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This private in-town cottage is located in the heart of Saint Michaels , a 5 minute walk from the town’s renowned boutiques, acclaimed restaurants, waterfront parks along the Miles River, the community pool, and the YMCA. Thoughtfully reimagined from the studs out including new HVAC, Plumbing, Electrical and Roof Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled interior featuring soaring vaulted ceilings and an open-concept floor plan designed for effortless everyday living. A beautifully appointed chef’s kitchen is complemented by three well-proportioned bedrooms and two elegantly finished full baths—all conveniently situated on a single level. Outside, professionally designed landscaping surrounds a private backyard and patio creating a tranquil setting for outdoor dining, entertaining, or quiet relaxation. Offering the rare combination of a turnkey renovation and one of Maryland’s most desirable small-town settings, 803 New Lane presents an exceptional opportunity to enjoy Eastern Shore living at its finest.

803 New Ln, St Michaels

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

$549,000

Enjoy the best of Eastern Shore living in the desirable waterfront community of Tilghman on the Chesapeake! Originally designed as the model home, this beautifully one-level residence offers 3 bedrooms, 2.5 baths an open-concept floor plan and numerous upgrades throughout. Designed to maximize space and natural light, the home features 9-foot ceilings, recessed lighting, expansive windows and luxury vinyl plank flooring that flows seamlessly throughout the main living areas. The kitchen features granite countertops, ample cabinetry, tile backsplash, stainless steel appliances, a center island with raised breakfast bar and a pantry closet. The adjoining dining area overlooks the backyard and picturesque pond. The spacious living room features a beautiful double-sided fireplace shared with the screened porch, bringing warmth and ambiance to both spaces. The thoughtfully designed split-bedroom floor plan offers privacy for the primary suite, complete with a walk-in closet and an ensuite bath featuring a granite double-sink vanity and tile and glass shower. Two additional bedrooms and a full guest bath are conveniently located on the opposite side of the home, while a powder room provides added convenience for guests. Step outside to the screened porch and enjoy peaceful views of the backyard and beautiful pond with its fountain perfect, for enjoying your morning coffee or unwinding by the fireplace in the evening, this inviting outdoor retreat is sure to become a favorite spot. Additional features include a large laundry room, two-car garage and a fully conditioned crawlspace. Residents of Tilghman on the Chesapeake enjoy access to the waterfront clubhouse, featuring a swimming pool, recreation room and expansive balcony ideal for gatherings and entertaining. Boat slips are also available for an additional fee, providing convenient access to the Chesapeake Bay and its scenic tributaries, renowned for fishing and boating. Ideally situated near local restaurants, marinas and boat landings, the community offers an excellent launching point for exploring St. Michaels, Kent Island, Oxford, Cambridge and Annapolis by boat.

Enjoy the best of Eastern Shore living in the desirable waterfront community of Tilghman on the Chesapeake! Originally designed as the model home, this beautifully one-level residence offers 3 bedrooms, 2.5 baths an open-concept floor plan and numerous upgrades throughout. Designed to maximize space and natural light, the home features 9-foot ceilings, recessed lighting, expansive windows and luxury vinyl plank flooring that flows seamlessly throughout the main living areas. The kitchen features granite countertops, ample cabinetry, tile backsplash, stainless steel appliances, a center island with raised breakfast bar and a pantry closet. The adjoining dining area overlooks the backyard and picturesque pond. The spacious living room features a beautiful double-sided fireplace shared with the screened porch, bringing warmth and ambiance to both spaces. The thoughtfully designed split-bedroom floor plan offers privacy for the primary suite, complete with a walk-in closet and an ensuite bath featuring a granite double-sink vanity and tile and glass shower. Two additional bedrooms and a full guest bath are conveniently located on the opposite side of the home, while a powder room provides added convenience for guests. Step outside to the screened porch and enjoy peaceful views of the backyard and beautiful pond with its fountain perfect, for enjoying your morning coffee or unwinding by the fireplace in the evening, this inviting outdoor retreat is sure to become a favorite spot. Additional features include a large laundry room, two-car garage and a fully conditioned crawlspace. Residents of Tilghman on the Chesapeake enjoy access to the waterfront clubhouse, featuring a swimming pool, recreation room and expansive balcony ideal for gatherings and entertaining. Boat slips are also available for an additional fee, providing convenient access to the Chesapeake Bay and its scenic tributaries, renowned for fishing and boating. Ideally situated near local restaurants, marinas and boat landings, the community offers an excellent launching point for exploring St. Michaels, Kent Island, Oxford, Cambridge and Annapolis by boat.

