a sandy beach and impressive waterfront frontage. The outdoor amenities are designed for both relaxation and recreation, including a pier with boat lift and electric, a beach house cabana, pool, pergola, hardscape, and plenty of space for poolside entertaining. Natural light fills the home from sunrise over the Chester River throughout the day as the sun moves west. The main house is in excellent condition and offers multiple living spaces, including three sitting areas, a breakfast room, and a formal dining room. Beautiful finishes include hardwood floors, cherry kitchen cabinetry, stainless steel appliances, and a beverage bar. A stone fireplace adds warmth and ambiance to the open living areas. The home features five bedrooms, three full baths, and one-half bath, with hardwood flooring throughout both levels. A first-floor bedroom with a full bath provides flexibility for guests or multigenerational living. The primary suite is ideally positioned on the waterside and includes a private balcony. An indoor porch, outdoor porches, and a game room make this home especially well-suited for entertaining. Surrounded by mature trees, the property also offers a spacious yard with fencing already in place for children and pets.

Expansive views stretch along Jackson Creek to the Chester River, creating a waterfront setting that is truly exceptional. For anyone who loves life on the water, this property offers a rare opportunity, complete with a sandy beach and impressive waterfront frontage. The outdoor amenities are designed for both relaxation and recreation, including a pier with boat lift and electric, a beach house cabana, pool, pergola, hardscape, and plenty of space for poolside entertaining. Natural light fills the home from sunrise over the Chester River throughout the day as the sun moves west. The main house is in excellent condition and offers multiple living spaces, including three sitting areas, a breakfast room, and a formal dining room. Beautiful finishes include hardwood floors, cherry kitchen cabinetry, stainless steel appliances, and a beverage bar. A stone fireplace adds warmth and ambiance to the open living areas. The home features five bedrooms, three full baths, and one-half bath, with hardwood flooring throughout both levels. A first-floor bedroom with a full bath provides flexibility for guests or multigenerational living. The primary suite is ideally positioned on the waterside and includes a private balcony. An indoor porch, outdoor porches, and a game room make this home especially well-suited for entertaining. Surrounded by mature trees, the property also offers a spacious yard with fencing already in place for children and pets.

110 Perrys Rd, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$1,240,000

Tucked behind mature trees on a private 1.02-acre lot with a creek glimpse from the home, this 4,000+ sq ft coastal home sits inside Prospect Bay, Grasonville's premier golf communities — and it lives every bit as well as it looks. The kitchen is the showpiece. Built for the cook who loves to entertain, it's outfitted with high-end commercial-grade appliances, including a commercial range, anchored by a center island and a walk-in pantry — ready for everything from weeknight dinners to holidays with a full house. Rich hardwood floors run throughout, framed by 9'+ ceilings, crown molding, and recessed lighting that give every room a warm, finished feel. There's room to spread out and room to unwind. A spacious living room addition and a screened-in porch extend the everyday living space, while out back the deck, fenced in-ground saltwater pool, and dedicated pool house turn the private yard into a true retreat. The primary suite is its own escape, with an attached bathroom that features double sinks and luxury shower, walk-in closet, and private deck access. Three bedrooms, 3.5 baths, a formal dining room, a dedicated office, and a side-entry two-car garage complete the floor plan — all behind a classic hardiplank exterior built to last. Then there's the lifestyle. Prospect Bay is a resort-style community wrapped around an 18-hole golf course, with access to a community pool, tennis and pickleball courts, and a clubhouse with casual and fine dining. A private community waterfront adds a marina, boat ramp, pier, and kayak launch with available storage. You're roughly ten minutes from the Bay Bridge, 25 minutes from Annapolis, Easton, and St. Michael's, and about an hour from Baltimore and D.C. Homes of this size rarely come available here. If you've been waiting for the right home on the Shore — this is it.

3 Beds ⋅ 3 Baths

Tucked behind mature trees on a private 1.02-acre lot with a creek glimpse from the home, this 4,000+ sq ft coastal home sits inside Prospect Bay, Grasonville's premier golf communities — and it lives every bit as well as it looks. The kitchen is the showpiece. Built for the cook who loves to entertain, it's outfitted with high-end commercial-grade appliances, including a commercial range, anchored by a center island and a walk-in pantry — ready for everything from weeknight dinners to holidays with a full house. Rich hardwood floors run throughout, framed by 9'+ ceilings, crown molding, and recessed lighting that give every room a warm, finished feel. There's room to spread out and room to unwind. A spacious living room addition and a screened-in porch extend the everyday living space, while out back the deck, fenced in-ground saltwater pool, and dedicated pool house turn the private yard into a true retreat. The primary suite is its own escape, with an attached bathroom that features double sinks and luxury shower, walk-in closet, and private deck access. Three bedrooms, 3.5 baths, a formal dining room, a dedicated office, and a side-entry two-car garage complete the floor plan — all behind a classic hardiplank exterior built to last. Then there's the lifestyle. Prospect Bay is a resort-style community wrapped around an 18-hole golf course, with access to a community pool, tennis and pickleball courts, and a clubhouse with casual and fine dining. A private community waterfront adds a marina, boat ramp, pier, and kayak launch with available storage. You're roughly ten minutes from the Bay Bridge, 25 minutes from Annapolis, Easton, and St. Michael's, and about an hour from Baltimore and D.C. Homes of this size rarely come available here. If you've been waiting for the right home on the Shore — this is it.

43 Greenwood Shls, Grasonville

Listing courtesy of Real Broker, LLC - Chester. Contact:

Finally, one of the highly sought-after “Big Six” Waterfront Townhomes is available—complete with an attached garage and deeded boat slip (M1-PB-11) in the protected North Marina. This exceptional property truly represents the best of Waterfront Living. Fully renovated just four years ago with top-of-the-line finishes and beautiful coastal design throughout. Features include ¾" luxury vinyl plank flooring, a bright designer kitchen with commercial-grade Thermador stainless steel appliances. At the center of the space is a stunning custom “River Table” island that serves as an unforgettable showpiece.. Floor-to-ceiling glass captures breathtaking Eastern Bay views and fills the home with natural light. Each level offers its own deck - perfect for entertaining or simply enjoying spectacular Water Views and sunsets just steps from your door. The first level offers a versatile bonus room ideal for a recreation room or additional primary suite, complete with a beautifully designed bath and modern fireplace. The open-concept kitchen, dining, and family room feature another fireplace (gas burning) and sweeping WATER VIEWS. The spacious primary suite offers incredible waterfront views ,vaulted ceiling, and nothing less than a magazine-worthy bath. Two additional guest rooms and a beautifully appointed hall bath complete the upper level. Even the garage is decorated "Retro Flair" including a kitchenette , extra storage, and still room for your car! This is the perfect get away or better yet, live here year around! It's the perfect one of a kind coastal retreat! Residents enjoy a beautiful clubhouse with party room, fitness center, and saltwater pool, along with tennis/pickleball courts and a basketball court. A scenic 1.5-mile waterfront path connects to the Cross Island Trail, a 38-mile award-winning trail linking beaches, parks, marinas, shops, restaurants, coffee spots, and ice cream shops. Just 7 minutes to Queenstown Harbor Golf and Prime Outlets, 20 minutes to Annapolis and Easton, and under an hour to Washington, DC and Baltimore. It’s not just a home—it’s a lifestyle. 🌅🏡

$1,200,000

Finally, one of the highly sought-after “Big Six” Waterfront Townhomes is available—complete with an attached garage and deeded boat slip (M1-PB-11) in the protected North Marina. This exceptional property truly represents the best of Waterfront Living. Fully renovated just four years ago with top-of-the-line finishes and beautiful coastal design throughout. Features include ¾" luxury vinyl plank flooring, a bright designer kitchen with commercial-grade Thermador stainless steel appliances. At the center of the space is a stunning custom “River Table” island that serves as an unforgettable showpiece.. Floor-to-ceiling glass captures breathtaking Eastern Bay views and fills the home with natural light. Each level offers its own deck - perfect for entertaining or simply enjoying spectacular Water Views and sunsets just steps from your door. The first level offers a versatile bonus room ideal for a recreation room or additional primary suite, complete with a beautifully designed bath and modern fireplace. The open-concept kitchen, dining, and family room feature another fireplace (gas burning) and sweeping WATER VIEWS. The spacious primary suite offers incredible waterfront views ,vaulted ceiling, and nothing less than a magazine-worthy bath. Two additional guest rooms and a beautifully appointed hall bath complete the upper level. Even the garage is decorated "Retro Flair" including a kitchenette , extra storage, and still room for your car! This is the perfect get away or better yet, live here year around! It's the perfect one of a kind coastal retreat! Residents enjoy a beautiful clubhouse with party room, fitness center, and saltwater pool, along with tennis/pickleball courts and a basketball court. A scenic 1.5-mile waterfront path connects to the Cross Island Trail, a 38-mile award-winning trail linking beaches, parks, marinas, shops, restaurants, coffee spots, and ice cream shops. Just 7 minutes to Queenstown Harbor Golf and Prime Outlets, 20 minutes to Annapolis and Easton, and under an hour to Washington, DC and Baltimore. It’s not just a home—it’s a lifestyle. 🌅🏡

1009 Oyster Cove Dr, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

Selling Office: Compass.

