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$789,000
3 Beds ⋅ 3 Baths
Professional Photos Coming Soon! Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living area. Double porches provide the perfect place to relax and take in breathtaking sunset views over the creek. Positioned on a desirable corner lot, the home also features a fenced backyard, spacious deck, and hardscape patio—ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A rear-entry two-car garage with a large parking pad provides ample space for residents and guests. Gibson’s Grant is conveniently located near waterfront dining, shopping, and the Cross Island Trail, with easy access to the Bay Bridge for commuting or exploring all that the Eastern Shore has to offer. Experience the perfect blend of waterfront community living, everyday convenience, and the relaxed Shore lifestyle.

402 Macum Creek Dr, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$550,000
5 Beds ⋅ 4 Baths
Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this residence is designed for comfort and functionality. Enjoy cozy evenings by one of the two fireplaces. With new windows, the natural light floods the traditional floor plan, enhanced by recessed lighting and wood floors throughout. The entry-level bedroom offers convenience, while the walk-in closets provide ample storage. Step outside to your personal oasis with an in-ground pool (new pool pump), ideal for summer relaxation and entertaining. With a generous 0.39-acre lot and side-entry garage, this home combines space and style.

326 Castle Marina Rd, Chester

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$649,990
2 Beds ⋅ 2 Baths
Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area offers a spacious and functional space for lounging. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

641 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$350,000
2 Beds ⋅ 2 Baths
Your Island Getaway Is Waiting! Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bedroom Island home may be just what you’ve been waiting for! Start your mornings—or wind down your evenings—on the inviting front porch, where you can swing with the little ones, rock to your favorite playlist, and enjoy the laid-back Island lifestyle. Inside the spacious living room features a wood stove, creating the perfect spot for cozy winter nights. The bright, well-appointed kitchen offers a center island, granite countertops, stainless steel appliances, abundant cabinetry, and a pantry—plenty of room for preparing family meals or entertaining friends. Just off the kitchen, the screened porch is ready for three-season enjoyment. Imagine crab feasts with family and friends, relaxing evenings, or cheering on your favorite team while enjoying the crisp fall air! Outside, the huge, privately fenced rear yard offers plenty of space for the kids to play, pets to roam, or everyone to gather. Multiple sheds provide convenient storage for all your crabbing, fishing, boating, and outdoor gear. Upstairs, you’ll find two spacious bedrooms plus a walk-up attic with endless possibilities. Use it for additional storage, a home office, hobby space—or transform it into an additional bedroom to suit your needs. Whether you’re looking for a year-round home, a weekend retreat, or your own slice of Island living, this one offers comfort, space, charm, and plenty of potential at a great price. PLUS...the boat ramp is just 2 mins away which means fresh seafood is what's for dinner! Come see it for yourself—this Island gem won’t last long!

200 Church St, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$944,900
3 Beds ⋅ 3 Baths
Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place. Situated on a premium corner lot, this impressive home features 3 bedrooms, a dedicated home office, a spacious second-floor loft and a 3-car garage, including a tandem bay with EV charger. Inside, custom details immediately set it apart, including decorative molding in the foyer and primary bedroom, upgraded chandeliers in the foyer and dining room, custom window shades and a beautiful stone propane fireplace. The kitchen showcases K. Hovnanian's upgraded Looks package with crisp white cabinetry and upgraded Thermador appliances, complemented by reverse osmosis at the kitchen sink and a whole-house water filtration system. Additional features include a Rinnai tankless water heater, two-zone HVAC with propane backup and a whole-home surge protector. Outdoor living is ready to enjoy with a paver patio, propane grill hookup, irrigation system and upgraded landscaping—no waiting for a new yard to grow in or projects to be completed. Best of all, the location puts the Four Seasons lifestyle right outside your door. Enjoy easy access to the community's pickleball courts, clubhouse, indoor and outdoor pools, fitness center, walking trails, pier, kayak launch and more. Why wait to build when you can move right into a nearly new Kerr with the premium lot, upgrades, landscaping and finishing touches already done? 275 Warbler Way delivers exceptional value and an easy, move-in-ready Eastern Shore lifestyle.