5657 Trafalgar Cir, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

$149,900

A Little Charm, A Lot of Possibilities! Just $149,900!! Looking for an affordable place to call home or a great investment opportunity? This charming home in Cordova offers plenty of possibilities! Features 2 bedrooms and 2 full baths, including a desirable first-floor primary bedroom & full bath, a second upper bedroom with an extra room being used currently as a closet and storage but could be used as a 3rd bedroom, office or den. Also, a welcoming living room, and a spacious eat-in Country Kitchen with updated cabinets, flooring, countertops and more. This home is ready for its next owner to move in and enjoy. Situated on .34 acres and the convenience of being just minutes from Easton. Whether you are a first time home buyer, looking to downsize, or searching for an investment property, this little gem deserves your attention. Don't miss an opportunity to make it yours.

A Little Charm, A Lot of Possibilities! Just $149,900!! Looking for an affordable place to call home or a great investment opportunity? This charming home in Cordova offers plenty of possibilities! Features 2 bedrooms and 2 full baths, including a desirable first-floor primary bedroom & full bath, a second upper bedroom with an extra room being used currently as a closet and storage but could be used as a 3rd bedroom, office or den. Also, a welcoming living room, and a spacious eat-in Country Kitchen with updated cabinets, flooring, countertops and more. This home is ready for its next owner to move in and enjoy. Situated on .34 acres and the convenience of being just minutes from Easton. Whether you are a first time home buyer, looking to downsize, or searching for an investment property, this little gem deserves your attention. Don't miss an opportunity to make it yours.

11443 Kittys Corner Rd, Cordova

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

$235,000

Located in the desirable historic waterfront town of St. Michaels, this 5,520-square-foot in-town lot places you around the corner from downtown shops, restaurants, and museums. Enjoy close proximity to the local destinations that make St. Michaels a sought-after Eastern Shore community. An excellent opportunity for renovation or new construction in the heart of downtown St. Michaels, subject to applicable zoning, permits, and approvals. An existing house is located on the property. No one is permitted to enter the house. Buyer to independently verify property condition, square footage, permits, zoning, and suitability for intended use.

105 W Marengo St, 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, every corner of this home exudes warmth and sophistication. 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:

$599,000

Coming soon! Charming home. Beautiful Community. Coastal Eastern Shore Living! Get ready to fall in love with this inviting 4-bedroom home nestled in the popular Oxford Community! This home offers the perfect blend of traditional charm, comfortable living and wonderful spaces for entertaining family and friends! Ready for your personal touches! This 4 bedroom, 1 1/2 bath has an attached 1 car garage with a relaxing backyard with deck-ideal for morning coffee, outdoor dining or unwinding after a long day. Located along Maryland's beautiful Eastern Shore, Oxford is a picturesque waterfront town known for its rich history, scenic waterways, charming streets and relaxed coastal lifestyle. Enjoy local restaurants, boating, just a few blocks from waterfront views and the small-town atmosphere make Oxford such a special place to call home.

4 Beds ⋅ 2 Baths

Coming soon! Charming home. Beautiful Community. Coastal Eastern Shore Living! Get ready to fall in love with this inviting 4-bedroom home nestled in the popular Oxford Community! This home offers the perfect blend of traditional charm, comfortable living and wonderful spaces for entertaining family and friends! Ready for your personal touches! This 4 bedroom, 1 1/2 bath has an attached 1 car garage with a relaxing backyard with deck-ideal for morning coffee, outdoor dining or unwinding after a long day. Located along Maryland's beautiful Eastern Shore, Oxford is a picturesque waterfront town known for its rich history, scenic waterways, charming streets and relaxed coastal lifestyle. Enjoy local restaurants, boating, just a few blocks from waterfront views and the small-town atmosphere make Oxford such a special place to call home.