$1,160,000

Luxury Waterfront Living in a Gated Community Enjoy the best of waterfront living in this beautiful gated community, perfectly situated between the Chester River and Safe Harbor Marina. This stunning home offers breathtaking water views and an open, airy floor plan designed for both relaxing and entertaining. Inside, you'll find rich hardwood floors and spacious bedrooms, each featuring its own private bath and walk-in closet, offering comfort and privacy for everyone. The upgraded kitchen boasts high-end appliances, including a wine fridge, making it perfect for hosting. Step outside to the two rear decks, both equipped with remote-controlled screens, allowing you to enjoy the incredible views in comfort any time of day. Neighborhood has a living shore line and 3 piers. Additional highlights include: • Cozy fireplace for chilly evenings • Jetted soaking tub for spa-like relaxation • Condo association will be putting a fresh coat of paint on the exterior in May • New roof • 2 car garage • Tankless water heater * New washer and dryer • Located just 20 minutes from Annapolis This exceptional home combines luxury, comfort, and unbeatable waterfront scenery—truly a must-see! And so much more!

Luxury Waterfront Living in a Gated Community Enjoy the best of waterfront living in this beautiful gated community, perfectly situated between the Chester River and Safe Harbor Marina. This stunning home offers breathtaking water views and an open, airy floor plan designed for both relaxing and entertaining. Inside, you'll find rich hardwood floors and spacious bedrooms, each featuring its own private bath and walk-in closet, offering comfort and privacy for everyone. The upgraded kitchen boasts high-end appliances, including a wine fridge, making it perfect for hosting. Step outside to the two rear decks, both equipped with remote-controlled screens, allowing you to enjoy the incredible views in comfort any time of day. Neighborhood has a living shore line and 3 piers. Additional highlights include: • Cozy fireplace for chilly evenings • Jetted soaking tub for spa-like relaxation • Condo association will be putting a fresh coat of paint on the exterior in May • New roof • 2 car garage • Tankless water heater * New washer and dryer • Located just 20 minutes from Annapolis This exceptional home combines luxury, comfort, and unbeatable waterfront scenery—truly a must-see! And so much more!

430 Narrows Pointe Dr, Grasonville

Listing courtesy of RE/MAX United Real Estate. Contact:

Selling Office: RE/MAX Leading Edge.

$1,110,000

MAJOR PRICE IMPROVEMENT! Just in time to enjoy your Prospect Bay waterfront home this summer! Welcome home to this waterfront property in the Eastern Shore’s premier golf course community of Prospect Bay. Set on just over an acre overlooking Little Greenwood Creek, this home offers peaceful views, spacious living areas, and direct water access. From the moment you enter, the welcoming foyer with coat closet opens to a bright living room with large windows plus a stone fireplace, and a dining area that overlooks the backyard and water, creating a light-filled space ideal for everyday living and entertaining. The remodeled eat-in kitchen features abundant natural light, granite countertops, and direct access to the deck, where you can enjoy relaxing water views or dine outdoors. The home’s thoughtful layout continues on the lower level with an additional living area, half bathroom, laundry room, and convenient access to the spacious three-car garage. Sliding doors off the lower living area lead directly to the backyard and patio, seamlessly connecting indoor and outdoor living. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with beautiful water views, a walk-in closet, double vanity, and an electric fireplace that adds a cozy touch to the space. Situated on a large lot, the backyard provides plenty of room for outdoor entertaining and offers the potential for a pool overlooking the water. The recently redone pier allows for easy access to Little Greenwood Creek and the Chesapeake Bay, making this an excellent opportunity for those who enjoy waterfront living and boat rides to the Narrows, Saint Michaels, Annapolis, and beyond. Prospect Bay community offers an array of amenities, including an 18-hole golf course, a clubhouse with a members-only restaurant and bar, a marina with a launch, a pool, tennis and pickleball courts, a playground, and year-round social activities. Here, every day feels like a vacation.

MAJOR PRICE IMPROVEMENT! Just in time to enjoy your Prospect Bay waterfront home this summer! Welcome home to this waterfront property in the Eastern Shore’s premier golf course community of Prospect Bay. Set on just over an acre overlooking Little Greenwood Creek, this home offers peaceful views, spacious living areas, and direct water access. From the moment you enter, the welcoming foyer with coat closet opens to a bright living room with large windows plus a stone fireplace, and a dining area that overlooks the backyard and water, creating a light-filled space ideal for everyday living and entertaining. The remodeled eat-in kitchen features abundant natural light, granite countertops, and direct access to the deck, where you can enjoy relaxing water views or dine outdoors. The home’s thoughtful layout continues on the lower level with an additional living area, half bathroom, laundry room, and convenient access to the spacious three-car garage. Sliding doors off the lower living area lead directly to the backyard and patio, seamlessly connecting indoor and outdoor living. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with beautiful water views, a walk-in closet, double vanity, and an electric fireplace that adds a cozy touch to the space. Situated on a large lot, the backyard provides plenty of room for outdoor entertaining and offers the potential for a pool overlooking the water. The recently redone pier allows for easy access to Little Greenwood Creek and the Chesapeake Bay, making this an excellent opportunity for those who enjoy waterfront living and boat rides to the Narrows, Saint Michaels, Annapolis, and beyond. Prospect Bay community offers an array of amenities, including an 18-hole golf course, a clubhouse with a members-only restaurant and bar, a marina with a launch, a pool, tennis and pickleball courts, a playground, and year-round social activities. Here, every day feels like a vacation.

40 Greenwood Shls, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,100,000

Two Story Coastal Design on the Water! 4 bedroom 3.5 Bath, Nestled in a picturesque waterfront community offering a perfect blend of comfort, style and serenity. Home is designed and built by owner (a custom home builder) for waterfront living, coastal charm with numerous upgrades throughout this energy efficient home. Includes two car garage with workshop area and second floor above garage designed for office space or one bedroom apartment with a separate entry! Primary bedroom has waterfront view, while two bedrooms have balconies overlooking solarium on South side of home (Passive Solar Heat) Open Concept Living: The light filled living area facing East and the Chester River features large windows that invite natural light. Featuring gas fireplace and tile flooring in solarium. Spacious first floor open area includes kitchen, dining room, living room flowing into solarium. Private outdoor space: 75+ Feet of Shoreline! Step outside to your own private oasis for Spring, Summer and Fall living on screen porch, large covered deck for relaxing and entertaining. Boat dock for storing boats on lifts and room for fishing and crabbing. Sandy beach for swimming and sunbathing. large stone fire pit near waters edge for year round relaxation and enjoyment. Roof replaced in 2022

Two Story Coastal Design on the Water! 4 bedroom 3.5 Bath, Nestled in a picturesque waterfront community offering a perfect blend of comfort, style and serenity. Home is designed and built by owner (a custom home builder) for waterfront living, coastal charm with numerous upgrades throughout this energy efficient home. Includes two car garage with workshop area and second floor above garage designed for office space or one bedroom apartment with a separate entry! Primary bedroom has waterfront view, while two bedrooms have balconies overlooking solarium on South side of home (Passive Solar Heat) Open Concept Living: The light filled living area facing East and the Chester River features large windows that invite natural light. Featuring gas fireplace and tile flooring in solarium. Spacious first floor open area includes kitchen, dining room, living room flowing into solarium. Private outdoor space: 75+ Feet of Shoreline! Step outside to your own private oasis for Spring, Summer and Fall living on screen porch, large covered deck for relaxing and entertaining. Boat dock for storing boats on lifts and room for fishing and crabbing. Sandy beach for swimming and sunbathing. large stone fire pit near waters edge for year round relaxation and enjoyment. Roof replaced in 2022

902 Long Point Rd, Grasonville

Listing courtesy of Kevin Dey Realty. Contact:

Selling Office: Greater Annapolis Realty.

$980,000

This meticulously renovated and maintained home checks all the boxes - inside and outside! Enjoy an oversized saltwater heated pool [20x44] with custom waterfalls and new liner. Entertain year-round in the expansive screened gazebo complete with a kitchen, firepit, and projector home theater with surround sound. Additional family-friendly features include adjustable basketball hoop (glass backboard), adorable custom-built treehouse with zip line, and a second screened gazebo with hot tub and seating and hammocks. Inside, the main level has an open-concept gourmet kitchen and great room space with cedar plank vaulted ceiling and skylights. There’s also a game room, complete with claw-foot billiard table that conveys. Upstairs, the large primary suite features a transom for extra daylight as well as an ensuite bath with dedicated makeup vanity, bubbler tub, and walk-in closet with custom shelving system. Three additional bedrooms share a well-appointed hall bath. This home has been lovingly maintained and upgraded by the current owners for 22 years including: Hybrid high-efficiency hot water tank (2023) Dual-zone HVAC systems replaced (2021) Fiber optic WiFi upgrade (2024) Crawl space encapsulation with dehumidifier ($25k investment) Whole house water filtration system (2025) Notable exterior upgrades include updated siding, windows, exterior doors, plus a composite front porch and custom garage door. Backing to the 10th fairway, this home is close enough to the community clubhouse for walks to your next pickleball match, round of golf, swim team practice/meets for the kids, or dinner at the restaurant. Just a bit farther, you’ll find the amazing marina providing direct access to the Eastern Bay. Don’t wait to enjoy this rare slice of Eastern Shore paradise - book your showing now!