275 Warbler Way, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$400,000
5 Beds ⋅ 4 Baths
List price is Opening Bid at the Online auction to be conducted on Auctioneers website. - Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and versatility of 1868 Roberta Drive in Chester, Maryland, a custom-built home offering 5 bedrooms, 3.5 bathrooms, multiple living areas, abundant storage, and no HOA. Conveniently located just minutes from Route 50 and the Chesapeake Bay Bridge, this property combines generous proportions with a layout designed for comfortable everyday living and entertaining. The main level makes an immediate impression with 12-foot ceilings and oversized 6-foot windows, creating bright, open living spaces throughout. The floor plan includes a spacious family room, vaulted morning room, sunroom, and an eat-in kitchen that serves as the heart of the home. The kitchen is equipped with granite countertops, a large center island, pantry, and ample cabinet and workspace. The home’s 5-bedroom, 3.5-bath configuration provides plenty of flexibility. The primary suite features a tray ceiling and private bath with a custom-tiled shower and double vanity. Four additional bedrooms are complemented by two Jack-and-Jill-style bathrooms, offering a functional arrangement for family, guests, home offices, or additional flex space. Outdoor living is another highlight, with an impressive 800± square-foot wraparound deck providing plenty of room for grilling, dining, entertaining, and relaxing. Additional features include: • Hardwood and tile flooring • Roman blinds and wood shutters • New HVAC system • Finished garage • Dedicated laundry room with New washer and dryer • Approximately 4-foot crawl-space ceiling height • Numerous custom builder upgrades • No HOA With its impressive bedroom count, expansive living areas, oversized deck, substantial storage, and convenient Chester location, 1868 Roberta Drive offers bidders a unique opportunity to purchase a custom Eastern Shore home and make it their own. Don’t miss your opportunity to bid!

1868 Roberta Dr, Chester

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

$1,250,000
3 Beds ⋅ 3 Baths
Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality. Inside, you'll find a dedicated home office and stylish engineered hardwood and tile flooring throughout, creating a seamless and low-maintenance living space. Large windows invite natural light and showcase the home's tranquil waterfront setting. Outdoor living is just as impressive, featuring two maintenance-free decks, a patio ideal for grilling and entertaining, and a fenced backyard perfect for pets, play, or simply enjoying the beautiful surroundings. Whether hosting friends or relaxing with a morning coffee, this home offers multiple spaces to take in the peaceful water views. Boating enthusiasts will appreciate the private pier equipped with both water and electric service, while the pier decking was replaced last year, providing added value and peace of mind. Enjoy easy access to boating, fishing, crabbing, kayaking, and all the activities that make waterfront living so special. Conveniently located on Kent Island near shopping, dining, marinas, and commuter routes, this exceptional waterfront property offers the perfect blend of luxury, comfort, and Chesapeake Bay lifestyle. 3 Bedrooms | 2.5 Baths | Main-Level Primary Suite | Separate Office | Waterfront on Cox Creek | Private Pier with Water & Electric | New Pier Decking (2025) | Two Maintenance-Free Decks | Grilling Patio | Fenced Backyard | Renovated Approximately 4 Years Ago

1717 Harbor Dr, Chester

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$279,900
3 Beds ⋅ 1 Baths

920 E 20th St, Chester

Listing courtesy of BHHS Fox & Roach - Chester. Contact: (484) 483-9660
$365,000
3 Beds ⋅ 2 Baths
Nestled in the quiet Mistwood Forest neighborhood, this charming home offers comfort, space, and convenience. The main level features a large primary bedroom with a private bathroom, beautiful hardwood floors, a spacious laundry room, and an open-concept kitchen and dining area—perfect for everyday living and entertaining. The home also offers generously sized bedrooms, two-zone heating and cooling, multiple attics, and abundant storage throughout. Enjoy your morning coffee surrounded by natural light in the inviting Florida room or relax on the large rear deck overlooking the expansive, fully fenced backyard. Conveniently located just minutes from shopping, dining, and everything Chester has to offer, this wonderful home is ready for its next owner. Don’t miss your opportunity to make it yours!

