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Brimming with traditional character, architectural details, and the enduring appeal of solid brick construction, this charming three-bedroom, two-bath rambler offers exceptional one-level living in the sought-after town of Easton, Maryland. Beautifully situated on a generously sized lot along South Washington Street, the home is set well back from the road, surrounded by magnificent trees and mature landscaping. A welcoming brick walkway leads to the front entrance, where the home's delightful character continues throughout its bright, beautifully maintained interior. Gorgeous hardwood flooring, elegant crown molding, custom built-ins, and distinctive architectural details showcase the craftsmanship and timeless appeal of this classic home. Abundant windows fill the spacious living room with natural light, while a traditional wood-burning fireplace and custom built-in shelving create an inviting gathering space. A generously sized formal dining room overlooks the beautiful grounds, and the updated kitchen features granite countertops, stainless steel appliances, a separate pantry, and charming built-in shelving. Just beyond the kitchen, a versatile family room offers additional living or recreation space. Three comfortable bedrooms feature hardwood flooring and attractive recessed lighting, while two full baths include a beautifully renovated bathroom with shiplap accents, a double-sink vanity, LVP flooring, and an expansive tiled walk-in shower. Meticulously maintained, the home benefits from significant recent improvements, including a new roof with 50-year shingles, replacement windows, and gutter guards installed in 2022, along with stainless steel kitchen appliances purchased within the past five years. Outside, the picturesque backyard features magnificent shade trees, and a spacious deck for outdoor entertaining. A charming brick outbuilding with electricity, rear-entry garage, and generous off-street parking add convenience and functionality. Completing this exceptional offering is its premier location in historic Easton, approximately a mile from downtown's acclaimed restaurants, boutiques, art galleries, and cultural attractions. Nearby Idlewild Park, shopping, healthcare, and everyday conveniences further enhance the appeal of this wonderful Eastern Shore setting. Combining timeless architectural charm, thoughtful updates, beautiful grounds, and an outstanding location, this captivating brick home is truly something special. Upcoming Open Houses: Friday 11/13 (2:00-4:00), Saturday 11/14 (10:00-1:00), Sunday 11/15 (10:00-1:00)

903 S Washington St, Easton

Listing courtesy of Northrop Realty. Contact:

$11,500,000

Fairmiles, one of Talbot County’s most distinguished waterfront estates, enjoys an extraordinary setting along the coveted Miles River. This Federal-style manor blends timeless elegance with the warmth and charm of Maryland’s Eastern Shore. Rarely does an estate offer such an intimate connection to the water. The residence and waterside swimming pool are remarkably close to the protected shoreline, capturing sweeping, ever- changing river views from nearly every room. Each season unveils its own captivating beauty: summer yachts gracefully navigating the river, autumn’s brilliant palette of changing colors, the enchanting glow of Christmas trees illuminating with neighboring piers, and the fresh blossoms of spring. Together, these ever-changing scenes create a remarkable waterfront experience throughout the year. A private dock with an impressive eight feet of mean low water (MLW) depth offers exceptional opportunities for accommodating deep-draft vessels. Ideally situated between historic Easton and St. Michaels, Fairmiles combines privacy, natural beauty, and refined waterfront living with convenient access to exceptional dining, shopping, and cultural attractions. For the discerning traveler, Easton Airport is approximately ten minutes away, offering convenient private aviation access and fixed-base operator (FBO) services. By appointment only. Listing agents must accompany all showings. Do not enter the property without an appointment.

6 Beds ⋅ 7 Baths

Fairmiles, one of Talbot County’s most distinguished waterfront estates, enjoys an extraordinary setting along the coveted Miles River. This Federal-style manor blends timeless elegance with the warmth and charm of Maryland’s Eastern Shore. Rarely does an estate offer such an intimate connection to the water. The residence and waterside swimming pool are remarkably close to the protected shoreline, capturing sweeping, ever- changing river views from nearly every room. Each season unveils its own captivating beauty: summer yachts gracefully navigating the river, autumn’s brilliant palette of changing colors, the enchanting glow of Christmas trees illuminating with neighboring piers, and the fresh blossoms of spring. Together, these ever-changing scenes create a remarkable waterfront experience throughout the year. A private dock with an impressive eight feet of mean low water (MLW) depth offers exceptional opportunities for accommodating deep-draft vessels. Ideally situated between historic Easton and St. Michaels, Fairmiles combines privacy, natural beauty, and refined waterfront living with convenient access to exceptional dining, shopping, and cultural attractions. For the discerning traveler, Easton Airport is approximately ten minutes away, offering convenient private aviation access and fixed-base operator (FBO) services. By appointment only. Listing agents must accompany all showings. Do not enter the property without an appointment.

26989 Miles River Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$2,000,000

Location, location, location. This fully renovated waterfront rancher sits on a 2+ acre, park-like lot bordering Talbot Country Club, just off the Oxford Road corridor — close enough to walk to lunch at the club, private enough to forget it's there. Inside, the home lives like a boutique retreat. The kitchen and family room combine around quartz counters, stainless appliances, and custom solid wood cabinetry, opening to a living room with fireplace and reclaimed barnwood oak flooring running through the main living areas. The primary suite channels a five-star hotel — custom built-ins, a tiled zero-entry shower, and a private steam shower. A tile-floored sunroom and thoughtful ADA/aging-in-place features (32"+ doorways, 36"+ halls, roll-in shower access) round out a home built for comfort at every stage of life. The mechanicals match the finishes: whole-home generator, upgraded electrical panel, whole-home Sonos audio across six zones (garage, front porch, living room, great room, back porch, and poolside), upgraded well pump for stronger water volume throughout, and an epoxy-finished, cabinet-outfitted garage. Outside, this is a waterman's and water-lover's dream. The private dock — rebuilt larger, with new water and electric service — includes two remote-controlled boat lifts, two remote-controlled jet ski lifts, and a floating kayak launch, all set on 150 feet of frontage with 3' MLW on Trippe Creek. Crabbing is easy right off the dock. The in-ground gunite pool sits shaded by mature trees, creating a private, cooler retreat even at the height of summer, with recently replaced pumps and upgraded floating sprinkler equipment. Enjoy sunrise from the back porch and sunset from the front — with front-row seats to the eagles and osprey that nest along the creek each year, arriving as early as March. This is more than a renovation — it's a fully re-system waterfront estate, ready for its next chapter.

3 Beds ⋅ 4 Baths

Location, location, location. This fully renovated waterfront rancher sits on a 2+ acre, park-like lot bordering Talbot Country Club, just off the Oxford Road corridor — close enough to walk to lunch at the club, private enough to forget it's there. Inside, the home lives like a boutique retreat. The kitchen and family room combine around quartz counters, stainless appliances, and custom solid wood cabinetry, opening to a living room with fireplace and reclaimed barnwood oak flooring running through the main living areas. The primary suite channels a five-star hotel — custom built-ins, a tiled zero-entry shower, and a private steam shower. A tile-floored sunroom and thoughtful ADA/aging-in-place features (32"+ doorways, 36"+ halls, roll-in shower access) round out a home built for comfort at every stage of life. The mechanicals match the finishes: whole-home generator, upgraded electrical panel, whole-home Sonos audio across six zones (garage, front porch, living room, great room, back porch, and poolside), upgraded well pump for stronger water volume throughout, and an epoxy-finished, cabinet-outfitted garage. Outside, this is a waterman's and water-lover's dream. The private dock — rebuilt larger, with new water and electric service — includes two remote-controlled boat lifts, two remote-controlled jet ski lifts, and a floating kayak launch, all set on 150 feet of frontage with 3' MLW on Trippe Creek. Crabbing is easy right off the dock. The in-ground gunite pool sits shaded by mature trees, creating a private, cooler retreat even at the height of summer, with recently replaced pumps and upgraded floating sprinkler equipment. Enjoy sunrise from the back porch and sunset from the front — with front-row seats to the eagles and osprey that nest along the creek each year, arriving as early as March. This is more than a renovation — it's a fully re-system waterfront estate, ready for its next chapter.