This meticulously renovated and maintained home checks all the boxes - inside and outside! Enjoy an oversized saltwater heated pool [20x44] with custom waterfalls and new liner. Entertain year-round in the expansive screened gazebo complete with a kitchen, firepit, and projector home theater with surround sound. Additional family-friendly features include adjustable basketball hoop (glass backboard), adorable custom-built treehouse with zip line, and a second screened gazebo with hot tub and seating and hammocks. Inside, the main level has an open-concept gourmet kitchen and great room space with cedar plank vaulted ceiling and skylights. There’s also a game room, complete with claw-foot billiard table that conveys. Upstairs, the large primary suite features a transom for extra daylight as well as an ensuite bath with dedicated makeup vanity, bubbler tub, and walk-in closet with custom shelving system. Three additional bedrooms share a well-appointed hall bath. This home has been lovingly maintained and upgraded by the current owners for 22 years including: Hybrid high-efficiency hot water tank (2023) Dual-zone HVAC systems replaced (2021) Fiber optic WiFi upgrade (2024) Crawl space encapsulation with dehumidifier ($25k investment) Whole house water filtration system (2025) Notable exterior upgrades include updated siding, windows, exterior doors, plus a composite front porch and custom garage door. Backing to the 10th fairway, this home is close enough to the community clubhouse for walks to your next pickleball match, round of golf, swim team practice/meets for the kids, or dinner at the restaurant. Just a bit farther, you’ll find the amazing marina providing direct access to the Eastern Bay. Don’t wait to enjoy this rare slice of Eastern Shore paradise - book your showing now!

4 Fairway Is, Grasonville

Listing courtesy of Redfin Corp. Contact:

Selling Office: Non Subscribing Office.

$965,000

A Waterfront Retreat on the Chester River! Wake up to glowing Sunrises, unwind to painted Sunsets and savor the Peaceful rhythm of life on the Waters of the Chester River. This beautifully renovated Home offers 75 feet of waterfront and a rare lot‑and‑a‑half setting comfortably outside the flood zone, giving you both serenity and security. Inside, the Home feels bright and welcoming from the moment you step in! With 4 Bedrooms, including a spacious primary en‑suite, and newly renovated Bathrooms, every space has been thoughtfully Updated for comfort and ease. The heart of the Home is the stunning Chef’s Kitchen, where a Large Quartz island invites gathering and conversation with Picturesque Views of the Water! A Wolf gas Cooktop, Brizo Vegetable Sink, Wolf Steam Convection Wall Oven, Bosch Microwave Drawer, Ceramic Farm Sink, Stainless Steel Appliances, Spice Drawer and leathered Granite countertops make cooking a true joy! Custom (Friel Lumber) Walnut Cabinetry with soft close and pull-out drawers along with Hardwood floors add timeless charm throughout. Downstairs, the cozy Family Room becomes the perfect gathering spot with its Wood‑burning stove, custom Wainscoting and a Quartz ledge that frames the Water Views like Artwork. Additional highlights include Custom Closets, Recessed Lighting, Ceiling Fans and a spacious Laundry Room. Updated white Vinyl Board-and-Batten Siding with cylinder lighting create a mesmerizing view as you come home by boat or walking back to the house from a night on the Pier! New high‑end black "Marvin" Casement windows fill the home with natural light, while a New Trane HVAC System keeps everything comfortable year‑round. Step outside and you’ll find a wraparound Teak Deck overlooking the Water, an ideal place for morning coffee, evening wine and enjoying all of those Crab Feasts! The yard is a Gardener’s delight, with mature Cherry Blossoms, a Fig Tree, a White Peach Tree, raised Garden Beds and Grapevines draped over an Italian‑inspired Arbor. Three outdoor Sheds and a Dock Box provide plenty of storage for tools, gardening and waterfront gear. The 130' Pier with L-Deck is ready for your adventures, complete with Copper capped Pilings, High Speed Boat Lift, Jet Ski/SUP/small boat Lift, Swim Ladder and Lighting Stations with water and electricity! Whether you love Crabbing, Fishing, Boating, or simply watching the River drift by, this property brings Waterfront Living to Life! Osprey, Blue Heron, Green Heron, Bald Eagles, Purple Martins, Dolphins, Buffleheads, Mallards, Rockfish, Blue Crabs and many more Wildlife will keep you entertained throughout the Seasons! The Chester River Beach Community adds to the charm with events like a 4th of July Parade, Chili cook‑off, Easter Egg Hunt, Santa visits, Holiday Lights contest, Halloween festivities and Movie nights in the Park! You’re also just a short Boat ride to the Narrows for Waterfront Dining, Rock Hall for your crab feasts and St. Michaels for all the shopping and Maritime fun! Take a quick bike ride, walk or run to the Kent Island Cross Trail and an easy drive to local Restaurants, Boutiques, Parks, Beaches and Marinas. A turnkey Waterfront haven with deep water, sweeping panoramic views and thoughtful upgrades throughout... this is the Waterfront Lifestyle you’ve been Dreaming of!

4 Beds ⋅ 2 Baths

A Waterfront Retreat on the Chester River! Wake up to glowing Sunrises, unwind to painted Sunsets and savor the Peaceful rhythm of life on the Waters of the Chester River. This beautifully renovated Home offers 75 feet of waterfront and a rare lot‑and‑a‑half setting comfortably outside the flood zone, giving you both serenity and security. Inside, the Home feels bright and welcoming from the moment you step in! With 4 Bedrooms, including a spacious primary en‑suite, and newly renovated Bathrooms, every space has been thoughtfully Updated for comfort and ease. The heart of the Home is the stunning Chef’s Kitchen, where a Large Quartz island invites gathering and conversation with Picturesque Views of the Water! A Wolf gas Cooktop, Brizo Vegetable Sink, Wolf Steam Convection Wall Oven, Bosch Microwave Drawer, Ceramic Farm Sink, Stainless Steel Appliances, Spice Drawer and leathered Granite countertops make cooking a true joy! Custom (Friel Lumber) Walnut Cabinetry with soft close and pull-out drawers along with Hardwood floors add timeless charm throughout. Downstairs, the cozy Family Room becomes the perfect gathering spot with its Wood‑burning stove, custom Wainscoting and a Quartz ledge that frames the Water Views like Artwork. Additional highlights include Custom Closets, Recessed Lighting, Ceiling Fans and a spacious Laundry Room. Updated white Vinyl Board-and-Batten Siding with cylinder lighting create a mesmerizing view as you come home by boat or walking back to the house from a night on the Pier! New high‑end black "Marvin" Casement windows fill the home with natural light, while a New Trane HVAC System keeps everything comfortable year‑round. Step outside and you’ll find a wraparound Teak Deck overlooking the Water, an ideal place for morning coffee, evening wine and enjoying all of those Crab Feasts! The yard is a Gardener’s delight, with mature Cherry Blossoms, a Fig Tree, a White Peach Tree, raised Garden Beds and Grapevines draped over an Italian‑inspired Arbor. Three outdoor Sheds and a Dock Box provide plenty of storage for tools, gardening and waterfront gear. The 130' Pier with L-Deck is ready for your adventures, complete with Copper capped Pilings, High Speed Boat Lift, Jet Ski/SUP/small boat Lift, Swim Ladder and Lighting Stations with water and electricity! Whether you love Crabbing, Fishing, Boating, or simply watching the River drift by, this property brings Waterfront Living to Life! Osprey, Blue Heron, Green Heron, Bald Eagles, Purple Martins, Dolphins, Buffleheads, Mallards, Rockfish, Blue Crabs and many more Wildlife will keep you entertained throughout the Seasons! The Chester River Beach Community adds to the charm with events like a 4th of July Parade, Chili cook‑off, Easter Egg Hunt, Santa visits, Holiday Lights contest, Halloween festivities and Movie nights in the Park! You’re also just a short Boat ride to the Narrows for Waterfront Dining, Rock Hall for your crab feasts and St. Michaels for all the shopping and Maritime fun! Take a quick bike ride, walk or run to the Kent Island Cross Trail and an easy drive to local Restaurants, Boutiques, Parks, Beaches and Marinas. A turnkey Waterfront haven with deep water, sweeping panoramic views and thoughtful upgrades throughout... this is the Waterfront Lifestyle you’ve been Dreaming of!