14519 Sonnenburg Dr, Chester

Listing courtesy of Move4Free Realty, LLC. Contact: 2023691460
$569,900
4 Beds ⋅ 3 Baths
Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the upgraded interior, every detail has been carefully considered. Step inside to a welcoming two-story foyer leading to a formal living room and separate dining area. The interior features LVP flooring (2020), ceramic tile, plush new carpet throughout the stairs/upper level (2026) and architectural details throughout including crown molding, chair rail, and wainscoting. The gourmet kitchen is the heart of the home, showcasing silestone countertops, stainless steel appliances, under-cabinet lighting, ceramic tile backsplash, a spacious island, and additional cabinetry and countertop space adjacent to the pantry. The separate breakfast area features a new sliding glass door (2025) leading to the private fenced backyard, complete with a Trex/Vinyl deck (2015), shed, extensive hardscape, and beautifully landscaped grounds. The inviting family room features a floor-to-ceiling stone gas/propane fireplace (2018) and adjacent office/storage area. Renovated main-level powder room with updated vanity and lighting (2020), laundry room with Closet America cabinetry and access to attached two-car garage with epoxy flooring (2024) and insulated, finished walls (2025). OWNER IS WILLING TO REMOVE STAIR LIFT TO UPPER LEVEL AND REPLACE WITH CARPET ON STAIRCASE. On the upper level, you'll find four generously sized bedrooms, including a spacious primary suite with a walk-in closet and private en-suite bathroom featuring dual granite vanities and a large walk-in shower. The renovated hall bathroom offers updated ceramic tile, a quartz vanity, and tub/shower combination. The second floor and stairway have also been freshly painted. Additional highlights include updated hallway, foyer, and kitchen lighting, brushed nickel door hardware and hinges throughout. The home also features 6" gutters and downspouts with gutter guards (2023), asphalt roof replaced in (2018), and driveway torn out and replaced/sealed (2024/2026). Clayborne Woods is a private neighborhood that offers a jog/walk path, community management, and trash service. Enjoy the best of Kent Island living with a location just minutes from the Chesapeake Bay Bridge, beaches, parks, boat ramps, marinas, waterfront dining, shopping, restaurants, and schools. This exceptional home combines comfort, convenience, thoughtful updates, and coastal charm. Come see for yourself what Kent Island living is all about!

233 Cross Creek Ct, Chester

Listing courtesy of Rory S. Coakley Realty, Inc.. Contact:

$1,290,000
5 Beds ⋅ 2 Baths
Waterfront homes are common on Kent Island. Waterfront acreage is not. The difference is the land -- and at 1.65 acres with 205 feet of protected shoreline, this property belongs in a conversation with the finest waterfront offerings on Kent Island, not the most common. Waterfront properties with this combination of acreage, waterfront footage, and finishes are rare at this price point. The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a cinder block barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor -- but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and has invested hundreds of thousands of dollars in improvements across sixty years of devoted stewardship. This property has never been publicly offered for sale -- until now. Situated on 1.65 acres with 205 feet of protected waterfront on Cox Creek, this is one of the largest privately held waterfront parcels remaining in Harbor View. The 75-foot private pier extends into navigable tidal water with approximately 3.5 feet at mean low tide and two boat slips. Shoreline reinforced with professional rip-rap. Flood Zone X -- outside 100-year and 500-year floodplains. The home offers approximately 2,700 sq ft of living space across two levels with an additional 700 sq ft of unfinished second & third-level expansion space. Five bedrooms, two full baths. The upper-level primary suite features hardwood floors, panoramic water views, attached full bath, walk-in closet, private coffee bar with refrigerator, and a deck overlooking the creek. Updated kitchen with granite countertops, upgraded cabinetry, and high-end appliances. 9'+ ceilings throughout. Solid cinder block construction. 200-amp electrical. Well water, public sewer. The locals once called it Keister's Folly. The next owner will call it home. Ideal for those who are seeking genuine Chesapeake waterfront with privacy, deep water access, and a property unlike anything else on the market. Be sure to download the Home Profile in the documents section for more details on the home including the history of the home.