6119 Country Club Dr, Easton

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

$775,000

Beautifully situated on an exceptional lot overlooking a picturesque pond, this spacious home in the desirable Back Creek Landing community offers gorgeous sunset views, wonderful privacy, and a peaceful setting just minutes from historic St. Michaels. Tucked away on a quiet cul-de-sac, the property enjoys a lovely natural backdrop and a sense of tranquility that makes it feel like a private retreat. With over 3,000 square feet of living space, this thoughtfully designed home features 4 bedrooms, 2.5 baths, and a comfortable, versatile floor plan ideal for both everyday living and entertaining. Highlights include a spacious primary suite, inviting family room, separate dining room, and a private office or den. The eat-in kitchen, featuring newer appliances, opens to a delightful screened porch where you can relax, enjoy the pond views, and take in the spectacular evening sunsets. Beautifully maintained and thoughtfully updated, the home features fresh interior paint, an encapsulated crawl space, and numerous upgrades and special touches throughout. Generous living spaces and an easy flow between rooms create a welcoming atmosphere, with plenty of room to gather with family and friends or simply enjoy the comforts of home. Back Creek Landing is a charming community offering a wonderful Eastern Shore lifestyle, with amenities including a community pier on San Domingo Creek, kayak racks, scenic walking trails, ponds, and a wildlife observation area. Just a short drive away, historic St. Michaels offers an exceptional selection of waterfront dining, boutique shopping, marinas, and year-round activities. From quiet mornings overlooking the pond to spectacular sunsets from the screened porch, this is a home designed for enjoying the beauty and relaxed pace of life on Maryland’s Eastern Shore

Beautifully situated on an exceptional lot overlooking a picturesque pond, this spacious home in the desirable Back Creek Landing community offers gorgeous sunset views, wonderful privacy, and a peaceful setting just minutes from historic St. Michaels. Tucked away on a quiet cul-de-sac, the property enjoys a lovely natural backdrop and a sense of tranquility that makes it feel like a private retreat. With over 3,000 square feet of living space, this thoughtfully designed home features 4 bedrooms, 2.5 baths, and a comfortable, versatile floor plan ideal for both everyday living and entertaining. Highlights include a spacious primary suite, inviting family room, separate dining room, and a private office or den. The eat-in kitchen, featuring newer appliances, opens to a delightful screened porch where you can relax, enjoy the pond views, and take in the spectacular evening sunsets. Beautifully maintained and thoughtfully updated, the home features fresh interior paint, an encapsulated crawl space, and numerous upgrades and special touches throughout. Generous living spaces and an easy flow between rooms create a welcoming atmosphere, with plenty of room to gather with family and friends or simply enjoy the comforts of home. Back Creek Landing is a charming community offering a wonderful Eastern Shore lifestyle, with amenities including a community pier on San Domingo Creek, kayak racks, scenic walking trails, ponds, and a wildlife observation area. Just a short drive away, historic St. Michaels offers an exceptional selection of waterfront dining, boutique shopping, marinas, and year-round activities. From quiet mornings overlooking the pond to spectacular sunsets from the screened porch, this is a home designed for enjoying the beauty and relaxed pace of life on Maryland’s Eastern Shore

8014 Gosling Pond Ct, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$575,000

This stunning Bungalow with a seperate commercial rental was beautifully renovated in 2020 and offers a perfect blend of modern luxury and timeless charm. With 1,168 sq. ft. of meticulously designed space in the residence, every corner of this home exudes warmth and sophistication. The renovated office building adds additional square footage. The open layout invites natural light, highlighting the exquisite craftsmanship throughout. Enjoy the seamless flow between indoor and outdoor living, perfect for entertaining or quiet evenings at home. The property features a versatile office/studio, ideal for remote work or creative pursuits. Nestled on a generous 0.19-acre lot, the lush surroundings provide a serene escape from the hustle and bustle of daily life. Parking is a breeze with ample driveway and street options. This residence is not just a home; it's a lifestyle, offering comfort, elegance, and a sense of community. Experience the joy of living in a space that has been thoughtfully updated to meet the demands of modern living while retaining its unique character. Your dream home and investment awaits!

This stunning Bungalow with a seperate commercial rental was beautifully renovated in 2020 and offers a perfect blend of modern luxury and timeless charm. With 1,168 sq. ft. of meticulously designed space in the residence, every corner of this home exudes warmth and sophistication. The renovated office building adds additional square footage. The open layout invites natural light, highlighting the exquisite craftsmanship throughout. Enjoy the seamless flow between indoor and outdoor living, perfect for entertaining or quiet evenings at home. The property features a versatile office/studio, ideal for remote work or creative pursuits. Nestled on a generous 0.19-acre lot, the lush surroundings provide a serene escape from the hustle and bustle of daily life. Parking is a breeze with ample driveway and street options. This residence is not just a home; it's a lifestyle, offering comfort, elegance, and a sense of community. Experience the joy of living in a space that has been thoughtfully updated to meet the demands of modern living while retaining its unique character. Your dream home and investment awaits!

5 S Park St S, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,285,000

Well maintained one level living on Cummings Creek. 3 BR's, 2.5 baths, DR, kitchen, waterside living room, 2 car garage, oversized screen porch. Beautiful Westerly sunset views. Pier has a boat lift, water and electric. 4 MLW with an option to extend the pier 50' to get over 5 MLW. Plenty of room to expand the footprint or add a pool. Professional Photos to Come.

Well maintained one level living on Cummings Creek. 3 BR's, 2.5 baths, DR, kitchen, waterside living room, 2 car garage, oversized screen porch. Beautiful Westerly sunset views. Pier has a boat lift, water and electric. 4 MLW with an option to extend the pier 50' to get over 5 MLW. Plenty of room to expand the footprint or add a pool. Professional Photos to Come.

8710 Cummings Rd, Wittman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$499,900

Welcome to this lovely corner-lot home in desirable Easton Club East, offering 2,342 square feet of thoughtfully designed living space in Del Webb’s popular two-story Wittman model. A welcoming entry introduces beautiful architectural details and a spacious, well-appointed floor plan designed for comfortable everyday living and effortless entertaining. The elegant formal dining room features a tray ceiling, providing a wonderful setting for gatherings and special occasions. The bright, spacious kitchen offers a center island, pantry, abundant cabinetry, and a generous casual dining area. Just beyond, the inviting great room showcases a soaring vaulted ceiling, solar tubes that fill the space with natural light, and a cozy gas fireplace. A lovely sun room provides additional space to relax and unwind, while a dedicated main-level office offers the convenience of working from home. The first-floor primary suite features a spacious walk-in closet and private bath complete with dual vanities, a walk-in shower, and a soaking tub. A second bedroom, full hall bath, and convenient laundry room complete the main level. Upstairs, a fabulous loft-style family room provides a versatile second living area, perfect for relaxing, entertaining, or accommodating guests. A third bedroom and full bath offer additional privacy and flexibility, making this level ideal for extended family or multi generational living. Outside, mature landscaping creates a lovely sense of privacy around the patio, offering a peaceful setting for outdoor enjoyment. Additional highlights include a two-car rear-loading garage, generous driveway, and a new roof installed in 2023. Residents of Easton Club East enjoy an exceptional collection of community amenities, including a clubhouse with fitness room, library, and entertainment space; outdoor swimming pool; tennis and pickleball courts; bocce ball; putting green; picnic areas; gazebos; and scenic walking trails. The community also offers a convenient location for commuting, shopping, dining, and enjoying all that the Eastern Shore has to offer. An Important Distinction: This home is located in the non-age-restricted section of Easton Club East, meaning buyers are not required to be 55 or older. Residents enjoy the same community amenities and are subject to the same HOA dues and regulations.ties.

Welcome to this lovely corner-lot home in desirable Easton Club East, offering 2,342 square feet of thoughtfully designed living space in Del Webb’s popular two-story Wittman model. A welcoming entry introduces beautiful architectural details and a spacious, well-appointed floor plan designed for comfortable everyday living and effortless entertaining. The elegant formal dining room features a tray ceiling, providing a wonderful setting for gatherings and special occasions. The bright, spacious kitchen offers a center island, pantry, abundant cabinetry, and a generous casual dining area. Just beyond, the inviting great room showcases a soaring vaulted ceiling, solar tubes that fill the space with natural light, and a cozy gas fireplace. A lovely sun room provides additional space to relax and unwind, while a dedicated main-level office offers the convenience of working from home. The first-floor primary suite features a spacious walk-in closet and private bath complete with dual vanities, a walk-in shower, and a soaking tub. A second bedroom, full hall bath, and convenient laundry room complete the main level. Upstairs, a fabulous loft-style family room provides a versatile second living area, perfect for relaxing, entertaining, or accommodating guests. A third bedroom and full bath offer additional privacy and flexibility, making this level ideal for extended family or multi generational living. Outside, mature landscaping creates a lovely sense of privacy around the patio, offering a peaceful setting for outdoor enjoyment. Additional highlights include a two-car rear-loading garage, generous driveway, and a new roof installed in 2023. Residents of Easton Club East enjoy an exceptional collection of community amenities, including a clubhouse with fitness room, library, and entertainment space; outdoor swimming pool; tennis and pickleball courts; bocce ball; putting green; picnic areas; gazebos; and scenic walking trails. The community also offers a convenient location for commuting, shopping, dining, and enjoying all that the Eastern Shore has to offer. An Important Distinction: This home is located in the non-age-restricted section of Easton Club East, meaning buyers are not required to be 55 or older. Residents enjoy the same community amenities and are subject to the same HOA dues and regulations.ties.