816 Chester River Dr, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: RE/MAX Realty Group.

$955,000

Nestled on 1.32 peaceful acres along scenic Little Greenwood Creek, this waterfront residence offers a sense of calm from the moment you arrive. Surrounded by nature and gently bordered by water, this home blends comfort with effortless living. Step inside to rich hardwood floors that flow throughout, setting a warm and inviting tone. The living room, designed with custom ceiling and gas fireplace, feels both elegant and welcoming—an ideal setting for relaxed evenings and lingering conversations. From here, the home unfolds seamlessly into a sunlit kitchen and family room, where expansive windows bring the outdoors in. Designed for both everyday living and entertaining, this bright and spacious kitchen features a five-burner gas stove, Granite counter tops, a pantry, and a breakfast bar that subtly defines the adjoining family area. Crown molding and chair railing grace the separate dining room providing an elegant backdrop for gatherings and special occasions. The versatile main-level office offers flexibility to suit your needs—whether as a productive workspace, cozy den, or guest bedroom. The addition of a new full bath with a walk-in shower enhances both its convenience and functionality. Upstairs, the gracious primary serves as a private retreat that is complemented by an equally gracious primary bath featuring a soaking tub, walk-in shower, double vanities, and a generous walk-in closet. Outdoor living is equally enticing. A Trex deck and screened porch create inviting spaces to relax or entertain while enjoying the peaceful nature views. And just beyond the lawn, a private pier awaits—perfect for quiet mornings on the water, spontaneous kayak adventures, or evenings spent watching the sky change colors. Located in the waterfront community of Prospect Bay, offering resort-style amenities—including golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant—this remarkable property captures the very best of Chesapeake living in a serene, nature filled setting.

Nestled on 1.32 peaceful acres along scenic Little Greenwood Creek, this waterfront residence offers a sense of calm from the moment you arrive. Surrounded by nature and gently bordered by water, this home blends comfort with effortless living. Step inside to rich hardwood floors that flow throughout, setting a warm and inviting tone. The living room, designed with custom ceiling and gas fireplace, feels both elegant and welcoming—an ideal setting for relaxed evenings and lingering conversations. From here, the home unfolds seamlessly into a sunlit kitchen and family room, where expansive windows bring the outdoors in. Designed for both everyday living and entertaining, this bright and spacious kitchen features a five-burner gas stove, Granite counter tops, a pantry, and a breakfast bar that subtly defines the adjoining family area. Crown molding and chair railing grace the separate dining room providing an elegant backdrop for gatherings and special occasions. The versatile main-level office offers flexibility to suit your needs—whether as a productive workspace, cozy den, or guest bedroom. The addition of a new full bath with a walk-in shower enhances both its convenience and functionality. Upstairs, the gracious primary serves as a private retreat that is complemented by an equally gracious primary bath featuring a soaking tub, walk-in shower, double vanities, and a generous walk-in closet. Outdoor living is equally enticing. A Trex deck and screened porch create inviting spaces to relax or entertain while enjoying the peaceful nature views. And just beyond the lawn, a private pier awaits—perfect for quiet mornings on the water, spontaneous kayak adventures, or evenings spent watching the sky change colors. Located in the waterfront community of Prospect Bay, offering resort-style amenities—including golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant—this remarkable property captures the very best of Chesapeake living in a serene, nature filled setting.

26 Greenwood Shls, Grasonville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Unrepresented.

$890,000

Welcome to this fabulous residence in the coveted Prospect Bay community of Grasonville, where timeless Cape Cod charm meets comfort, space, and an exceptional lifestyle. Thoughtfully designed and beautifully maintained, this picturesque home offers the perfect blend of elegance and functionality. The home features four generously sized bedrooms, including a highly desirable private guest or au pair suite above the garage with its own separate entrance, ideal for visitors, extended family, or flexible living arrangements. The primary suite is a true retreat, complete with a cozy fireplace that adds warmth and character. At the heart of the home is an inviting screened porch designed for effortless entertaining and everyday relaxation, where family and friends will naturally gather while enjoying views of the expansive backyard. The enormous backyard offers exceptional privacy and versatility, featuring an oversized storage shed, play equipment, and double rear gates for convenient access. Storage is abundant throughout the home, with multiple under-eaves storage areas, spacious closets, a 2.5-car garage, and a large storage shed, providing ample room for all your belongings as well as the water toys and equipment needed to fully enjoy life near the Bay. Perfectly positioned just moments from the water’s edge and the renowned Prospect Bay Country Club, residents enjoy a vibrant lifestyle within this premier golf and waterfront community. Centered around the meticulously maintained 18-hole championship golf course and private marina, the community offers year-round resort-style amenities, including dining, tennis, pickleball, a swimming pool, and an active calendar of social and private events. Ideally located just 25 minutes from Annapolis, Easton, and St. Michaels and only an hour from Washington, D.C. and Baltimore, this exceptional home offers the perfect balance of accessibility and serene Eastern Shore living.

Welcome to this fabulous residence in the coveted Prospect Bay community of Grasonville, where timeless Cape Cod charm meets comfort, space, and an exceptional lifestyle. Thoughtfully designed and beautifully maintained, this picturesque home offers the perfect blend of elegance and functionality. The home features four generously sized bedrooms, including a highly desirable private guest or au pair suite above the garage with its own separate entrance, ideal for visitors, extended family, or flexible living arrangements. The primary suite is a true retreat, complete with a cozy fireplace that adds warmth and character. At the heart of the home is an inviting screened porch designed for effortless entertaining and everyday relaxation, where family and friends will naturally gather while enjoying views of the expansive backyard. The enormous backyard offers exceptional privacy and versatility, featuring an oversized storage shed, play equipment, and double rear gates for convenient access. Storage is abundant throughout the home, with multiple under-eaves storage areas, spacious closets, a 2.5-car garage, and a large storage shed, providing ample room for all your belongings as well as the water toys and equipment needed to fully enjoy life near the Bay. Perfectly positioned just moments from the water’s edge and the renowned Prospect Bay Country Club, residents enjoy a vibrant lifestyle within this premier golf and waterfront community. Centered around the meticulously maintained 18-hole championship golf course and private marina, the community offers year-round resort-style amenities, including dining, tennis, pickleball, a swimming pool, and an active calendar of social and private events. Ideally located just 25 minutes from Annapolis, Easton, and St. Michaels and only an hour from Washington, D.C. and Baltimore, this exceptional home offers the perfect balance of accessibility and serene Eastern Shore living.

322 Prospect Bay Dr W, Grasonville

Listing courtesy of EXP Realty, LLC. Contact:

Welcome to this beautifully remodeled one-story home in the highly sought-after Prospect Bay community. From the moment you step inside, you’ll be impressed by the open floor plan, vaulted ceilings with skylights, and a stunning gourmet kitchen designed for both everyday living and entertaining. The upgraded kitchen features a gas cooktop, double oven with warming drawer, granite countertops, abundant cabinetry, a walk-in pantry, and a stylish wine bar. Natural hickory hardwood flooring flows throughout the home, complemented by a four-season sunroom overlooking the spacious backyard and golf course. Outdoor living is a dream with a large deck, hot tub, fire pit, and heated saltwater pool—perfect for relaxing or hosting guests year-round. The home offers four generously sized bedrooms and three full bathrooms. The primary suite includes a walk-in closet and spa-like bath with heated tile floors, walk-in shower, and soaking tub. A second primary bedroom on the opposite side of the home provides added privacy with its own full bath and walk-in closet. Meticulously maintained and beautifully landscaped, this property also offers access to all the amenities of Prospect Bay Golf & Country Club, including an 18-hole golf course, pool, tennis and pickleball courts, and a clubhouse with restaurant, bar, and grill. A rare opportunity—this home truly has it all.

$889,000

Welcome to this beautifully remodeled one-story home in the highly sought-after Prospect Bay community. From the moment you step inside, you’ll be impressed by the open floor plan, vaulted ceilings with skylights, and a stunning gourmet kitchen designed for both everyday living and entertaining. The upgraded kitchen features a gas cooktop, double oven with warming drawer, granite countertops, abundant cabinetry, a walk-in pantry, and a stylish wine bar. Natural hickory hardwood flooring flows throughout the home, complemented by a four-season sunroom overlooking the spacious backyard and golf course. Outdoor living is a dream with a large deck, hot tub, fire pit, and heated saltwater pool—perfect for relaxing or hosting guests year-round. The home offers four generously sized bedrooms and three full bathrooms. The primary suite includes a walk-in closet and spa-like bath with heated tile floors, walk-in shower, and soaking tub. A second primary bedroom on the opposite side of the home provides added privacy with its own full bath and walk-in closet. Meticulously maintained and beautifully landscaped, this property also offers access to all the amenities of Prospect Bay Golf & Country Club, including an 18-hole golf course, pool, tennis and pickleball courts, and a clubhouse with restaurant, bar, and grill. A rare opportunity—this home truly has it all.