2513 Cecil Dr, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$899,000
3 Beds ⋅ 3 Baths
Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add modern convenience throughout. The kitchen has been refreshed with new KitchenAid appliances, backsplash, under-cabinet lighting, updated fixtures and hardware, a new exhaust fan and disposal, instant hot water, and an enhanced pantry with pull-out storage. Just beyond, the mudroom adds both charm and function with brick flooring and Pottery Barn built-ins. The primary suite feels like a private retreat, featuring a completely renovated bath with a custom vanity, Kohler fixtures, and a luxurious BainUltra spa tub with chromatherapy lighting, along with added built-in closet storage. The guest bath and powder room have also been beautifully updated, while the laundry room features new cabinetry, luxury vinyl flooring, and a new GE washer and dryer. Outside, enjoy a private setting backing to trees and a quiet rear alley. Extensive professional landscaping, a drip irrigation system, landscape lighting, new pergola, and added deck railing create an inviting outdoor space for relaxing or entertaining. Even the garage has been thoughtfully upgraded with an EV charger, Elfa shelving, motion-detected lighting, fresh paint, and a GE refrigerator. Located in Gibson’s Grant, one of Kent Island’s most desirable waterfront communities, residents enjoy picturesque streets, walking trails, a community pool and clubhouse, waterfront pavilion, fishing pier, kayak launch, and beautiful views of Macum Creek and the Chester River. With its extensive 2025 renovation, private setting, and coveted Gibson’s Grant location, 148 Elinor Street offers the rare opportunity to enjoy an established coastal community with the feel and finish of a newly designed home.

148 Elinor St, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$819,900
3 Beds ⋅ 3 Baths
Located in the sought-after waterfront community of Gibson’s Grant, this beautiful Koch Homes property features the popular Ashford model, with a first-floor Primary Bedroom enhanced by a three-foot extension. A first-floor study offers flexible space for a home office, den, or possible fourth bedroom. Thoughtfully designed and exceptionally well-maintained, the home offers numerous updates and features, including a new roof installed in 2026 with a transferable manufacturer’s warranty and a new kitchen completed in 2022 featuring GE Café appliances, including a professional 36” six-burner range with convection oven, an additional oven in the island, and an Advantium speed-cook microwave. The kitchen appliances are under warranty through February 2028. The Primary Bathroom was renovated in 2019 and features heated floors, an oversized shower, and a customized makeup vanity. A Rinnai tankless hot water system provides efficient, on-demand hot water. The main level features beautiful hardwood floors, a convenient half bath, motorized window blinds in the Family Room, and a Ring security system. The home also offers a spacious basement crawl space with convenient interior access, providing valuable additional storage for seasonal items and household belongings, as well as a water-powered backup sump pump for added peace of mind. Outdoor spaces are equally inviting, with a welcoming front porch, spacious rear deck, rear patio, fenced yard, and a propane quick-connect hookup on the deck for a grill, making outdoor cooking and entertaining easy and convenient. A rear-entry two-car garage with a three-car parking pad provides ample parking. The garage includes a refrigerator, a freezer with a warranty through October 2027, a storage system, and electric bike lift with an HDTV antenna mounted on the garage roof. Upstairs are two additional bedrooms and a full bathroom, while the finished room above the garage offers flexible living, office, hobby, or recreation space and features a split-system HVAC for year-round comfort. Enjoy all that Gibson’s Grant has to offer, including water access to Macum Creek and the Chester River, a community pool, clubhouse, fitness center, kayak launch, walking trails, playgrounds, and scenic open spaces. Ideally located just minutes from the Bay Bridge, shopping, dining, and everything Kent Island has to offer, this exceptional home provides the perfect combination of quality construction, thoughtful updates, flexible living spaces, and a wonderful waterfront community lifestyle.