301 Oxford Rd, Oxford

Listing courtesy of Coldwell Banker Realty. Contact:

$249,900

Nestled in the charming downtown of St Michaels, this well-maintained 2 bedroom, 1 bathroom townhouse offers a perfect blend of comfort and convenience. This traditional-style home features an interior with luxury vinyl plank downstairs, cozy carpet flooring upstairs, ceiling fans and a kitchen equipped with modern appliances including a built-in microwave, dishwasher, and electric oven/range, making meal preparation a breeze. Enjoy the convenience of a stacked washer and dryer, along with a tankless instant water heater. Step outside to a cleared rear yard with a privacy fence, perfect for outdoor gatherings. With no thru street, this property offers a peaceful retreat while still being close to the vibrant downtown area. St Michaels is not just a place to live; it's a community that thrives on connection hosting events throughout the year. Residents enjoy the local restaurants, stores, parks, birding trails, boating and waterfront sunsets within walking distance making it an ideal place to call home. Must be owner occupied, no rentals allowed. Schedule your showing today!

2 Beds ⋅ 1 Baths

Nestled in the charming downtown of St Michaels, this well-maintained 2 bedroom, 1 bathroom townhouse offers a perfect blend of comfort and convenience. This traditional-style home features an interior with luxury vinyl plank downstairs, cozy carpet flooring upstairs, ceiling fans and a kitchen equipped with modern appliances including a built-in microwave, dishwasher, and electric oven/range, making meal preparation a breeze. Enjoy the convenience of a stacked washer and dryer, along with a tankless instant water heater. Step outside to a cleared rear yard with a privacy fence, perfect for outdoor gatherings. With no thru street, this property offers a peaceful retreat while still being close to the vibrant downtown area. St Michaels is not just a place to live; it's a community that thrives on connection hosting events throughout the year. Residents enjoy the local restaurants, stores, parks, birding trails, boating and waterfront sunsets within walking distance making it an ideal place to call home. Must be owner occupied, no rentals allowed. Schedule your showing today!

219 Webb Ln, Saint Michaels

Listing courtesy of Coldwell Banker Realty. Contact:

$975,000

5 Beds ⋅ 4 Baths

27330 Rest Cir, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$518,000

The Woods at Stoney Ridge - Original owners. Dutchman model in excellent turn-key condition. The owners have meticulously maintained this 3,546+ SF home. It is substantially larger than most in the community. Immediate occupancy. *The tax records do not reflect the finished 3rd floor with a bedroom/fitness/storage room, living/media room, and ensuite bathroom. This is the only home in the community with a finished 3rd floor living space, more square footage. Ideal floor plan for multi-generational living. 5 total bedrooms, 3-1/2 baths, 2 story great room with 17' vaulted ceiling, formal living room, formal dining, office/library (this is one room with mult-usage). Spacious Primary with ensuite bathroom > double vanity, Jacuzzi tub, and water closet. Gas cooking, gas & electric heat, gas fireplace, tankless water heater. Full laundry room off the kitchen. Deck access off the breakfast/kitchen/great room areas. Flooring is a blend of hardwood, tile, and carpet. Bright natural light in all rooms. ACU-RITE Humidity Monitor in the crawlspace with a monitor in the home (see photo). Rear storage shed for lawn equipment. The back area of the lot is wooded, all other areas of the property have mature landscaping. All window treatments, mirror and sconces over the fireplace, and extra garage refrigerator convey. The Woods at Stoney Ridge is conveniently located near the RT 50 corridor, close to schools, medical, shopping, and eateries.