19 Greenwood Shls, Grasonville

Listing courtesy of TTR Sotheby's International Realty. Contact:

Welcome to this beautifully upgraded home at the Enclave in Prospect Bay, the Eastern Shore’s premier golf course community, offering main-level living, thoughtful design, and premium finishes throughout. Perfectly situated on a premium lot, this home blends comfort, style, and functionality both inside and out. Located on a private lot next to the golf cart path with access to Prospect Bay’s 18-hole golf course, you are greeted by a welcoming covered front porch as you arrive. The main level features a spacious primary suite along with two additional bedrooms and two full baths, providing convenient single-level living. The primary suite showcases elegant tray ceilings and a luxurious ensuite bath with a frameless glass shower. Upstairs, a versatile loft with LVP flooring and surround sound offers flexible living space and includes a third full bath, giving it the potential to serve as an office, guest suite, or recreation room. The upgraded kitchen is a standout, featuring enhanced cabinetry, KitchenAid appliances, under-cabinet lighting, and a stand-alone ice machine, making it as functional as it is beautiful. The kitchen opens to the living room and a dining area overlooking the paver patio and the 11th hole of Prospect Bay’s golf course. Also located on this level is a spacious office with barn doors. With direct access to the garage, the conveniently located laundry room continues the upscale finishes with upgraded cabinetry and granite countertops. Designed with both style and entertaining in mind, the home features luxury vinyl plank flooring throughout the main living areas and primary bedroom, tray ceilings in the primary bedroom, dining room, kitchen, and living room, and crown molding in all main-level bedrooms and living spaces. Stylish board and batten molding and a custom wall mural in the main hallway and main-level office add distinctive character. Smart and modern touches include motorized blinds and a surround sound system in both the living room and loft. The two car garage is fully finished and thoughtfully upgraded, featuring complete interior painting, custom epoxy flooring, a bump-out for your golf car and built-in shelving for additional storage. Above the garage, extended pull-down stairs provide convenient access to additional storage space. Outdoor living is just as impressive, with a sealed and coated front porch and a paver patio with a gas-lit fire pit, perfect for relaxing evenings or entertaining guests. The community maintains the gardens and lawn, offering a true turn-key experience. Located within the exclusive Enclave at Prospect Bay, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this golf course-view property offers an unmatched lifestyle in one of Maryland’s most prestigious communities.

$860,000

Welcome to this beautifully upgraded home at the Enclave in Prospect Bay, the Eastern Shore’s premier golf course community, offering main-level living, thoughtful design, and premium finishes throughout. Perfectly situated on a premium lot, this home blends comfort, style, and functionality both inside and out. Located on a private lot next to the golf cart path with access to Prospect Bay’s 18-hole golf course, you are greeted by a welcoming covered front porch as you arrive. The main level features a spacious primary suite along with two additional bedrooms and two full baths, providing convenient single-level living. The primary suite showcases elegant tray ceilings and a luxurious ensuite bath with a frameless glass shower. Upstairs, a versatile loft with LVP flooring and surround sound offers flexible living space and includes a third full bath, giving it the potential to serve as an office, guest suite, or recreation room. The upgraded kitchen is a standout, featuring enhanced cabinetry, KitchenAid appliances, under-cabinet lighting, and a stand-alone ice machine, making it as functional as it is beautiful. The kitchen opens to the living room and a dining area overlooking the paver patio and the 11th hole of Prospect Bay’s golf course. Also located on this level is a spacious office with barn doors. With direct access to the garage, the conveniently located laundry room continues the upscale finishes with upgraded cabinetry and granite countertops. Designed with both style and entertaining in mind, the home features luxury vinyl plank flooring throughout the main living areas and primary bedroom, tray ceilings in the primary bedroom, dining room, kitchen, and living room, and crown molding in all main-level bedrooms and living spaces. Stylish board and batten molding and a custom wall mural in the main hallway and main-level office add distinctive character. Smart and modern touches include motorized blinds and a surround sound system in both the living room and loft. The two car garage is fully finished and thoughtfully upgraded, featuring complete interior painting, custom epoxy flooring, a bump-out for your golf car and built-in shelving for additional storage. Above the garage, extended pull-down stairs provide convenient access to additional storage space. Outdoor living is just as impressive, with a sealed and coated front porch and a paver patio with a gas-lit fire pit, perfect for relaxing evenings or entertaining guests. The community maintains the gardens and lawn, offering a true turn-key experience. Located within the exclusive Enclave at Prospect Bay, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this golf course-view property offers an unmatched lifestyle in one of Maryland’s most prestigious communities.

167 Masters Way, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Compass.

$860,000

Seller to pay the $5000 initiation fee for the Buyers! Welcome to your move-in ready retreat in Prospect Bay, the Eastern Shore's premier golf community! This beautifully maintained home offers a wooded setting that backs to the 12th hole. It combines timeless design with extensive updates and thoughtful spaces for everyday living and entertaining. All located in one of the most popular golf communities on the Eastern Shore, offering resort style amenities for members. As you walk towards the front entrance, you'll be greeted by a welcoming front porch that overlooks your front yard at the quiet end of Fairway Island. A separate office or formal living room is tucked just off the main entrance, with a convenient coat closet and powder room located on the other side. The main level features a spacious primary suite with a bonus sitting room that opens to the rear deck and a completely remodeled primary bathroom. The heart of the home is the family room with soaring two-story ceilings, a wood fireplace, and abundant natural light, flowing seamlessly into the oversized screened porch — perfect for morning coffee, outdoor dining, or unwinding in the evenings. The kitchen was remodeled in 2023 and features a large window overlooking the private backyard, granite counters, updated lighting and appliances, and a walk-in pantry with custom built-ins. Off the kitchen, you’ll find a formal dining room that could easily be converted to a bonus office or room. The garage has direct access to the laundry room that is tucked away by the kitchen. Upstairs, there are three generously sized bedrooms with walk-in closets, one offering access to a partially finished attic space—ideal for storage or creating an additional room. The full bathroom upstairs has also been updated. Outdoor living is easy with a rear paver patio and pathway connecting to the paved driveway, mature landscaping, and private backyard. The oversized screened porch and new primary bedroom deck provide multiple ways to enjoy the setting. Extensive updates ensure peace of mind: oversized screened porch, French drains, sump pumps, irrigation system, and roof (2013); HVAC (2014); kitchen and bath renovations, new appliances, custom pantry, alarm system, and garage/laundry doors (2023); and a full suite of 2025 improvements including new windows, doors, flooring, paint, gutters, lighting, driveway sealing, landscaping, garage systems, and more. Every detail—inside and out—has been thoughtfully maintained or upgraded, making this home truly turnkey and ready for its next chapter. Schedule your tour today! Prospect Bay is the premier golf community on the Eastern Shore offering 18-hole course, pickle ball, tennis, private clubhouse with restaurant and bar, driving range, pool, and more!

Seller to pay the $5000 initiation fee for the Buyers! Welcome to your move-in ready retreat in Prospect Bay, the Eastern Shore's premier golf community! This beautifully maintained home offers a wooded setting that backs to the 12th hole. It combines timeless design with extensive updates and thoughtful spaces for everyday living and entertaining. All located in one of the most popular golf communities on the Eastern Shore, offering resort style amenities for members. As you walk towards the front entrance, you'll be greeted by a welcoming front porch that overlooks your front yard at the quiet end of Fairway Island. A separate office or formal living room is tucked just off the main entrance, with a convenient coat closet and powder room located on the other side. The main level features a spacious primary suite with a bonus sitting room that opens to the rear deck and a completely remodeled primary bathroom. The heart of the home is the family room with soaring two-story ceilings, a wood fireplace, and abundant natural light, flowing seamlessly into the oversized screened porch — perfect for morning coffee, outdoor dining, or unwinding in the evenings. The kitchen was remodeled in 2023 and features a large window overlooking the private backyard, granite counters, updated lighting and appliances, and a walk-in pantry with custom built-ins. Off the kitchen, you’ll find a formal dining room that could easily be converted to a bonus office or room. The garage has direct access to the laundry room that is tucked away by the kitchen. Upstairs, there are three generously sized bedrooms with walk-in closets, one offering access to a partially finished attic space—ideal for storage or creating an additional room. The full bathroom upstairs has also been updated. Outdoor living is easy with a rear paver patio and pathway connecting to the paved driveway, mature landscaping, and private backyard. The oversized screened porch and new primary bedroom deck provide multiple ways to enjoy the setting. Extensive updates ensure peace of mind: oversized screened porch, French drains, sump pumps, irrigation system, and roof (2013); HVAC (2014); kitchen and bath renovations, new appliances, custom pantry, alarm system, and garage/laundry doors (2023); and a full suite of 2025 improvements including new windows, doors, flooring, paint, gutters, lighting, driveway sealing, landscaping, garage systems, and more. Every detail—inside and out—has been thoughtfully maintained or upgraded, making this home truly turnkey and ready for its next chapter. Schedule your tour today! Prospect Bay is the premier golf community on the Eastern Shore offering 18-hole course, pickle ball, tennis, private clubhouse with restaurant and bar, driving range, pool, and more!