29709 Lyons Dr, Easton

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

$365,000

Welcome to Stoney Ridge Farm in Easton, Maryland! This 4-bedroom, 2-full-bath split-level home presents an excellent opportunity for buyers looking to make a home their own while building equity through improvements. Offering a versatile split-level floor plan, this property provides a great starting point for those ready to bring their ideas and personal touches to life. While the home could benefit from updating and cosmetic improvements, it offers the opportunity for the next owner to customize the property to their preferences and potentially reap the benefits of their own sweat equity. Whether making improvements over time or planning a more extensive renovation, the possibilities are worth exploring. Located in the established Stoney Ridge Farm neighborhood, the property offers convenient access to Easton's shopping, dining, and local amenities. For buyers seeking an opportunity to enter the Easton housing market and create value through thoughtful improvements, this home is certainly worth considering. Bring your vision and explore the potential this property has to offer!

4 Beds ⋅ 2 Baths

Welcome to Stoney Ridge Farm in Easton, Maryland! This 4-bedroom, 2-full-bath split-level home presents an excellent opportunity for buyers looking to make a home their own while building equity through improvements. Offering a versatile split-level floor plan, this property provides a great starting point for those ready to bring their ideas and personal touches to life. While the home could benefit from updating and cosmetic improvements, it offers the opportunity for the next owner to customize the property to their preferences and potentially reap the benefits of their own sweat equity. Whether making improvements over time or planning a more extensive renovation, the possibilities are worth exploring. Located in the established Stoney Ridge Farm neighborhood, the property offers convenient access to Easton's shopping, dining, and local amenities. For buyers seeking an opportunity to enter the Easton housing market and create value through thoughtful improvements, this home is certainly worth considering. Bring your vision and explore the potential this property has to offer!

29430 Corbin Pkwy, Easton

Listing courtesy of Sid Sells Maryland Realty. Contact:

$1,895,000

Discover the epitome of luxury living in this stunning Colonial home nestled in the desirable Martingham community. This exquisite residence has been freshly painted and boasts 5 spacious bedrooms and 5.5 totally updated bathrooms. The primary bath has an expansive steam shower, soaker tub and heated floors for those chilly mornings. The heart of the home features a spacious gourmet kitchen equipped with stainless steel appliances, including a Kitchen Aid refrigerator, Wolf double oven, Wolf 5 burner gas cooktop and Wolf dishwasher. Major renovations completed in 2026 include new roof with exposed copper valleys, copper gutters, windows and doors on the back of the house of the 1st floor have been replaced, new air handler on the 3rd floor, attic vent foam insulation, crawlspace has been encapsulated with sump pump and dehumidifier, irrigation and landscaping all have elevated this property to new heights, ensuring modern amenities while preserving its classic charm. Enjoy the ambience of two brick fireplaces, the convenience of an upper-floor laundry, and the tranquility of newly finished hardwood flooring throughout. The expansive private 2.34-acre lot faces the 14th hole of The Links at Perry Cabin picturesque golf course, offering a serene backdrop for outdoor gatherings. Step outside to your personal oasis, complete with a saltwater gunite pool, perfect for summer relaxation. The community enhances your lifestyle with well-maintained common areas and a waterfront picnic area for homeowners. This home is not just a residence; it's a lifestyle. There is nothing left to do but move your furniture in. Don't miss your chance to own this exceptional property!

5 Beds ⋅ 6 Baths

Discover the epitome of luxury living in this stunning Colonial home nestled in the desirable Martingham community. This exquisite residence has been freshly painted and boasts 5 spacious bedrooms and 5.5 totally updated bathrooms. The primary bath has an expansive steam shower, soaker tub and heated floors for those chilly mornings. The heart of the home features a spacious gourmet kitchen equipped with stainless steel appliances, including a Kitchen Aid refrigerator, Wolf double oven, Wolf 5 burner gas cooktop and Wolf dishwasher. Major renovations completed in 2026 include new roof with exposed copper valleys, copper gutters, windows and doors on the back of the house of the 1st floor have been replaced, new air handler on the 3rd floor, attic vent foam insulation, crawlspace has been encapsulated with sump pump and dehumidifier, irrigation and landscaping all have elevated this property to new heights, ensuring modern amenities while preserving its classic charm. Enjoy the ambience of two brick fireplaces, the convenience of an upper-floor laundry, and the tranquility of newly finished hardwood flooring throughout. The expansive private 2.34-acre lot faces the 14th hole of The Links at Perry Cabin picturesque golf course, offering a serene backdrop for outdoor gatherings. Step outside to your personal oasis, complete with a saltwater gunite pool, perfect for summer relaxation. The community enhances your lifestyle with well-maintained common areas and a waterfront picnic area for homeowners. This home is not just a residence; it's a lifestyle. There is nothing left to do but move your furniture in. Don't miss your chance to own this exceptional property!

9450 Canvasback Way, St Michaels

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

$459,900

Welcome to 8496 Colony Circle in the desirable Matthewstown Run neighborhood! This well-maintained 4-bedroom, 2.5-bath home offers a great combination of comfortable living space and outdoor amenities. The home features an updated kitchen with stainless steel appliances, a newer roof, and a welcoming front porch. Out back, you'll find a spacious rear yard with a large deck and above-ground pool, providing plenty of room for entertaining friends and family or enjoying the warmer months. Conveniently located just minutes from downtown Easton, with easy access to local shops, restaurants, schools, and other amenities. Don't miss this great opportunity to own a home in the established Matthewstown Run community!

Welcome to 8496 Colony Circle in the desirable Matthewstown Run neighborhood! This well-maintained 4-bedroom, 2.5-bath home offers a great combination of comfortable living space and outdoor amenities. The home features an updated kitchen with stainless steel appliances, a newer roof, and a welcoming front porch. Out back, you'll find a spacious rear yard with a large deck and above-ground pool, providing plenty of room for entertaining friends and family or enjoying the warmer months. Conveniently located just minutes from downtown Easton, with easy access to local shops, restaurants, schools, and other amenities. Don't miss this great opportunity to own a home in the established Matthewstown Run community!

8496 Colony Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$495,000

Welcome to 7311 Madaline Avenue in desirable Easton Club East, a Chesapeake by Del Webb community. Built by Pulte Builders, the popular Vanderbilt model offers a wonderfully flexible floor plan, generous living spaces, and a beautiful park-like setting, all of this in a well maintained home featuring a newer roof create an inviting Eastern Shore retreat. Thoughtfully designed for comfortable everyday living and entertaining, this home features nine-foot ceilings, an adaptable living and dining area, and an additional flexible living space with built-in shelving, ideal for a home office, music room, or quiet retreat. The inviting family room features a gas fireplace, built-in cabinetry, and recessed lighting, opening to a cheerful breakfast area and well-appointed kitchen with granite countertops, gas cooking, and convenient pantry storage. One of the home’s most outstanding features is its beautiful new screened-in porch, extending the living space outdoors and providing a peaceful place to relax, entertain, or simply enjoy the natural surroundings. Overlooking a picturesque, park-like setting framed by mature trees and walking path, this delightful outdoor retreat offers wonderful opportunities to appreciate the changing seasons from many areas within the home. The spacious primary suite features a tray ceiling, private bath with soaking tub and separate shower, and an exceptionally generous walk-in closet with thoughtfully designed organizers, abundant shelving, and pull-out drawers. An additional bedroom, full hall bath, and versatile office or music room provide flexibility for guests, hobbies, or working from home. A convenient laundry and mudroom area, abundant storage, and attached two-car garage complete the home’s practical amenities. Easton Club East is a beautifully established 55+ community offering an exceptional array of amenities, including an impressive clubhouse with fitness center, outdoor swimming pool, tennis and pickleball courts, bocce, walking paths, scenic ponds, and attractively maintained common areas. A full-time lifestyle director coordinates a variety of clubs, social gatherings, recreational activities, and special events, creating a welcoming and engaging community atmosphere. Lawn maintenance and snow removal add to the appeal of easy, low-maintenance living. Just minutes away, historic downtown Easton offers an outstanding selection of restaurants, charming boutiques, art galleries, and cultural attractions, including the renowned Avalon Theatre and Academy Art Museum. Quality medical facilities, shopping, and everyday conveniences are nearby, while the picturesque waterfront villages of St. Michaels and Oxford, the Chesapeake Bay, and the many recreational opportunities of Maryland’s Eastern Shore are within easy reach. Discover the wonderful combination of comfort, flexibility, natural beauty, and community at 7311 Madaline Avenue—a delightful place to enjoy your next chapter of Eastern Shore living.