207 Thomas White Blvd, Chester

Listing courtesy of RE/MAX Components. Contact: 4433535281
$749,990
2 Beds ⋅ 3 Baths
Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

536 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$449,900
4 Beds ⋅ 3 Baths
Beautifully Colonial freshly painted two-car garage home in the heart of Chester! The main level showcases refinished hardwood floors throughout. Elegant columns connect the crown-molded living room to the formal dining room, featuring a tray ceiling and additional crown molding. The eat-in kitchen offers granite countertops, a subway tile backsplash, pantry, new fixtures, gas cooking, stainless-steel appliances, and sliding doors leading to an expansive 24-by-10-foot, two-tier deck. The adjoining family room features a gas fireplace and crown molding, creating a comfortable, open-concept gathering space. A convenient half bath completes the first floor. Upstairs, carpeting extends throughout the hallway and bedrooms. The spacious primary suite features a tray ceiling, walk-in closet, and spa-inspired bathroom with tile flooring, a double vanity with granite countertops, a Jacuzzi tub, and a walk-in shower with tile surround. Bedroom two includes three windows, a sitting area, and a ceiling fan. Bedroom three also offers a ceiling fan, while the generously sized fourth bedroom features two closets, a ceiling fan, and its own sitting area. The hall bathroom includes a double vanity with granite countertops, tile flooring, and a tiled tub surround. A large laundry room with tile flooring and abundant shelving adds convenience. SCHEDULE SHOWINGS THROUGH SHOWINGTIME APP ON YOUR PHONE

3455 Ivyridge Dr, Chester

Listing courtesy of Move4Free Realty, LLC. Contact: 2023691460
$409,900
3 Beds ⋅ 3 Baths
Welcome to this beautiful Higgins-built home, ideally situated on one of the largest and most picturesque lots in the Thornhill subdivision of Southbend. Set on an impressive 1.18-acre landscaped lot, this one-owner home offers a spacious party deck and a double-width paved driveway. Inside, the home’s pride of ownership is immediately apparent. The inviting living room features hardwood flooring, a vaulted ceiling, and a striking arched window. The formal dining room is enhanced by hardwood floors, crown molding, and a beautiful bay window. The spacious kitchen offers abundant cabinetry, ceramic tile flooring, and a coordinating tile backsplash. The family room includes hardwood floors, a built-in television niche, and a cozy gas fireplace. The generously sized primary suite features a recently renovated private bathroom, while the two additional bedrooms offer comfortable proportions, carpeting, and ceiling fans. Upstairs, a large hardwood-floored loft overlooks the living room and provides flexible space for a home office, media room, or sitting area. Lovingly maintained by its original owner, this exceptional home is conveniently located just minutes from Fort Lee, Richmond International Airport, shopping, and neighborhood schools around the corner SCHEDULE SHOWINGS THROUGH SHOWINGTIME APP ON YOUR PHONE.

304 Thornhill Dr, Chester

Listing courtesy of Move4Free Realty, LLC. Contact: 2023691460
$924,000
3 Beds ⋅ 3 Baths
Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining. Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers an and additional bedroom, and a second family room. Don't miss the full walk in storage area above the garage that is partially finished. More storage is available in the oversized fully finished two car garage with room for a third car or golf cart. Off the dining area is a screened-in porch and paver patio with a fire pit and out door built in grilling area. Backing to the pond, no houses behind you and views of the fountain is what makes this truly an exceptional lot and setting. The community run irrigation system Is an added bonus to this community. You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience.

214 Bayberry Dr, Chester

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$862,750
3 Beds ⋅ 2 Baths
THE SELLER WILL ACCEPT OFFERS WITH MOST FURNITURE INCLUDED. SOME SMALL DECORATIONS AND A FEW PICTURES ARE RESERVED. THE MOVING VAN IS ALREADY SCHEDULED. Be part of the fastest growing 55+ community on Maryland's Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just completed $80,000 in renovations. Most of the Furniture can be purchased for below half of what it’s value. The optional sunroom area was completely finished as additional living space. There is a massive 256 square foot rear patio with low V lighting and two raised garden beds. Another HOA area is the rear buffer and beautifully landscaped. If they have a dog, the common area next to the home is almost the size of a building lot offering exceptional privacy. FSKI club house offers resort quality from the indoor pool and gym or the outside pool in summer months. FSKI also allows you golf carts! Don’t miss this opportunity to experience resort style living at Four Seasons Kent Island.