29 Fairway Is, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Taylor Properties.

$849,000

NEW PRICE! Won't last long! From the moment you arrive, this exceptional home is sure to impress. Beautifully renovated and impeccably maintained, it feels fresh, modern, and anything but 28 years old. Located in the sought-after Prospect Bay community, this remarkable property offers water access, amenities galore, and the relaxed atmosphere of country-club living on Maryland’s Eastern Shore. A brick walkway and steps lead to the beautiful front porch and an impressive foyer with soaring ceilings, designer paint, and elegant board-and-batten detailing. The dramatic sightline extends through the great room to a wall of windows and two sets of glass French doors opening to the inviting screened porch. The modern eat-in chef’s kitchen is a showstopper, featuring quartz countertops, glass-front cabinetry, abundant storage, and a charming bay-window dining area. Wide-plank, wood-look, porcelain tile flooring flows throughout the main living areas, offering the beauty of wood with exceptional durability. Just off the kitchen, the spacious mudroom includes front-loading laundry machines, a utility sink, cabinetry, generous counter space, and convenient access to the two-car side-load garage. At the heart of the home, the breathtaking great room features soaring ceilings, board-and-batten walls, a wood-burning fireplace, and a dramatic wall of windows overlooking the lush backyard. Glass French doors lead to the expansive screened porch with wood flooring and high ceilings—an idyllic setting for morning coffee, relaxed dinners, and effortless entertaining. Beyond the porch, a spacious paver patio overlooks the peaceful, beautifully landscaped yard, enclosed by a newer white picket fence. The main level also offers an elegant formal dining room and three generously sized bedrooms, including the luxurious primary suite. The primary retreat features a walk-in closet and spa-inspired bath with dual vanities, porcelain tile flooring, a frameless glass walk-in shower with marble walls, and on-trend lighting and hardware. Gorgeous hardwood stairs lead to the upper-level overlook, where wide-plank engineered hardwood flooring continues throughout two additional bedrooms and a beautifully renovated full bath with a glass-enclosed walk-in shower and porcelain tile flooring. The flexible five-bedroom layout provides exceptional space for guests, home offices, hobbies, and/or multigenerational living. Outside, the private and beautifully landscaped lot is equally impressive. A charming backyard shed has been customized with an automatic garage-style door to accommodate a golf cart, while the expansive driveway provides parking for four or more vehicles in addition to the two-car garage. Peaceful, private, and polished from top to bottom, this extraordinary home offers gracious indoor-outdoor living in a community designed for recreation, relaxation, and life near the water. This is more than a home—it is the Eastern Shore lifestyle you have been waiting for.

5 Beds ⋅ 3 Baths

NEW PRICE! Won't last long! From the moment you arrive, this exceptional home is sure to impress. Beautifully renovated and impeccably maintained, it feels fresh, modern, and anything but 28 years old. Located in the sought-after Prospect Bay community, this remarkable property offers water access, amenities galore, and the relaxed atmosphere of country-club living on Maryland’s Eastern Shore. A brick walkway and steps lead to the beautiful front porch and an impressive foyer with soaring ceilings, designer paint, and elegant board-and-batten detailing. The dramatic sightline extends through the great room to a wall of windows and two sets of glass French doors opening to the inviting screened porch. The modern eat-in chef’s kitchen is a showstopper, featuring quartz countertops, glass-front cabinetry, abundant storage, and a charming bay-window dining area. Wide-plank, wood-look, porcelain tile flooring flows throughout the main living areas, offering the beauty of wood with exceptional durability. Just off the kitchen, the spacious mudroom includes front-loading laundry machines, a utility sink, cabinetry, generous counter space, and convenient access to the two-car side-load garage. At the heart of the home, the breathtaking great room features soaring ceilings, board-and-batten walls, a wood-burning fireplace, and a dramatic wall of windows overlooking the lush backyard. Glass French doors lead to the expansive screened porch with wood flooring and high ceilings—an idyllic setting for morning coffee, relaxed dinners, and effortless entertaining. Beyond the porch, a spacious paver patio overlooks the peaceful, beautifully landscaped yard, enclosed by a newer white picket fence. The main level also offers an elegant formal dining room and three generously sized bedrooms, including the luxurious primary suite. The primary retreat features a walk-in closet and spa-inspired bath with dual vanities, porcelain tile flooring, a frameless glass walk-in shower with marble walls, and on-trend lighting and hardware. Gorgeous hardwood stairs lead to the upper-level overlook, where wide-plank engineered hardwood flooring continues throughout two additional bedrooms and a beautifully renovated full bath with a glass-enclosed walk-in shower and porcelain tile flooring. The flexible five-bedroom layout provides exceptional space for guests, home offices, hobbies, and/or multigenerational living. Outside, the private and beautifully landscaped lot is equally impressive. A charming backyard shed has been customized with an automatic garage-style door to accommodate a golf cart, while the expansive driveway provides parking for four or more vehicles in addition to the two-car garage. Peaceful, private, and polished from top to bottom, this extraordinary home offers gracious indoor-outdoor living in a community designed for recreation, relaxation, and life near the water. This is more than a home—it is the Eastern Shore lifestyle you have been waiting for.

330 Prospect Bay Dr W, Grasonville

Listing courtesy of Samson Properties. Contact:

Selling Office: Builder Solutions Realty.

$849,000

Make your dream lifestyle a reality! MOTIVATED SELLERS HAVE FOUND THEIR HOME OF CHOICE! Bring your offer! With two primary suites, a renovated in-ground pool, more than an acre of privacy, and extensive updates throughout, 350 Prospect Bay Drive offers one of the best opportunities in its price range. Schedule your showing and bring your offer! Welcome to 350 Prospect Bay Drive, where resort-style living meets everyday comfort on a private 1.02-acre lot in the sought-after community of Prospect Bay. This beautifully updated 5-bedroom, 3.5-bath home offers over 2,700 square feet of thoughtfully designed living space, including two spacious primary suites—a rare feature ideal for multigenerational living, extended guests, or private owner retreats. Inside, soaring cathedral ceilings and an open, light-filled floor plan create an inviting atmosphere. The updated kitchen features refreshed cabinetry, granite countertops, GE refrigerator, double wall ovens, Bosch dishwasher, range hood, and luxury vinyl plank flooring throughout the main living areas. A renovated bonus room provides the perfect home office, hobby room, or flex space for today's lifestyle. Recent improvements offer peace of mind, including a new HVAC system, updated electrical, renovated hall bath, newer chimney liner, updated gutters and downspouts, fresh exterior paint, new garage door, storm doors, lighting, front walkway, fencing, and an architectural shingle roof approximately 10 years old. Step outside to your own private backyard oasis featuring a recently renovated Sylvan concrete in-ground pool, expansive paver patio, mature trees, professional landscaping, and plenty of space to entertain, relax, or simply enjoy the peaceful Eastern Shore setting. Prospect Bay offers exceptional amenities, including a marina, golf course, clubhouse, swimming pool, tennis courts, and more—all just minutes from the Bay Bridge for an easy commute to Annapolis, Baltimore, and Washington, D.C. Move in before summer ends and start enjoying your own private pool! This is a rare opportunity to own one of Prospect Bay's best values with space, privacy, and an incredible lifestyle! Very well maintained and one-year home waranty for added peace of mind.

Make your dream lifestyle a reality! MOTIVATED SELLERS HAVE FOUND THEIR HOME OF CHOICE! Bring your offer! With two primary suites, a renovated in-ground pool, more than an acre of privacy, and extensive updates throughout, 350 Prospect Bay Drive offers one of the best opportunities in its price range. Schedule your showing and bring your offer! Welcome to 350 Prospect Bay Drive, where resort-style living meets everyday comfort on a private 1.02-acre lot in the sought-after community of Prospect Bay. This beautifully updated 5-bedroom, 3.5-bath home offers over 2,700 square feet of thoughtfully designed living space, including two spacious primary suites—a rare feature ideal for multigenerational living, extended guests, or private owner retreats. Inside, soaring cathedral ceilings and an open, light-filled floor plan create an inviting atmosphere. The updated kitchen features refreshed cabinetry, granite countertops, GE refrigerator, double wall ovens, Bosch dishwasher, range hood, and luxury vinyl plank flooring throughout the main living areas. A renovated bonus room provides the perfect home office, hobby room, or flex space for today's lifestyle. Recent improvements offer peace of mind, including a new HVAC system, updated electrical, renovated hall bath, newer chimney liner, updated gutters and downspouts, fresh exterior paint, new garage door, storm doors, lighting, front walkway, fencing, and an architectural shingle roof approximately 10 years old. Step outside to your own private backyard oasis featuring a recently renovated Sylvan concrete in-ground pool, expansive paver patio, mature trees, professional landscaping, and plenty of space to entertain, relax, or simply enjoy the peaceful Eastern Shore setting. Prospect Bay offers exceptional amenities, including a marina, golf course, clubhouse, swimming pool, tennis courts, and more—all just minutes from the Bay Bridge for an easy commute to Annapolis, Baltimore, and Washington, D.C. Move in before summer ends and start enjoying your own private pool! This is a rare opportunity to own one of Prospect Bay's best values with space, privacy, and an incredible lifestyle! Very well maintained and one-year home waranty for added peace of mind.