5 Beds ⋅ 4 Baths

The Woods at Stoney Ridge - Original owners. Dutchman model in excellent turn-key condition. The owners have meticulously maintained this 3,546+ SF home. It is substantially larger than most in the community. Immediate occupancy. *The tax records do not reflect the finished 3rd floor with a bedroom/fitness/storage room, living/media room, and ensuite bathroom. This is the only home in the community with a finished 3rd floor living space, more square footage. Ideal floor plan for multi-generational living. 5 total bedrooms, 3-1/2 baths, 2 story great room with 17' vaulted ceiling, formal living room, formal dining, office/library (this is one room with mult-usage). Spacious Primary with ensuite bathroom > double vanity, Jacuzzi tub, and water closet. Gas cooking, gas & electric heat, gas fireplace, tankless water heater. Full laundry room off the kitchen. Deck access off the breakfast/kitchen/great room areas. Flooring is a blend of hardwood, tile, and carpet. Bright natural light in all rooms. ACU-RITE Humidity Monitor in the crawlspace with a monitor in the home (see photo). Rear storage shed for lawn equipment. The back area of the lot is wooded, all other areas of the property have mature landscaping. All window treatments, mirror and sconces over the fireplace, and extra garage refrigerator convey. The Woods at Stoney Ridge is conveniently located near the RT 50 corridor, close to schools, medical, shopping, and eateries.

7084 Redwood Ct, Easton

Listing courtesy of Newport Bay Realty. Contact:

$650,000

Discover an exceptional opportunity to build your dream home in the sought-after community of Llandaff at Cooke's Hope. Beautifully elevated and overlooking picturesque Peachblossom Creek, this perc-approved waterfront lot offers a peaceful, private setting surrounded by the natural beauty of Maryland's Eastern Shore. Mature trees along the property boundaries enhance the sense of privacy, while scenic creek views and abundant wildlife create a tranquil backdrop. Enjoy opportunities for kayaking, canoeing, and exploring the surrounding waterways. The potential for a private pier offers additional possibilities for enjoying life by the water, subject to buyer verification and applicable HOA approvals. Conveniently located near the charming towns of Easton and Oxford, Llandaff offers a wonderful balance of natural beauty, privacy, and accessibility. The well-established community features common area maintenance and roadside mowing to the split rail fencing, included in the current annual HOA fee of $600. An inviting setting to create a custom waterfront retreat and embrace relaxed Eastern Shore living.

28752 Jennings Rd Unit LOT 4, Easton

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

$650,000

Discover an exceptional opportunity to build your dream home in the sought-after community of Llandaff at Cooke's Hope. Beautifully elevated and overlooking picturesque Peachblossom Creek, this perc-approved waterfront lot offers a peaceful, private setting surrounded by the natural beauty of Maryland's Eastern Shore. Mature trees along the property boundaries enhance the sense of privacy, while scenic creek views and abundant wildlife create a tranquil backdrop. Enjoy opportunities for kayaking, canoeing, and exploring the surrounding waterways. The potential for a private pier offers additional possibilities for enjoying life by the water, subject to buyer verification and applicable HOA approvals. Conveniently located near the charming towns of Easton and Oxford, Llandaff offers a wonderful balance of natural beauty, privacy, and accessibility. The well-established community features common area maintenance and roadside mowing to the split rail fencing, included in the current annual HOA fee of $600. An inviting setting to create a custom waterfront retreat and embrace relaxed Eastern Shore living.

28776 Jennings Rd Unit LOT 5, Easton

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

$995,000

Nestled in the Easton Club along the shores of the Tred Avon river, this exquisite Craftsman-style residence offers a harmonious blend of luxury and comfort. Spanning over 3,900 square feet, this home features four spacious bedrooms and 3 full and 2 half bath that are elegantly appointed, including a primary suite with a waterside view, his and her private baths and dressing rooms.. Step inside to discover an inviting open floor plan adorned with rich hardwood floors, ceramic tile, and plush carpeting. The gourmet kitchen is a chef's dream, equipped with stainless steel Wolf gas cooktop and oven, a large island, a butlers pantry, granite counters and an eat in waterside dining nook. Enjoy cozy evenings by the gas fireplace in the living room, enhanced by bookshelves and charming wainscoting. The exterior is equally impressive, featuring extensive hardscaping, lush landscaping, and a private dock site on the Tred Avon River. Embrace outdoor living with a community pool, tennis courts, and a BBQ grill for summer gatherings. The home also boasts an immaculate three-car garage with electric vehicle charging capabilities and ample off-street parking. With water features that include a serene waterfall and a tranquil atmosphere, this home is a sanctuary for those seeking an exclusive lifestyle. Experience the perfect blend of elegance and comfort in this remarkable property.