320 Bayberry Dr, Chester

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478
$1,200,000
3 Beds ⋅ 4 Baths
The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The beautifully appointed kitchen features a range, single oven, microwave, range hood, dishwasher, French door refrigerator, stylish pendant lighting, and a coordinating tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a fresh, integrated design. LVP flooring extends across the main level for durability and style, with tile in all full baths and carpet in Bedrooms 2 and 3 for added comfort. The owner’s bath offers a spa-inspired shower with a built-in seat, handheld shower wand, and double sinks—creating a relaxing and functional daily retreat. For a full list of included features, please contact our sales representatives. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

117 Flycatcher Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$799,900
4 Beds ⋅ 3 Baths
Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

313 Thomas White Blvd, Chester

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3848
$747,900
4 Beds ⋅ 3 Baths
Welcome Home!!! Open DAILY by Appointment - Or stop by one of our OPEN HOUSES***If you're looking for the ease of primarily one-level living with flexible space for guests and hobbies, 209 Harrier Way offers the best of both worlds.*** Barely lived in and offering over $75,000 in builder upgrades, this home still feels like new, allowing you to move right in without the wait or additional costs of new construction (i.e. transfer tax split, etc). Designed for easy everyday living, the Simone model offers the convenience of having the majority of the home's daily living spaces on the main level. The gourmet kitchen, dining and living areas, screened porch, primary suite, second bedroom, office, full bath, and laundry are all thoughtfully located on the main floor. The stunning gourmet kitchen features crisp white cabinetry, a large center island, stainless steel appliances, wall oven/microwave combination, and propane gas range, flowing seamlessly into the light-filled dining and living areas. The living room is anchored by a cozy stone fireplace, while the screened porch provides a relaxing place to enjoy your morning coffee or unwind. The main-level primary suite features tray ceilings and a spa-inspired bath with dual vanities, a large walk-in shower, and an expansive walk-in closet. Upstairs, you'll find flexible bonus space including a spacious loft, two additional bedrooms, and a full bath, perfect for visiting family, hobbies, entertaining, or simply having extra space when you want it. **It's additional space when you need it, without requiring stairs for your everyday living.** The attached garage adds convenience and storage. Beyond the home, enjoy a resort-style lifestyle with incredible amenities including a 23,000-square-foot clubhouse, fitness center, indoor and outdoor pools, billiards, tennis and pickleball courts, community pier, outdoor bar, fire pit, and a full calendar of social activities. The nearby Cross Island Trail is perfect for walking, running, or biking, and you're just minutes from shopping, dining, and everything Kent Island has to offer.

209 Harrier Way, Chester

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

$868,000
4 Beds ⋅ 3 Baths
A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033
$160,000
3 Beds ⋅ 1 Baths
Completely Renovated | Bonus Room | Huge Backyard | Minutes to I-95, Philadelphia & Delaware Welcome home to this beautifully renovated 3-bedroom, 1-bath home in the heart of Chester, where modern updates meet everyday convenience. From the moment you step inside, you’ll appreciate the bright, open feel, stylish finishes, recessed lighting, updated flooring, and the pride of craftsmanship throughout. The spacious layout offers comfortable living with an additional bonus room that’s perfect for a home office, playroom, gym, guest room, or flex space to fit your lifestyle. The oversized bathroom provides plenty of room to relax, while the generous bedrooms offer comfort and versatility. Step outside to enjoy the huge backyard, providing endless possibilities for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. Conveniently located just minutes from I-95, this home offers easy access to Philadelphia, Delaware, and surrounding areas—making commuting a breeze while still enjoying the charm of a quiet residential block. Whether you’re a first-time homebuyer, looking to upgrade, or searching for a move-in-ready property, this home checks all the boxes. Property Highlights: * ✔ Completely renovated * ✔ 3 spacious bedrooms * ✔ 1 oversized bathroom * ✔ Bonus room for office, gym, or flex space * ✔ Huge backyard * ✔ Modern finishes throughout * ✔ Quiet block * ✔ Minutes to I-95, Philadelphia, and Delaware * ✔ Move-in ready Don’t miss your opportunity to own this beautifully updated home that offers space, style, and an unbeatable location. Schedule your private showing today!