2 Beds ⋅ 2 Baths

Welcome to 7311 Madaline Avenue in desirable Easton Club East, a Chesapeake by Del Webb community. Built by Pulte Builders, the popular Vanderbilt model offers a wonderfully flexible floor plan, generous living spaces, and a beautiful park-like setting, all of this in a well maintained home featuring a newer roof create an inviting Eastern Shore retreat. Thoughtfully designed for comfortable everyday living and entertaining, this home features nine-foot ceilings, an adaptable living and dining area, and an additional flexible living space with built-in shelving, ideal for a home office, music room, or quiet retreat. The inviting family room features a gas fireplace, built-in cabinetry, and recessed lighting, opening to a cheerful breakfast area and well-appointed kitchen with granite countertops, gas cooking, and convenient pantry storage. One of the home’s most outstanding features is its beautiful new screened-in porch, extending the living space outdoors and providing a peaceful place to relax, entertain, or simply enjoy the natural surroundings. Overlooking a picturesque, park-like setting framed by mature trees and walking path, this delightful outdoor retreat offers wonderful opportunities to appreciate the changing seasons from many areas within the home. The spacious primary suite features a tray ceiling, private bath with soaking tub and separate shower, and an exceptionally generous walk-in closet with thoughtfully designed organizers, abundant shelving, and pull-out drawers. An additional bedroom, full hall bath, and versatile office or music room provide flexibility for guests, hobbies, or working from home. A convenient laundry and mudroom area, abundant storage, and attached two-car garage complete the home’s practical amenities. Easton Club East is a beautifully established 55+ community offering an exceptional array of amenities, including an impressive clubhouse with fitness center, outdoor swimming pool, tennis and pickleball courts, bocce, walking paths, scenic ponds, and attractively maintained common areas. A full-time lifestyle director coordinates a variety of clubs, social gatherings, recreational activities, and special events, creating a welcoming and engaging community atmosphere. Lawn maintenance and snow removal add to the appeal of easy, low-maintenance living. Just minutes away, historic downtown Easton offers an outstanding selection of restaurants, charming boutiques, art galleries, and cultural attractions, including the renowned Avalon Theatre and Academy Art Museum. Quality medical facilities, shopping, and everyday conveniences are nearby, while the picturesque waterfront villages of St. Michaels and Oxford, the Chesapeake Bay, and the many recreational opportunities of Maryland’s Eastern Shore are within easy reach. Discover the wonderful combination of comfort, flexibility, natural beauty, and community at 7311 Madaline Avenue—a delightful place to enjoy your next chapter of Eastern Shore living.

7311 Madaline Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$679,990

Welcome to the Franklin, a beautifully designed home that pairs an open-concept layout with timeless Classic elements. Offering 3 bedrooms, 3.5 baths, and a 2.5-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with a walk-in closet. 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.

3 Beds ⋅ 4 Baths

Welcome to the Franklin, a beautifully designed home that pairs an open-concept layout with timeless Classic elements. Offering 3 bedrooms, 3.5 baths, and a 2.5-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with a walk-in closet. 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.

29488 Mason Ln, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$2,395,000

SECOND WIND is a remarkable Eastern Shore sanctuary where history, privacy, and the beauty of the water define everyday living. As noted in The Eastern Shore Dependent in 1963, “Nature provided the idyllic setting.” Set amid nearly 3 acres of magnificent landscaping, with more than 400 feet of protected and licensed shoreline, this property captures sweeping broad water views and unforgettable sunsets from almost every room. The historic c. 1800 two-story section enjoys random width Georgia pine floors. On the main level you will find a fireside den with built-in bookcases plus a private office with fireplace and two bedrooms and a full bath upstairs. The more contemporary additions include multiple living areas offering a welcoming blend of historic character and comfortable living, including living/dining room, an inviting county kitchen and a main-level primary suite with vaulted beamed ceiling and en-suite bath. The kitchen features a breakfast bar and casual dining area, opening to a patio and heated pool and spa – an inviting setting for relaxation and entertaining. A private pier and protected and licensed shoreline incorporating a living shoreline enhance the waterfront setting, while magnificent perennial gardens, an attached garage, a detached workshop with artist studio above, and several outbuildings add to the property's appeal. Recent improvements include a new roof. Lovingly maintained and exceptionally private, SECOND WIND offers a rare opportunity to own a truly distinctive waterfront property steeped in Eastern Shore history.

SECOND WIND is a remarkable Eastern Shore sanctuary where history, privacy, and the beauty of the water define everyday living. As noted in The Eastern Shore Dependent in 1963, “Nature provided the idyllic setting.” Set amid nearly 3 acres of magnificent landscaping, with more than 400 feet of protected and licensed shoreline, this property captures sweeping broad water views and unforgettable sunsets from almost every room. The historic c. 1800 two-story section enjoys random width Georgia pine floors. On the main level you will find a fireside den with built-in bookcases plus a private office with fireplace and two bedrooms and a full bath upstairs. The more contemporary additions include multiple living areas offering a welcoming blend of historic character and comfortable living, including living/dining room, an inviting county kitchen and a main-level primary suite with vaulted beamed ceiling and en-suite bath. The kitchen features a breakfast bar and casual dining area, opening to a patio and heated pool and spa – an inviting setting for relaxation and entertaining. A private pier and protected and licensed shoreline incorporating a living shoreline enhance the waterfront setting, while magnificent perennial gardens, an attached garage, a detached workshop with artist studio above, and several outbuildings add to the property's appeal. Recent improvements include a new roof. Lovingly maintained and exceptionally private, SECOND WIND offers a rare opportunity to own a truly distinctive waterfront property steeped in Eastern Shore history.

5704 Irish Creek Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$499,888

Welcome to Tilghman on Chesapeake! Discover this peaceful community in a serene setting away from the crowds of traditional beach towns, yet conveniently located near the charming waterfront town of St. Michaels and the amenities of Easton, Maryland. This beautiful Sussex floorplan features 3 bedrooms, 2 full bathrooms, cozy front porch and a 2-car garage. The home includes beautiful quartz countertops, stainless steel appliances, a large island and a spacious family room highlighted by a gas fireplace. The private owner’s retreat offers a relaxing escape, including a Venetian-style private bathroom. Complete with a new home warranty for added peace of mind, this home combines modern finishes, everyday comfort, and the appeal of Eastern Shore living. Enjoy an exceptional community lifestyle with amenities including a waterfront clubhouse, swimming pool, picnic area, and community pier. Boat slips are also available for purchase or lease, making it easy to embrace the Chesapeake Bay lifestyle.

Welcome to Tilghman on Chesapeake! Discover this peaceful community in a serene setting away from the crowds of traditional beach towns, yet conveniently located near the charming waterfront town of St. Michaels and the amenities of Easton, Maryland. This beautiful Sussex floorplan features 3 bedrooms, 2 full bathrooms, cozy front porch and a 2-car garage. The home includes beautiful quartz countertops, stainless steel appliances, a large island and a spacious family room highlighted by a gas fireplace. The private owner’s retreat offers a relaxing escape, including a Venetian-style private bathroom. Complete with a new home warranty for added peace of mind, this home combines modern finishes, everyday comfort, and the appeal of Eastern Shore living. Enjoy an exceptional community lifestyle with amenities including a waterfront clubhouse, swimming pool, picnic area, and community pier. Boat slips are also available for purchase or lease, making it easy to embrace the Chesapeake Bay lifestyle.

5648 Trafalgar Cir, Tilghman

Listing courtesy of Mary Ann Hammel. Contact:

$3,600,000

Come see a true Eastern Shore gem, set on 20 peaceful waterfront acres along Edge Creek. This beautifully renovated 4-bedroom, 4-bathroom home features all the hallmarks of a coastal getaway while providing modern, functional conveniences. Walk through the front door, and you’re met with direct water views that can be seen from virtually every room in the home. You’ll also find natural light that fills every space due to the ample window and sliding glass door installations, coupled with southwestern exposure off the back of the home. Make your way over to the well-appointed, fully renovated kitchen featuring Miele appliances. Around the corner is a first-floor primary suite with direct waterfront views, his-and-hers sink vanities, a spacious walk-in closet system with built-ins, and one of the home’s three fireplaces. Upstairs, you’ll find plenty of space for guests, including a bedroom featuring built-in bunks. On the third floor is a bonus loft area with twin walkout balconies. Across the driveway is a detached garage with two car bays, a workshop, and a storage area. Above the garage, you’ll find a separate in-law suite or apartment space with a living area, bedroom, full bathroom, and kitchenette. Around the back of the home is an entertaining space that makes for the perfect Eastern Shore weekend. A beautifully done gunite pool overlooks your 1,600 feet of shoreline. A private dock with a boat lift (insert weight capacity) provides easy access for an afternoon cruise or evening fishing expedition. With privacy from your neighbors and close proximity to historic downtown St. Michaels, this home provides the ultimate secluded Chesapeake Bay oasis.