350 Prospect Bay Dr W, Grasonville

Listing courtesy of CENTURY 21 New Millennium. Contact:

Selling Office: Gunther-McClary Real Estate.

$837,000

Buyers, get ready... Coveted Prospect Bay has a new beauty that is sure to turn heads! Thoughtful updates include new roof and hvac in 2023, complete kitchen remodel that is stunning (I'm talking removing walls and all!), new fence and deck and more! Backing to the golf course gives you scenic views with wild life on full display which can be enjoyed from the new deck and the modified open air living space (formerly a screened porch). Inside, the new kitchen is the HUB of the home with its generous island that is perfect for gatherings and entertaining. Main living room is anchored by propane fireplace and huge views of the golf course. Home office or sitting room and formal dining room, too. A total of 3 bedrooms (primary suite) and 2 full baths plus 2 car garage with interior access provides ample space to enjoy your 'Shore Life.'

3 Beds ⋅ 3 Baths

Buyers, get ready... Coveted Prospect Bay has a new beauty that is sure to turn heads! Thoughtful updates include new roof and hvac in 2023, complete kitchen remodel that is stunning (I'm talking removing walls and all!), new fence and deck and more! Backing to the golf course gives you scenic views with wild life on full display which can be enjoyed from the new deck and the modified open air living space (formerly a screened porch). Inside, the new kitchen is the HUB of the home with its generous island that is perfect for gatherings and entertaining. Main living room is anchored by propane fireplace and huge views of the golf course. Home office or sitting room and formal dining room, too. A total of 3 bedrooms (primary suite) and 2 full baths plus 2 car garage with interior access provides ample space to enjoy your 'Shore Life.'

19 Prospect Bay Dr W, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: RE/MAX United Real Estate.

$820,000

This charming ranch-style home in the desirable Prospect Bay community offers a perfect blend of comfort and elegance. With 4 spacious bedrooms and 3 full baths, the traditional floor plan features a cozy family room off the gourmet kitchen, ideal for gatherings. Enjoy upgraded countertops and a pantry, complemented by modern stainless steel appliances and huge center island. The large 3 Season room offers great flex space and views of the course. Enjoy the benefits of a tankless hot water, too! Step outside to a serene 1.01-acre lot with a rear yard, perfect for outdoor activities. The expansive deck invites you to relax while taking in stunning views of the nearby golf course. Community amenities include a refreshing pool and easy access to Prospect Bay, where you can enjoy canoeing, kayaking, and fishing. Conveniently located less than 10 miles from the airport, this home also boasts an oversized attached garage and ample driveway parking. Experience the warmth of this inviting residence, where every detail is designed for comfort and enjoyment.

This charming ranch-style home in the desirable Prospect Bay community offers a perfect blend of comfort and elegance. With 4 spacious bedrooms and 3 full baths, the traditional floor plan features a cozy family room off the gourmet kitchen, ideal for gatherings. Enjoy upgraded countertops and a pantry, complemented by modern stainless steel appliances and huge center island. The large 3 Season room offers great flex space and views of the course. Enjoy the benefits of a tankless hot water, too! Step outside to a serene 1.01-acre lot with a rear yard, perfect for outdoor activities. The expansive deck invites you to relax while taking in stunning views of the nearby golf course. Community amenities include a refreshing pool and easy access to Prospect Bay, where you can enjoy canoeing, kayaking, and fishing. Conveniently located less than 10 miles from the airport, this home also boasts an oversized attached garage and ample driveway parking. Experience the warmth of this inviting residence, where every detail is designed for comfort and enjoyment.

5 Prospect Bay Dr W, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$800,000

Great price improvement! Welcome to The Enclave at Prospect Bay, where this former model home showcases the sought-after “Pebble Beach” floor plan with thoughtful upgrades and timeless details, backing directly to the 18-hole golf course. Designed for both everyday living and entertaining, the home features three first floor bedrooms, three and a half bathrooms, and a spacious walk-up “sky basement” with a full bath—ideal as a fourth bedroom, office, or media room. The chef’s kitchen offers Quartz countertops, wall oven, cooktop, ceramic tile backsplash, pantry, and a large island that opens to the dining area and family room. There is a bonus coffee or wine bar with mini fridge, stylish glass cabinets, and additional storage located off the kitchen. In the living room, a custom fireplace with built-ins creates a warm focal point, while expansive windows and plantation shutters throughout the home invite natural light. The main-level primary suite includes a spa-like bath with dual vanities, a walk-in shower, and private water closet. Two additional bedrooms and a versatile bonus room provide flexible living space. Step outside to a spacious patio overlooking the 11th hole—perfect for entertaining or simply enjoying the views. The fenced yard is beautifully landscaped with flourishing gardens and an in-ground sprinkler system, while the HOA maintains the yard for a low-maintenance lifestyle. Additional highlights include a mudroom/laundry room off the two-car garage and efficient upgrades such as the Rinnai tankless water heater. Living in Prospect Bay means access to an array of community amenities including an 18-hole golf course, clubhouse with dining, marina, pool, tennis and pickleball courts, and year-round social activities. Here, every day feels like a vacation.

Great price improvement! Welcome to The Enclave at Prospect Bay, where this former model home showcases the sought-after “Pebble Beach” floor plan with thoughtful upgrades and timeless details, backing directly to the 18-hole golf course. Designed for both everyday living and entertaining, the home features three first floor bedrooms, three and a half bathrooms, and a spacious walk-up “sky basement” with a full bath—ideal as a fourth bedroom, office, or media room. The chef’s kitchen offers Quartz countertops, wall oven, cooktop, ceramic tile backsplash, pantry, and a large island that opens to the dining area and family room. There is a bonus coffee or wine bar with mini fridge, stylish glass cabinets, and additional storage located off the kitchen. In the living room, a custom fireplace with built-ins creates a warm focal point, while expansive windows and plantation shutters throughout the home invite natural light. The main-level primary suite includes a spa-like bath with dual vanities, a walk-in shower, and private water closet. Two additional bedrooms and a versatile bonus room provide flexible living space. Step outside to a spacious patio overlooking the 11th hole—perfect for entertaining or simply enjoying the views. The fenced yard is beautifully landscaped with flourishing gardens and an in-ground sprinkler system, while the HOA maintains the yard for a low-maintenance lifestyle. Additional highlights include a mudroom/laundry room off the two-car garage and efficient upgrades such as the Rinnai tankless water heater. Living in Prospect Bay means access to an array of community amenities including an 18-hole golf course, clubhouse with dining, marina, pool, tennis and pickleball courts, and year-round social activities. Here, every day feels like a vacation.

115 Masters Way, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

$800,000

Enjoy a waterfront country club lifestyle with the privacy of wooded views at 4 Bunkers Court! This beautifully updated and private creek front home is tucked away on a wooded 1.53 acre cul-de-sac lot at the top of Little Greenwood Creek in the sought after waterfront golf course community of Prospect Bay. From soaring vaulted ceilings and over $100k of recent thoughtful upgrades throughout, this home combines comfort, style, and space indoors and out. Step inside to a welcoming foyer and formal dining room with updated lighting. The showstopper of the home is the stunning family room featuring vaulted wood planked ceilings and a striking stone fireplace, an architectural focal point that adds warmth and character. The updated kitchen is a chef's delight with new stainless steel Frigidaire Gallery appliances, granite countertops, freshly installed tile backsplash, new flooring, and a sleek hood vent. A cozy breakfast nook with custom built-ins offers extra storage and bar countertop seating. Just off the kitchen, you’ll find a new mudroom and laundry area with two additional storage closets and a newly added powder room, all connecting to the oversized two-car garage for everyday convenience. The main level offers three bedrooms and two full bathrooms, including a serene primary suite with private patio access, two closets, and a fully updated en suite featuring a walk-in glass enclosed shower with overhead and wall mounted shower heads, and a double vanity with modern finishes. Upstairs, a spiral staircase leads to a spacious and versatile loft ideal as a fourth bedroom, office, or entertaining space. This grand loft includes a game and TV area, pool table, full bathroom with designer tile and a glass shower door, and a custom-built bar area with a beverage fridge, microwave, sink, cabinetry, and backsplash perfect for hosting guests in style. Outside, step onto your private bluestone patio and hot tub, surrounded by the natural beauty of your wooded lot. The sellers have explored the potential of building a boardwalk to the creek with a floating dock buyers to verify offering exciting possibilities for enjoying the waterfront setting. Living in Prospect Bay means more than just a beautiful home, it’s a lifestyle. Enjoy first class amenities including a championship 18 hole golf course, tennis and pickleball courts, outdoor pool, clubhouse with dining, social events, boat basin, and more. Whether you're hosting in the open concept living spaces, relaxing in your upstairs retreat, or soaking in the serenity of your private wooded backyard, 4 Bunkers Court is the perfect place to call home!