925 Walnut St, Chester

Listing courtesy of Believe Realty Group. Contact:

$180,000
5 Beds ⋅ 1 Baths
Welcome to 1110 Morton Ave, Chester, PA 19013 — a spacious single-family home offering five bedrooms and one bathroom. The main level features a living room and a kitchen, with additional space in the basement for storage or flexible use. This property provides ample room for a variety of layouts and uses across its multiple bedrooms. Conveniently located in Chester, the home presents an opportunity to personalize and update to suit your needs.

1110 Morton Ave, Chester

Listing courtesy of Prosperity Real Estate & Investment Services. Contact: 8663277673
$439,999
5 Beds ⋅ 3 Baths
Charming cottage-style home on a private cul-de-sac with a spacious ½-acre lot! This beautifully maintained home blends timeless character with thoughtful modern updates. Featuring a detached garage with workshop space, concrete driveway, vinyl siding, thermal windows, and a large fenced backyard with a deck off the sunroom make this property truly special. Inside, you'll find original hardwood floors, solid wood doors, crown molding, custom built-in bookcases, and a cozy family room featuring a raised brick hearth and gas fireplace. The updated kitchen showcases new cabinetry, butcher block countertops, tile backsplash (2020), and Samsung Bespoke smart appliances (2024). The main-level primary bedroom offers convenient one-level living, while the large sunroom provides year-round enjoyment with its own HVAC, propane heater, and new carpet. Upstairs are four additional generously sized bedrooms and two baths. Recent improvements include HVAC (2021), Ecobee smart thermostat (2021), GE washer and dryer (2024), ceiling fans (2024), privacy fence (2025), new carpet in the primary bedroom and sunroom (2025), attic insulation (2026), front and storm doors (2026), and 10-year smoke/CO detectors (2026). The roof was replaced in 2009 with a 35-year warranty. With abundant storage, classic craftsmanship, and an exceptional list of updates, this move-in-ready home is one you won't want to miss!

5400 Karma Rd, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$749,000
4 Beds ⋅ 4 Baths
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

134 Richard Ingle Way, Chester

Listing courtesy of Redfin Corp. Contact: 3016586186
$899,990
3 Beds ⋅ 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

532 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$929,990
3 Beds ⋅ 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

540 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$697,900
2 Beds ⋅ 2 Baths
Assumable VA Loan available w/interest rate in 5's to qualified buyers! Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay. Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful enhancements include Hunter Douglas plantation shutters, custom California Closets in the owner's suite and second bedroom, modern ceiling fans throughout, reverse osmosis water filtration, and professionally treated energy-efficient windows that reduce UV rays and heat for year-round comfort. Beyond your front door, enjoy a true resort-style lifestyle just 45 miles from both Washington, D.C. and Baltimore. The impressive 24,000-square-foot clubhouse offers indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and an active social calendar led by a full-time lifestyle director. From kayaking, yoga, and walking clubs to mahjong, pickleball, and countless social events, there is something for everyone. Located just steps from the waterfront and minutes from historic Annapolis, this vibrant Kent Island community combines small-town charm with exceptional convenience. Enjoy easy access to Route 50, along with nearby shopping, dining, and everything that makes Chesapeake Bay living so special.

121 Merlin Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$525,000
5 Beds ⋅ 3 Baths
Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for. With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

205 Anchor Ln, Chester

Listing courtesy of Samson Properties. Contact: 7033788810