Come see a true Eastern Shore gem, set on 20 peaceful waterfront acres along Edge Creek. This beautifully renovated 4-bedroom, 4-bathroom home features all the hallmarks of a coastal getaway while providing modern, functional conveniences. Walk through the front door, and you’re met with direct water views that can be seen from virtually every room in the home. You’ll also find natural light that fills every space due to the ample window and sliding glass door installations, coupled with southwestern exposure off the back of the home. Make your way over to the well-appointed, fully renovated kitchen featuring Miele appliances. Around the corner is a first-floor primary suite with direct waterfront views, his-and-hers sink vanities, a spacious walk-in closet system with built-ins, and one of the home’s three fireplaces. Upstairs, you’ll find plenty of space for guests, including a bedroom featuring built-in bunks. On the third floor is a bonus loft area with twin walkout balconies. Across the driveway is a detached garage with two car bays, a workshop, and a storage area. Above the garage, you’ll find a separate in-law suite or apartment space with a living area, bedroom, full bathroom, and kitchenette. Around the back of the home is an entertaining space that makes for the perfect Eastern Shore weekend. A beautifully done gunite pool overlooks your 1,600 feet of shoreline. A private dock with a boat lift (insert weight capacity) provides easy access for an afternoon cruise or evening fishing expedition. With privacy from your neighbors and close proximity to historic downtown St. Michaels, this home provides the ultimate secluded Chesapeake Bay oasis.

7116 Pea Neck Rd, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$480,000

Discover the charm of this beautifully renovated ranch-style home, set to impress with its major renovations completed in 2026. This home boasts 4 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and comfort. The open layout seamlessly connects the living areas, creating a warm atmosphere perfect for gatherings or quiet evenings at home. The heart of the home features a modern kitchen equipped white cabinets and sleek quartz countertops. Enjoy the convenience of an attached garage 2 car garage with and additional storage. The expansive lot, spanning over 0.61 acres, offers plenty of outdoor space for gardening, play, or simply enjoying the fresh air. This home was designed with a focus on comfort and functionality. Sit on the front porch and enjoy the serene views of the rural farmlands, this property is perfect for those seeking a peaceful retreat while still being close to local shopping and dining. Experience the perfect blend of modern living and timeless charm in this delightful home. Don't miss the opportunity to make this your own!

Discover the charm of this beautifully renovated ranch-style home, set to impress with its major renovations completed in 2026. This home boasts 4 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and comfort. The open layout seamlessly connects the living areas, creating a warm atmosphere perfect for gatherings or quiet evenings at home. The heart of the home features a modern kitchen equipped white cabinets and sleek quartz countertops. Enjoy the convenience of an attached garage 2 car garage with and additional storage. The expansive lot, spanning over 0.61 acres, offers plenty of outdoor space for gardening, play, or simply enjoying the fresh air. This home was designed with a focus on comfort and functionality. Sit on the front porch and enjoy the serene views of the rural farmlands, this property is perfect for those seeking a peaceful retreat while still being close to local shopping and dining. Experience the perfect blend of modern living and timeless charm in this delightful home. Don't miss the opportunity to make this your own!

8760 Black Dog Aly, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

$3,995,000

Located at the end of Market Street in sought-after Oxford, this distinctive waterfront estate on Town Creek combines Victorian elegance, boating amenities, and the convenience of a downtown setting. Designed by Linda Serabian of SOMA Architects, the property offers privacy and expansive creek views just moments from local restaurants, boutique shops, the park, and marinas. The four-bedroom, three-and-a-half-bath main house showcases timeless architecture and thoughtful craftsmanship, with extensive custom millwork, warm wood floors, and four gas fireplaces. A grand tiled foyer with radiant heated floors welcomes you into the home. The well-appointed kitchen and inviting living spaces overlook the pool and Town Creek, while the second-floor deck offers elevated views of the water. Recent improvements include new Marvin windows and French doors, updated HVAC components, fresh interior and exterior paint, and a remodeled full bath. The guest house offers two bedrooms and two full baths, providing a private and versatile extension of the property. Custom millwork, three hidden Murphy beds throughout and a newly updated kitchenette make hosting family and friends effortless. Recent improvements include a new HVAC system, water heater, encapsulated crawl space, and refreshed rear patio. The grounds are equally impressive, with a gunite pool featuring an electric cover, a refreshed poolside patio, and extensive landscaping. Along Town Creek, a well-protected dock accommodates three boats, with water and electric service and mean low water of four feet or greater. A brick driveway, two-car garage with generous shop and storage space, and inviting outdoor gathering areas complete the offering. With its distinctive architecture, separate guest accommodations, dock with three slips, and coveted in-town Oxford location, this is a rare opportunity to experience the best of Eastern Shore waterfront living.

Located at the end of Market Street in sought-after Oxford, this distinctive waterfront estate on Town Creek combines Victorian elegance, boating amenities, and the convenience of a downtown setting. Designed by Linda Serabian of SOMA Architects, the property offers privacy and expansive creek views just moments from local restaurants, boutique shops, the park, and marinas. The four-bedroom, three-and-a-half-bath main house showcases timeless architecture and thoughtful craftsmanship, with extensive custom millwork, warm wood floors, and four gas fireplaces. A grand tiled foyer with radiant heated floors welcomes you into the home. The well-appointed kitchen and inviting living spaces overlook the pool and Town Creek, while the second-floor deck offers elevated views of the water. Recent improvements include new Marvin windows and French doors, updated HVAC components, fresh interior and exterior paint, and a remodeled full bath. The guest house offers two bedrooms and two full baths, providing a private and versatile extension of the property. Custom millwork, three hidden Murphy beds throughout and a newly updated kitchenette make hosting family and friends effortless. Recent improvements include a new HVAC system, water heater, encapsulated crawl space, and refreshed rear patio. The grounds are equally impressive, with a gunite pool featuring an electric cover, a refreshed poolside patio, and extensive landscaping. Along Town Creek, a well-protected dock accommodates three boats, with water and electric service and mean low water of four feet or greater. A brick driveway, two-car garage with generous shop and storage space, and inviting outdoor gathering areas complete the offering. With its distinctive architecture, separate guest accommodations, dock with three slips, and coveted in-town Oxford location, this is a rare opportunity to experience the best of Eastern Shore waterfront living.

307 Market St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

$939,900

Boat-ready waterfront on Tar Creek, with minutes-by-water access to the Tred Avon! Welcome to a turn-key Eastern Shore weekend retreat, quietly tucked at the end of a private lane in the historic village of Bellevue, ideally positioned between St. Michaels and Oxford. This custom 2013 Cape Cod-style home sits gracefully on a tree-framed third of an acre, offering 55 feet of prime shoreline protected by an engineered bulkhead. Designed for water enthusiasts, a private 60-foot pier extends into the creek, complete with an electric lift for jet skis or small tenders, plus dockside power and water. Inside, light-filled living spaces flow across espresso-toned plank floors. Soaring cathedral ceilings, gable windows, and skylights crown the great room, where a stacked-stone gas fireplace anchors the open floor plan. The kitchen features a six-burner gas range, maple Shaker cabinetry, and a center island, adjoining a dining area that easily seats eight or more. Two sets of sliding glass doors open to the backyard deck, leading out to a stone patio, firepit, and outdoor shower. The main level includes two comfortable bedrooms, a full bath, and a laundry room. Upstairs, a skylit loft framed by cherry wood and stainless cable rails overlooks the great room. The vaulted primary suite offers dual closets, barn doors, and an en-suite bath complete with a walk-in tile shower and soapstone trough vanity. Built for low-maintenance, lock-and-leave ownership, the home features a tankless water heater, fire sprinklers, heat pump with central A/C, phone-managed Nest controls, county sewer, and a clean cement crawlspace equipped with a sump pump. Located steps from the Oxford-Bellevue Ferry. About two hours from Washington, D.C., Northern Virginia, Montgomery County, and Wilmington, with Route 301 through Delaware allowing you to bypass Bay Bridge traffic. Leave Friday, be on the water by sunset. Bring your boat!