4 Beds ⋅ 5 Baths

Nestled in the Easton Club along the shores of the Tred Avon river, this exquisite Craftsman-style residence offers a harmonious blend of luxury and comfort. Spanning over 3,900 square feet, this home features four spacious bedrooms and 3 full and 2 half bath that are elegantly appointed, including a primary suite with a waterside view, his and her private baths and dressing rooms.. Step inside to discover an inviting open floor plan adorned with rich hardwood floors, ceramic tile, and plush carpeting. The gourmet kitchen is a chef's dream, equipped with stainless steel Wolf gas cooktop and oven, a large island, a butlers pantry, granite counters and an eat in waterside dining nook. Enjoy cozy evenings by the gas fireplace in the living room, enhanced by bookshelves and charming wainscoting. The exterior is equally impressive, featuring extensive hardscaping, lush landscaping, and a private dock site on the Tred Avon River. Embrace outdoor living with a community pool, tennis courts, and a BBQ grill for summer gatherings. The home also boasts an immaculate three-car garage with electric vehicle charging capabilities and ample off-street parking. With water features that include a serene waterfall and a tranquil atmosphere, this home is a sanctuary for those seeking an exclusive lifestyle. Experience the perfect blend of elegance and comfort in this remarkable property.

28598 9th Dr, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

$525,000

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)

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 property boasts its own private, boutique winery, adding a layer of refined luxury to the expansive grounds. 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 property boasts its own private, boutique winery, adding a layer of refined luxury to the expansive grounds. 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

4 Beds ⋅ 3 Baths

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:

$27,000

Ocean Gtwy, Trappe

Listing courtesy of Meredith Fine Properties. 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 Cove 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 Cove 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:

$135,000

One story manufactured mobile home, located in a thriving and active Hyde Park, a 55+ Community With a 8 x 10 shed, handicap ramp, three-season room to relax. Hyde Park amenities include walking trails, dog park, shuffle board and picnic areas, pool, workout room, boat & Rv storage. Buyers must be approved by Hyde Park before any offer.

One story manufactured mobile home, located in a thriving and active Hyde Park, a 55+ Community With a 8 x 10 shed, handicap ramp, three-season room to relax. Hyde Park amenities include walking trails, dog park, shuffle board and picnic areas, pool, workout room, boat & Rv storage. Buyers must be approved by Hyde Park before any offer.

17 Downing St, Easton

Listing courtesy of Benson & Mangold, LLC. 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!

4 Beds ⋅ 3 Baths

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.

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:

$445,000

Elegant two-bedroom, two bath Shireton Condominium Unit with ten-foot ceilings, new HVAC and hot water tank. Centrally located in Easton's downtown Historic District - in close proximity to shopping, galleries, dining, theater and parks. Four floor building, secure underground parking, 2 elevators, built with block, brick, poured concrete and steel. Approximately 30 units in building. The main entrance features a grand common meeting room, private post office for residents and a private meeting room.

Elegant two-bedroom, two bath Shireton Condominium Unit with ten-foot ceilings, new HVAC and hot water tank. Centrally located in Easton's downtown Historic District - in close proximity to shopping, galleries, dining, theater and parks. Four floor building, secure underground parking, 2 elevators, built with block, brick, poured concrete and steel. Approximately 30 units in building. The main entrance features a grand common meeting room, private post office for residents and a private meeting room.

117 E Dover St E Unit 207, Easton

Listing courtesy of Benson & Mangold, LLC. 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.