Enjoy a waterfront country club lifestyle with the privacy of wooded views at 4 Bunkers Court! This beautifully updated and private creek front home is tucked away on a wooded 1.53 acre cul-de-sac lot at the top of Little Greenwood Creek in the sought after waterfront golf course community of Prospect Bay. From soaring vaulted ceilings and over $100k of recent thoughtful upgrades throughout, this home combines comfort, style, and space indoors and out. Step inside to a welcoming foyer and formal dining room with updated lighting. The showstopper of the home is the stunning family room featuring vaulted wood planked ceilings and a striking stone fireplace, an architectural focal point that adds warmth and character. The updated kitchen is a chef's delight with new stainless steel Frigidaire Gallery appliances, granite countertops, freshly installed tile backsplash, new flooring, and a sleek hood vent. A cozy breakfast nook with custom built-ins offers extra storage and bar countertop seating. Just off the kitchen, you’ll find a new mudroom and laundry area with two additional storage closets and a newly added powder room, all connecting to the oversized two-car garage for everyday convenience. The main level offers three bedrooms and two full bathrooms, including a serene primary suite with private patio access, two closets, and a fully updated en suite featuring a walk-in glass enclosed shower with overhead and wall mounted shower heads, and a double vanity with modern finishes. Upstairs, a spiral staircase leads to a spacious and versatile loft ideal as a fourth bedroom, office, or entertaining space. This grand loft includes a game and TV area, pool table, full bathroom with designer tile and a glass shower door, and a custom-built bar area with a beverage fridge, microwave, sink, cabinetry, and backsplash perfect for hosting guests in style. Outside, step onto your private bluestone patio and hot tub, surrounded by the natural beauty of your wooded lot. The sellers have explored the potential of building a boardwalk to the creek with a floating dock buyers to verify offering exciting possibilities for enjoying the waterfront setting. Living in Prospect Bay means more than just a beautiful home, it’s a lifestyle. Enjoy first class amenities including a championship 18 hole golf course, tennis and pickleball courts, outdoor pool, clubhouse with dining, social events, boat basin, and more. Whether you're hosting in the open concept living spaces, relaxing in your upstairs retreat, or soaking in the serenity of your private wooded backyard, 4 Bunkers Court is the perfect place to call home!

4 Bunkers Ct, Grasonville

Listing courtesy of Washington Fine Properties. Contact:

Selling Office: Real Broker, LLC - Annapolis.

110 Channel Marker Way Unit 203, Grasonville

$795,000

This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded boat slip - #49 - just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded boat slip - #49 - just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

110 Channel Marker Way Unit 203, Grasonville

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Eastern Shore Real Estate, LLC.

$785,000

A BOATER'S DELIGHT, this waterfront rancher in Chester River Beach is a small slice of paradise! Enjoy deep, protected water (5ft mlw) and tranquil views of Winchester Creek. As you enter the home, you'll be captivated by the open concept kitchen and living room with expansive water views. The updated kitchen showcases white cabinets and granite countertops. The fully conditioned four season room is perfect for enjoying the views all year long and has brand new high quality windows and slider door! Features 3 bedrooms, 2 full bathrooms and an expansive 2 car garage that's large enough to fit a 25 foot boat w/ trailer inside. The primary ensuite bathroom has been gorgeously updated with floor to ceiling Italian tile. Brand new wood grain tile is featured throughout the main living areas. New roof, new HVAC, and new appliances! The pier features a 15,000 lb boat lift and deep water! Chester River Beach features a community waterfront park, picnic area and pavilion as well as a boat launch and community pier with boat slips. Enjoy the convenience of being minutes from the Kent Narrows dining and entertaining experiences by car or boat! 10 minutes to the Bay Bridge! Schedule your showing today!

3 Beds ⋅ 2 Baths

A BOATER'S DELIGHT, this waterfront rancher in Chester River Beach is a small slice of paradise! Enjoy deep, protected water (5ft mlw) and tranquil views of Winchester Creek. As you enter the home, you'll be captivated by the open concept kitchen and living room with expansive water views. The updated kitchen showcases white cabinets and granite countertops. The fully conditioned four season room is perfect for enjoying the views all year long and has brand new high quality windows and slider door! Features 3 bedrooms, 2 full bathrooms and an expansive 2 car garage that's large enough to fit a 25 foot boat w/ trailer inside. The primary ensuite bathroom has been gorgeously updated with floor to ceiling Italian tile. Brand new wood grain tile is featured throughout the main living areas. New roof, new HVAC, and new appliances! The pier features a 15,000 lb boat lift and deep water! Chester River Beach features a community waterfront park, picnic area and pavilion as well as a boat launch and community pier with boat slips. Enjoy the convenience of being minutes from the Kent Narrows dining and entertaining experiences by car or boat! 10 minutes to the Bay Bridge! Schedule your showing today!

644 Chester River Beach Rd, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$755,000

Welcome to 902 Oyster Cove, a beautifully updated 3-bedroom, 3.5-bath townhome in one of the area's most desirable waterfront communities. Rarely available and thoughtfully positioned for year-round enjoyment, this home offers a truly exceptional feature set, including a deeded boat slip and an attached garage, an uncommon combination within Oyster Cove. Inside, you’ll find a bright, refreshed interior with modern finishes, abundant natural light, and an open-concept layout designed for both everyday living and entertaining. The main level showcases marina views, a spacious kitchen, and seamless flow between the dining and living areas. Each bedroom features its own private en-suite bath, providing the comfort and privacy of three full suites. Beyond the home, Oyster Cove delivers a true resort-style experience. Residents enjoy a waterfront pool and clubhouse, marina access, kayak storage, scenic walking paths, and breathtaking sunsets that define life on the Shore. From your boat slip, cruise the Chester River or the open waters of the Chesapeake Bay, then dock just minutes away at Kent Narrows to enjoy premier waterfront dining and vibrant marina views.

Welcome to 902 Oyster Cove, a beautifully updated 3-bedroom, 3.5-bath townhome in one of the area's most desirable waterfront communities. Rarely available and thoughtfully positioned for year-round enjoyment, this home offers a truly exceptional feature set, including a deeded boat slip and an attached garage, an uncommon combination within Oyster Cove. Inside, you’ll find a bright, refreshed interior with modern finishes, abundant natural light, and an open-concept layout designed for both everyday living and entertaining. The main level showcases marina views, a spacious kitchen, and seamless flow between the dining and living areas. Each bedroom features its own private en-suite bath, providing the comfort and privacy of three full suites. Beyond the home, Oyster Cove delivers a true resort-style experience. Residents enjoy a waterfront pool and clubhouse, marina access, kayak storage, scenic walking paths, and breathtaking sunsets that define life on the Shore. From your boat slip, cruise the Chester River or the open waters of the Chesapeake Bay, then dock just minutes away at Kent Narrows to enjoy premier waterfront dining and vibrant marina views.

902 Oyster Cove Dr, Grasonville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Core Maryland Real Estate LLC.

$739,000

Prestigious Prospect Bay – Golf Course and Waterfront Living at Its Finest! This stunning Colonial sits directly on the golf course with breathtaking views of the 18th tee, a rare opportunity to own in one of the Eastern Shore’s most sought-after waterfront communities. Inside, you’ll find 4 spacious bedrooms and 2.5 beautifully appointed baths with over 2300 sq ft!! . The gourmet kitchen is a showstopper! Gorgeous granite countertops, under-cabinet lighting, and a farmhouse sink perfectly positioned to overlook the lush backyard and fairway. A cozy sitting area with a fireplace creates the perfect spot for morning coffee, while the large eat-in dining space offers panoramic golf course views. The main level bedroom provides flexibility for guests, an office, or a den. The family room boasts custom trim work, adding charm and character. Upstairs, hardwood floors run throughout. The primary suite is bright and spacious with a walk-in closet and a renovated spa-like bathroom featuring tile floors and a custom vanity. Bedrooms two and three are equally impressive, both oversized with huge closets. The backyard is an entertainer’s dream! Screened-in porch, expansive deck, and wide-open yard all facing the golf course. The property also includes a detached 2-car garage, providing extra storage and parking space. Living in Prospect Bay means enjoying an unmatched resort lifestyle with a private clubhouse featuring a restaurant and party room, a sparkling community pool with a snack shack, pickleball and tennis courts, a pro shop and driving range, plus a private marina and boat ramp with water access to Prospect Bay and the area’s best waterfront restaurants. Here, you’ll have golf, boating, dining, and social events right at your doorstep. You’ll never want to leave!