Boat-ready waterfront on Tar Creek, with minutes-by-water access to the Tred Avon! Welcome to a turn-key Eastern Shore weekend retreat, quietly tucked at the end of a private lane in the historic village of Bellevue, ideally positioned between St. Michaels and Oxford. This custom 2013 Cape Cod-style home sits gracefully on a tree-framed third of an acre, offering 55 feet of prime shoreline protected by an engineered bulkhead. Designed for water enthusiasts, a private 60-foot pier extends into the creek, complete with an electric lift for jet skis or small tenders, plus dockside power and water. Inside, light-filled living spaces flow across espresso-toned plank floors. Soaring cathedral ceilings, gable windows, and skylights crown the great room, where a stacked-stone gas fireplace anchors the open floor plan. The kitchen features a six-burner gas range, maple Shaker cabinetry, and a center island, adjoining a dining area that easily seats eight or more. Two sets of sliding glass doors open to the backyard deck, leading out to a stone patio, firepit, and outdoor shower. The main level includes two comfortable bedrooms, a full bath, and a laundry room. Upstairs, a skylit loft framed by cherry wood and stainless cable rails overlooks the great room. The vaulted primary suite offers dual closets, barn doors, and an en-suite bath complete with a walk-in tile shower and soapstone trough vanity. Built for low-maintenance, lock-and-leave ownership, the home features a tankless water heater, fire sprinklers, heat pump with central A/C, phone-managed Nest controls, county sewer, and a clean cement crawlspace equipped with a sump pump. Located steps from the Oxford-Bellevue Ferry. About two hours from Washington, D.C., Northern Virginia, Montgomery County, and Wilmington, with Route 301 through Delaware allowing you to bypass Bay Bridge traffic. Leave Friday, be on the water by sunset. Bring your boat!

5734 Poplar Ln, Royal Oak

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

$1,595,000

Nestled in the prestigious Canterbury subdivision, this exquisite Cape Cod home offers a harmonious blend of luxury and comfort. Spanning over 4,600 square feet, the interior boasts elegant wood floors and an inviting layout, featuring a spacious kitchen with upgraded countertops and a six-burner stove, perfect for culinary enthusiasts. The dining area and cozy built-ins create an ideal setting for gatherings, while the three fireplaces, adorned with charming mantels, add warmth and sophistication. Retreat to the primary suite, complete with a luxurious bath, or enjoy the convenience of an entry-level bedroom. The thoughtful design includes a laundry chute for effortless living. Outside, the expansive 2.44-acre lot is beautifully landscaped, providing a serene backdrop for relaxation. With an attached two-car garage and a commitment to quality, this home embodies an exclusive lifestyle, inviting you to create cherished memories in a space that truly feels like home.

Nestled in the prestigious Canterbury subdivision, this exquisite Cape Cod home offers a harmonious blend of luxury and comfort. Spanning over 4,600 square feet, the interior boasts elegant wood floors and an inviting layout, featuring a spacious kitchen with upgraded countertops and a six-burner stove, perfect for culinary enthusiasts. The dining area and cozy built-ins create an ideal setting for gatherings, while the three fireplaces, adorned with charming mantels, add warmth and sophistication. Retreat to the primary suite, complete with a luxurious bath, or enjoy the convenience of an entry-level bedroom. The thoughtful design includes a laundry chute for effortless living. Outside, the expansive 2.44-acre lot is beautifully landscaped, providing a serene backdrop for relaxation. With an attached two-car garage and a commitment to quality, this home embodies an exclusive lifestyle, inviting you to create cherished memories in a space that truly feels like home.

6385 Canterbury Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$789,900

Discover the charm of historic Easton with this beautifully designed new construction home, ideally located within walking distance of downtown's wonderful shops, restaurants, and attractions. Thoughtfully designed to blend timeless architectural appeal with modern comfort, this custom-built residence offers the perfect combination of quality, convenience, and style. Featuring a desirable main-level primary suite, a spacious two-car garage, and an inviting backyard, this home is designed for both everyday living and effortless entertaining. Enjoy the benefits of brand-new construction, with beautiful finishes and thoughtful details throughout. Whether you're searching for a full-time residence or a weekend retreat, this exceptional property offers the opportunity to enjoy the best of Eastern Shore living in one of Maryland's most charming historic towns. Completion is anticipated for the first week of November. Don't miss your opportunity to own a beautiful new home in the heart of Easton, where small-town charm meets modern luxury!

Discover the charm of historic Easton with this beautifully designed new construction home, ideally located within walking distance of downtown's wonderful shops, restaurants, and attractions. Thoughtfully designed to blend timeless architectural appeal with modern comfort, this custom-built residence offers the perfect combination of quality, convenience, and style. Featuring a desirable main-level primary suite, a spacious two-car garage, and an inviting backyard, this home is designed for both everyday living and effortless entertaining. Enjoy the benefits of brand-new construction, with beautiful finishes and thoughtful details throughout. Whether you're searching for a full-time residence or a weekend retreat, this exceptional property offers the opportunity to enjoy the best of Eastern Shore living in one of Maryland's most charming historic towns. Completion is anticipated for the first week of November. Don't miss your opportunity to own a beautiful new home in the heart of Easton, where small-town charm meets modern luxury!

422 North St, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$2,495,000

Experience the best of waterfront living on picturesque Trippe Creek, where breathtaking sunsets and sweeping views of the neighboring nature conservancy create an idyllic setting. Nestled in the private Pirates Cove community of Oxford, Maryland, this peaceful retreat offers exceptional privacy, tranquility, and abundant wildlife. Designed for effortless one-level living, this inviting 4-bedroom home features beautiful hardwood and brick flooring, 3 fireplaces (one double sided so feels like 4), and expansive water views. A waterside screened porch provides the perfect setting to relax and enjoy the natural surroundings, while the saltwater pool overlooking the creek offers a wonderful space for outdoor entertaining. Capital improvements to the property 2019 - installed new septic system, enclosed 1-bay of the garage and converted into a finished office/studio. 2020 - installed a new driveway, reset the patio bricks on the back porch. 2021 - completed substantial pool renovation, including both the pool and surround improvements, reset the front walkway/patio brickwork, upgraded the HVAC system. 2023 - new refrigerator. 2024 - new wine refrigerator, constructed a new walkway. 2025 - installed brand new roof, replaced all toilets throughout the home. Through the years of ownership continuously invested in extensive landscaping and site improvements. Boating enthusiasts will appreciate the private pier with approximately 3 feet of mean low water (MLW), providing convenient access to the beautiful waterways of the Eastern Shore. A two-car garage plus a workspace for a studio adds everyday convenience. Offered turnkey with most furnishings included, this exceptional waterfront property also could convey with a 17-foot Scout center console boat with acceptable offer—allowing you to begin enjoying the Eastern Shore lifestyle from day one. Whether you're seeking a full-time residence or a relaxing weekend escape, this special property offers the perfect combination of waterfront recreation, natural beauty, and peaceful coastal living.

Experience the best of waterfront living on picturesque Trippe Creek, where breathtaking sunsets and sweeping views of the neighboring nature conservancy create an idyllic setting. Nestled in the private Pirates Cove community of Oxford, Maryland, this peaceful retreat offers exceptional privacy, tranquility, and abundant wildlife. Designed for effortless one-level living, this inviting 4-bedroom home features beautiful hardwood and brick flooring, 3 fireplaces (one double sided so feels like 4), and expansive water views. A waterside screened porch provides the perfect setting to relax and enjoy the natural surroundings, while the saltwater pool overlooking the creek offers a wonderful space for outdoor entertaining. Capital improvements to the property 2019 - installed new septic system, enclosed 1-bay of the garage and converted into a finished office/studio. 2020 - installed a new driveway, reset the patio bricks on the back porch. 2021 - completed substantial pool renovation, including both the pool and surround improvements, reset the front walkway/patio brickwork, upgraded the HVAC system. 2023 - new refrigerator. 2024 - new wine refrigerator, constructed a new walkway. 2025 - installed brand new roof, replaced all toilets throughout the home. Through the years of ownership continuously invested in extensive landscaping and site improvements. Boating enthusiasts will appreciate the private pier with approximately 3 feet of mean low water (MLW), providing convenient access to the beautiful waterways of the Eastern Shore. A two-car garage plus a workspace for a studio adds everyday convenience. Offered turnkey with most furnishings included, this exceptional waterfront property also could convey with a 17-foot Scout center console boat with acceptable offer—allowing you to begin enjoying the Eastern Shore lifestyle from day one. Whether you're seeking a full-time residence or a relaxing weekend escape, this special property offers the perfect combination of waterfront recreation, natural beauty, and peaceful coastal living.

5718 Pirates Cove Rd, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

$693,900

BE SURE TO WATCH THE VIDEO TOUR TO EXPERIENCE THE PROPERTY AND SETTING. Privacy, a gunite pool, and two acres on Tilghman Island, just 12 miles from St. Michaels. A long, crepe myrtle-lined driveway leads to 4957 Bar Neck Road, surrounded by mature landscaping and expansive lawn with no HOA. The property offers flexibility as a full-time residence, weekend retreat, or potential income-producing short-term rental. Two leaded-glass doors provide separate entrances. The main entrance opens to the foyer, while the second leads to the breezeway and laundry area with a utility sink, storage, and access to a full bath. The main level features hardwood floors, a parlor with built-ins, formal dining room, and family room centered around a wood-burning fireplace. Exposed brick from the fireplace extends upward along the staircase to the second floor, adding warmth and architectural character. Sliding glass doors open directly to the deck, patio, and pool. The kitchen includes granite countertops, stainless steel appliances, light wood cabinetry, and a breakfast bar. Upstairs are three bedrooms, including a spacious primary suite with generous storage and an en-suite bath. A closet-lined passage leads from the bedroom to the bath, which features an oversized jetted tub, double vanity, and abundant natural light. An expansive finished bonus room adds another dimension to the home, with a wood-clad vaulted ceiling, built-in workspace and storage, and a separate mini-split. The space offers tremendous flexibility as an office, den, studio, recreation room, or additional retreat. Outside, the in-ground gunite pool anchors a private outdoor living area surrounded by two acres of open lawn and mature landscaping. A deck, patio, pergola, fire pit, and multiple gathering areas provide plenty of room for relaxing and entertaining. An oversized two-car garage provides additional parking and storage. Improvements include a newer roof, AZEK front decking and steps with vinyl railings, encapsulated crawlspace with concrete floor, tankless water heater, Bosch heating system, and updated primary bath. The home also features two security systems, fire and carbon monoxide detection, and a custom exterior camera system. The property is not located in a flood zone. With two acres, privacy, a gunite pool, generous indoor and outdoor living spaces, and no HOA, 4957 Bar Neck Road offers a distinctive opportunity for year-round living, a second home, or potential short-term rental near St. Michaels and the Chesapeake Bay.

BE SURE TO WATCH THE VIDEO TOUR TO EXPERIENCE THE PROPERTY AND SETTING. Privacy, a gunite pool, and two acres on Tilghman Island, just 12 miles from St. Michaels. A long, crepe myrtle-lined driveway leads to 4957 Bar Neck Road, surrounded by mature landscaping and expansive lawn with no HOA. The property offers flexibility as a full-time residence, weekend retreat, or potential income-producing short-term rental. Two leaded-glass doors provide separate entrances. The main entrance opens to the foyer, while the second leads to the breezeway and laundry area with a utility sink, storage, and access to a full bath. The main level features hardwood floors, a parlor with built-ins, formal dining room, and family room centered around a wood-burning fireplace. Exposed brick from the fireplace extends upward along the staircase to the second floor, adding warmth and architectural character. Sliding glass doors open directly to the deck, patio, and pool. The kitchen includes granite countertops, stainless steel appliances, light wood cabinetry, and a breakfast bar. Upstairs are three bedrooms, including a spacious primary suite with generous storage and an en-suite bath. A closet-lined passage leads from the bedroom to the bath, which features an oversized jetted tub, double vanity, and abundant natural light. An expansive finished bonus room adds another dimension to the home, with a wood-clad vaulted ceiling, built-in workspace and storage, and a separate mini-split. The space offers tremendous flexibility as an office, den, studio, recreation room, or additional retreat. Outside, the in-ground gunite pool anchors a private outdoor living area surrounded by two acres of open lawn and mature landscaping. A deck, patio, pergola, fire pit, and multiple gathering areas provide plenty of room for relaxing and entertaining. An oversized two-car garage provides additional parking and storage. Improvements include a newer roof, AZEK front decking and steps with vinyl railings, encapsulated crawlspace with concrete floor, tankless water heater, Bosch heating system, and updated primary bath. The home also features two security systems, fire and carbon monoxide detection, and a custom exterior camera system. The property is not located in a flood zone. With two acres, privacy, a gunite pool, generous indoor and outdoor living spaces, and no HOA, 4957 Bar Neck Road offers a distinctive opportunity for year-round living, a second home, or potential short-term rental near St. Michaels and the Chesapeake Bay.

4957 Bar Neck Rd, Tilghman

Listing courtesy of Compass. Contact:

$520,000

Chesapeake by Del Webb. This one owner Merion model is sited on an end lot overlooking a pond and community open space. Living room/office, family room with gas fireplace and wood flooring, formal dining room, kitchen with breakfast area, stainless appliances and granite countertops. 1st floor primary bedroom with trey ceiling and walk-in closet, primary bath with walk-in shower, soaking tub and double vanities, powder room and main floor laundry. 2nd floor features a loft and 2 guest bedrooms and bath. Large attached front loading garage with walk-up storage, lawn irrigation, patio with awning and beautiful landscaping. Prime lot on quiet street. Community amenities: Clubhouse with library, billiards room, meeting room, exercise rooms and game room plus outdoor pool and picnic areas, tennis/pickleball courts, bocce ball and exercise paths. 55+ age-restricted section. Close to downtown Easton, medical facilities, shopping, churches and restaurants.

Chesapeake by Del Webb. This one owner Merion model is sited on an end lot overlooking a pond and community open space. Living room/office, family room with gas fireplace and wood flooring, formal dining room, kitchen with breakfast area, stainless appliances and granite countertops. 1st floor primary bedroom with trey ceiling and walk-in closet, primary bath with walk-in shower, soaking tub and double vanities, powder room and main floor laundry. 2nd floor features a loft and 2 guest bedrooms and bath. Large attached front loading garage with walk-up storage, lawn irrigation, patio with awning and beautiful landscaping. Prime lot on quiet street. Community amenities: Clubhouse with library, billiards room, meeting room, exercise rooms and game room plus outdoor pool and picnic areas, tennis/pickleball courts, bocce ball and exercise paths. 55+ age-restricted section. Close to downtown Easton, medical facilities, shopping, churches and restaurants.

7196 Bobs Way, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$478,940

New main‑level primary bedroom home is about to start construction for a spring move‑in! This thoughtfully designed home offers 4 bedrooms and 3.5 bathrooms and is located in amenity filled, Lakeside at Trappe! The open main level features volume ceilings in the great room, creating an airy and inviting living space. Gourmet kitchen with stainless steel appliances including hood. The main‑level primary suite is a true retreat, complete with a deluxe bath including a separate soaking tub and shower. Located in Lakeside at Trappe, an amenity‑rich, master‑planned community just minutes from Easton, residents enjoy a lifestyle designed for connection and recreation including Resort‑style swimming pool, Bathhouse with fitness room, Ping pong & cornhole, Playground & sports courts, Dedicated Bark Park plus an immersive lakeside experience is planned, offering even more opportunities to enjoy the outdoors and waterfront lifestyle. With easy access to Easton, Cambridge, and surrounding areas, Lakeside at Trappe combines small‑town charm with everyday convenience in the heart of the growing Chesapeake Bay region. Please note that the photos are of a model as this home has not yet finished construction, and the photos may show additional options that are not included. ✨ Ask about builder incentives!

New main‑level primary bedroom home is about to start construction for a spring move‑in! This thoughtfully designed home offers 4 bedrooms and 3.5 bathrooms and is located in amenity filled, Lakeside at Trappe! The open main level features volume ceilings in the great room, creating an airy and inviting living space. Gourmet kitchen with stainless steel appliances including hood. The main‑level primary suite is a true retreat, complete with a deluxe bath including a separate soaking tub and shower. Located in Lakeside at Trappe, an amenity‑rich, master‑planned community just minutes from Easton, residents enjoy a lifestyle designed for connection and recreation including Resort‑style swimming pool, Bathhouse with fitness room, Ping pong & cornhole, Playground & sports courts, Dedicated Bark Park plus an immersive lakeside experience is planned, offering even more opportunities to enjoy the outdoors and waterfront lifestyle. With easy access to Easton, Cambridge, and surrounding areas, Lakeside at Trappe combines small‑town charm with everyday convenience in the heart of the growing Chesapeake Bay region. Please note that the photos are of a model as this home has not yet finished construction, and the photos may show additional options that are not included. ✨ Ask about builder incentives!

285 Silver Lake Ln, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

$389,999

Beautifully maintained and thoughtfully updated, this move-in-ready home offers a comfortable layout with LVP flooring, plantation shutters, and an inviting kitchen featuring quartz countertops, stainless steel appliances, a large island, and a breakfast area. The spacious living room offers plenty of room for a separate dining area. Upstairs, the primary suite features a full bath and two large walk-in closets, along with two additional bedrooms and a full bath. The finished lower level adds a family room, a separate office/bonus room with French doors, a powder room, and a laundry room with washer and dryer. Outside, enjoy a rear patio overlooking the private backyard, a paved driveway, and a storage shed that conveys as-is. Roof replaced October 2019, A/C 2018, Water heater 2013. Recently replace flooring with LVP, carpet replaced, kitchen cabinets painted and new hardware Oct 2026 . All bathrooms recently renovated. Located in a popular neighborhood close to downtown Easton and its many amenities! Don't miss this move in ready home.

Beautifully maintained and thoughtfully updated, this move-in-ready home offers a comfortable layout with LVP flooring, plantation shutters, and an inviting kitchen featuring quartz countertops, stainless steel appliances, a large island, and a breakfast area. The spacious living room offers plenty of room for a separate dining area. Upstairs, the primary suite features a full bath and two large walk-in closets, along with two additional bedrooms and a full bath. The finished lower level adds a family room, a separate office/bonus room with French doors, a powder room, and a laundry room with washer and dryer. Outside, enjoy a rear patio overlooking the private backyard, a paved driveway, and a storage shed that conveys as-is. Roof replaced October 2019, A/C 2018, Water heater 2013. Recently replace flooring with LVP, carpet replaced, kitchen cabinets painted and new hardware Oct 2026 . All bathrooms recently renovated. Located in a popular neighborhood close to downtown Easton and its many amenities! Don't miss this move in ready home.

29214 Corbin Pkwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$479,000

This 4-bedroom, 2.5-bath home offers a bright, open floor plan, well-designed living spaces, and a great location close to downtown Easton. Situated on a corner lot, the property features a beautifully landscaped backyard, Trex deck and storage shed. The main level includes formal living and dining rooms, an eat-in kitchen with abundant cabinetry, a custom center island with breakfast bar, stainless steel appliances, and butler’s pantry. A side-entry, attached two-car garage connects to a spacious mudroom. Upstairs, the large primary suite features a three walk-in closets and remodeled en-suite bath with a custom-tiled shower, along with three additional bedrooms and a full bath. Concrete crawl space. Enjoy direct access to the Rails to Trails, plus convenient access to a public boat ramp, community pool, and parks. The HOA includes common area maintenance and snow removal. Located just minutes from downtown Easton’s shopping, dining, YMCA, and local amenities, this home offers the space you need and the lifestyle that makes the Eastern Shore special.

This 4-bedroom, 2.5-bath home offers a bright, open floor plan, well-designed living spaces, and a great location close to downtown Easton. Situated on a corner lot, the property features a beautifully landscaped backyard, Trex deck and storage shed. The main level includes formal living and dining rooms, an eat-in kitchen with abundant cabinetry, a custom center island with breakfast bar, stainless steel appliances, and butler’s pantry. A side-entry, attached two-car garage connects to a spacious mudroom. Upstairs, the large primary suite features a three walk-in closets and remodeled en-suite bath with a custom-tiled shower, along with three additional bedrooms and a full bath. Concrete crawl space. Enjoy direct access to the Rails to Trails, plus convenient access to a public boat ramp, community pool, and parks. The HOA includes common area maintenance and snow removal. Located just minutes from downtown Easton’s shopping, dining, YMCA, and local amenities, this home offers the space you need and the lifestyle that makes the Eastern Shore special.

201 Coleman Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$325,000

Welcome to the most charming historic colonial to hit the Eastern Shore during this fall market! Priced to sell, this stunning single family residence offers tons of natural light, new flooring throughout, fresh paint, a clean kitchen aesthetic and a spa like bathroom on the second level. The backyard extends for plenty of parking space, gardening opportunities, space to host or build a fire pit and more! The owners put love into this house to make sure its new family can really enjoy going into the holidays with real peace of mind. Make sure to schedule your private showing with the listing agent today!

4 Beds ⋅ 2 Baths

Welcome to the most charming historic colonial to hit the Eastern Shore during this fall market! Priced to sell, this stunning single family residence offers tons of natural light, new flooring throughout, fresh paint, a clean kitchen aesthetic and a spa like bathroom on the second level. The backyard extends for plenty of parking space, gardening opportunities, space to host or build a fire pit and more! The owners put love into this house to make sure its new family can really enjoy going into the holidays with real peace of mind. Make sure to schedule your private showing with the listing agent today!

619 Goldsborough St, Easton

Listing courtesy of Next Step Realty. Contact:

$5,750,000

Pine Point Farm is a remarkable 77+ acre waterfront estate on the scenic shores of Broad Creek comprising 4 total bedrooms, 4 full baths, and two half baths, and offering an exceptional combination of privacy, natural beauty, waterfront amenities, and newly constructed improvements. Built in 2023, the coastal-style main residence features an inviting open-concept kitchen, dining, and family room with beamed, vaulted ceilings and a wood-burning fireplace. Multiple sliders and doors open to the spacious rear deck and a screened-in porch, creating a seamless connection between the interior and the surrounding landscape while taking full advantage of the water views. The main house includes two en-suite bedrooms, an office/den, and a powder room, along with hardwood flooring throughout, and numerous built-ins. Also completed in 2023, the guest house and attached two-car garage are connected to the main residence by a breezeway. The guest house offers a large living room, kitchenette, and full bath on the main level, with two spacious bedrooms and a large hall bath upstairs. This thoughtfully designed space is ideal for guests, extended family, or a private retreat. The outdoor amenities are equally impressive. A large, stocked pond is home to hybrid bass, largemouth bass, and bluegill, offering a private setting for fishing and recreation. Along Broad Creek, the substantial dock features water and electric, approximately 3.5 feet mean low water, a boat lift, and multiple slips, providing excellent access for boating and waterfront activities. Additional improvements include a large block outbuilding ideal for equipment, storage, hobbies, or workshop use; an in-ground pool; irrigation system; and two generators. The sale includes a separate 0.146-acre waterfront lot on Harris Creek, and two additional, platted waterfront lots, providing more possibilities for the new owner. (Please note there is potentially an Eagles' Nest on the property). Pine Point Farm is a truly exceptional waterfront estate, combining 77+ acres, two newly constructed residences, extensive waterfront amenities, recreational features, and remarkable privacy—all in one extraordinary offering.

2 Beds ⋅ 3 Baths

Pine Point Farm is a remarkable 77+ acre waterfront estate on the scenic shores of Broad Creek comprising 4 total bedrooms, 4 full baths, and two half baths, and offering an exceptional combination of privacy, natural beauty, waterfront amenities, and newly constructed improvements. Built in 2023, the coastal-style main residence features an inviting open-concept kitchen, dining, and family room with beamed, vaulted ceilings and a wood-burning fireplace. Multiple sliders and doors open to the spacious rear deck and a screened-in porch, creating a seamless connection between the interior and the surrounding landscape while taking full advantage of the water views. The main house includes two en-suite bedrooms, an office/den, and a powder room, along with hardwood flooring throughout, and numerous built-ins. Also completed in 2023, the guest house and attached two-car garage are connected to the main residence by a breezeway. The guest house offers a large living room, kitchenette, and full bath on the main level, with two spacious bedrooms and a large hall bath upstairs. This thoughtfully designed space is ideal for guests, extended family, or a private retreat. The outdoor amenities are equally impressive. A large, stocked pond is home to hybrid bass, largemouth bass, and bluegill, offering a private setting for fishing and recreation. Along Broad Creek, the substantial dock features water and electric, approximately 3.5 feet mean low water, a boat lift, and multiple slips, providing excellent access for boating and waterfront activities. Additional improvements include a large block outbuilding ideal for equipment, storage, hobbies, or workshop use; an in-ground pool; irrigation system; and two generators. The sale includes a separate 0.146-acre waterfront lot on Harris Creek, and two additional, platted waterfront lots, providing more possibilities for the new owner. (Please note there is potentially an Eagles' Nest on the property). Pine Point Farm is a truly exceptional waterfront estate, combining 77+ acres, two newly constructed residences, extensive waterfront amenities, recreational features, and remarkable privacy—all in one extraordinary offering.

23505 Pine Point Rd, Bozman

Listing courtesy of Meredith Fine Properties. Contact:

$465,000

NEW HOME FEELING WITHOUT THE WAIT! Why wait for new construction when you can move right into this nearly new home, less than two years young! Enjoy a beautiful open floor plan, stylish stone countertops, a spacious kitchen island, and plenty of room to spread out. The fourth bedroom makes an ideal home office, guest room, or flex space to fit your lifestyle. Park in your finished garage and keep your car safe from the snow this winter! Step outside to a nice, level backyard with room to entertain, celebrate special occasions, enjoy outdoor activities, or simply relax. Skip the construction delays and make this beautiful home yours! Don't miss your opportunity to enjoy the benefits of a nearly new home without the wait.

4 Beds ⋅ 2 Baths

NEW HOME FEELING WITHOUT THE WAIT! Why wait for new construction when you can move right into this nearly new home, less than two years young! Enjoy a beautiful open floor plan, stylish stone countertops, a spacious kitchen island, and plenty of room to spread out. The fourth bedroom makes an ideal home office, guest room, or flex space to fit your lifestyle. Park in your finished garage and keep your car safe from the snow this winter! Step outside to a nice, level backyard with room to entertain, celebrate special occasions, enjoy outdoor activities, or simply relax. Skip the construction delays and make this beautiful home yours! Don't miss your opportunity to enjoy the benefits of a nearly new home without the wait.

31336 Dukes Bridge Rd, Cordova

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

$799,000

Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe. Time to make your personal selections. Make this home your personal statement. Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more. Make this your dream home.