Mdresidentialrealty.com Search Results

*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* NOTE: Has public sewer and well. Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**

20 Beds ⋅ 24 Baths

*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* NOTE: Has public sewer and well. Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**

21384 Coopertown Rd, Tilghman

Listing courtesy of Compass. Contact:

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

$3,900,000

*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**

21384 Coopertown Rd, Tilghman

Listing courtesy of Compass. Contact:

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

$1,790,000

Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat on Tilghman Island. Thoughtfully redesigned and updated in 2023, this exceptional property seamlessly blends refined coastal living with the tranquility and natural beauty of its extraordinary waterfront setting. Offered fully furnished, the home provides a truly turnkey opportunity, allowing the next owner to immediately enjoy the Chesapeake Bay lifestyle. Inside, the light-filled great room is the heart of the home, with soaring vaulted ceilings, a gas fireplace, dramatic floor-to-ceiling windows that capture breathtaking panoramic water views, and stunning sunsets. Every detail of the renovation was carefully considered to enhance both comfort and connection to the outdoors, including the addition of a screened porch with vaulted ceilings and its own fireplace, an ideal space for year-round waterfront entertaining and relaxation. The first-floor primary suite offers a private sanctuary overlooking the Bay, complete with expansive water views, a spacious en suite bath, and generous walk-in closets. Designed for effortless indoor-outdoor living, the home also features low-maintenance composite decking, multiple waterfront gathering spaces, and a heated gunite pool perfectly positioned to enjoy the surrounding scenery. For boating enthusiasts, the property is equally exceptional. A private dock equipped with a boat lift and jet ski lift provides immediate access to some of the Eastern Shore’s finest boating, fishing, and waterfront destinations. The protected rip-rapped shoreline adds both beauty and peace of mind. This is a rare opportunity to own a fully furnished, turnkey waterfront escape offering luxury, privacy, and unforgettable Chesapeake Bay sunsets, all within the laid-back charm and timeless appeal that make Tilghman Island so special.

5 Beds ⋅ 4 Baths

Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat on Tilghman Island. Thoughtfully redesigned and updated in 2023, this exceptional property seamlessly blends refined coastal living with the tranquility and natural beauty of its extraordinary waterfront setting. Offered fully furnished, the home provides a truly turnkey opportunity, allowing the next owner to immediately enjoy the Chesapeake Bay lifestyle. Inside, the light-filled great room is the heart of the home, with soaring vaulted ceilings, a gas fireplace, dramatic floor-to-ceiling windows that capture breathtaking panoramic water views, and stunning sunsets. Every detail of the renovation was carefully considered to enhance both comfort and connection to the outdoors, including the addition of a screened porch with vaulted ceilings and its own fireplace, an ideal space for year-round waterfront entertaining and relaxation. The first-floor primary suite offers a private sanctuary overlooking the Bay, complete with expansive water views, a spacious en suite bath, and generous walk-in closets. Designed for effortless indoor-outdoor living, the home also features low-maintenance composite decking, multiple waterfront gathering spaces, and a heated gunite pool perfectly positioned to enjoy the surrounding scenery. For boating enthusiasts, the property is equally exceptional. A private dock equipped with a boat lift and jet ski lift provides immediate access to some of the Eastern Shore’s finest boating, fishing, and waterfront destinations. The protected rip-rapped shoreline adds both beauty and peace of mind. This is a rare opportunity to own a fully furnished, turnkey waterfront escape offering luxury, privacy, and unforgettable Chesapeake Bay sunsets, all within the laid-back charm and timeless appeal that make Tilghman Island so special.

5698 Leeward Ln, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Stuart & Maury, Inc..

$1,250,000

A storybook waterfront home with privacy, and timeless old-world charm. This Tilghman Island waterfront property carries a gracious, welcoming spirit: peaceful, and full of character. Large rooms, tall presence, mature trees, and a beautiful wraparound porch give the home a timeless, almost cinematic quality. Set down a long private driveway on Broad Cove, which connects to Harris Creek, this secluded 4-bedroom, 2.5-bath home offers 3,037 square feet of generous living space, 438+ feet of shoreline and a swimming pool. Inside, the home offers expansive gathering spaces, including a large living room with a grand wood-burning fireplace, a spacious family room, a kitchen with a wood stove, and a generous primary bedroom with its own wood-burning fireplace. There is warmth and scale throughout. Old charm, big rooms, and the kind of relaxed elegance that is hard to recreate. A dock is in place and in need of repair, offering the next owner the opportunity to restore and customize the waterfront experience. Gracious, private, and full of soul, this rare Broad Cove property offers the presence and romance of a true dream home. Note: Original section of home has asbestos-cement exterior shingles.

4 Beds ⋅ 3 Baths

A storybook waterfront home with privacy, and timeless old-world charm. This Tilghman Island waterfront property carries a gracious, welcoming spirit: peaceful, and full of character. Large rooms, tall presence, mature trees, and a beautiful wraparound porch give the home a timeless, almost cinematic quality. Set down a long private driveway on Broad Cove, which connects to Harris Creek, this secluded 4-bedroom, 2.5-bath home offers 3,037 square feet of generous living space, 438+ feet of shoreline and a swimming pool. Inside, the home offers expansive gathering spaces, including a large living room with a grand wood-burning fireplace, a spacious family room, a kitchen with a wood stove, and a generous primary bedroom with its own wood-burning fireplace. There is warmth and scale throughout. Old charm, big rooms, and the kind of relaxed elegance that is hard to recreate. A dock is in place and in need of repair, offering the next owner the opportunity to restore and customize the waterfront experience. Gracious, private, and full of soul, this rare Broad Cove property offers the presence and romance of a true dream home. Note: Original section of home has asbestos-cement exterior shingles.

21408 Broad Cove Ln, Tilghman

Listing courtesy of Compass. Contact:

Selling Office: Northrop Realty.

$1,075,000

Experience waterfront living in the historic community of Fairbank on Tilghman Island. This home offers timeless character and sweeping views of Black Walnut Cove. Built in 1900 with later additions, you'll find multiple decks, porches, and patios, along with a unique circular staircase leading to the second-floor porch, enhancing its architectural charm. Inside, the gourmet kitchen and family room provide a central gathering space with expansive water views, granite countertops, and custom cabinetry. A secondary kitchen provides added convenience for entertaining. The owners have invested in significant updates, including new two-stage heat pumps with UV filter and whole-house dehumidifier, fresh interior paint throughout, refinished hardwood floors, and an encapsulated crawlspace for efficiency. The second floor offers three bedrooms and full bath. On the third floor you will find your Owner's Suite with views to your private dock and en-suite bathroom with tile shower. Outdoor amenities include a boat ramp, dock with water and electric, and floating dock making days on the water simple and enjoyable. The side yard of the home offers a firepit and ample space for a pool. With over 3,500 square feet and these amenities, this home presents a great opportunity for your Eastern Shore retreat or short term vacation rental, with approval.

4 Beds ⋅ 3 Baths

Experience waterfront living in the historic community of Fairbank on Tilghman Island. This home offers timeless character and sweeping views of Black Walnut Cove. Built in 1900 with later additions, you'll find multiple decks, porches, and patios, along with a unique circular staircase leading to the second-floor porch, enhancing its architectural charm. Inside, the gourmet kitchen and family room provide a central gathering space with expansive water views, granite countertops, and custom cabinetry. A secondary kitchen provides added convenience for entertaining. The owners have invested in significant updates, including new two-stage heat pumps with UV filter and whole-house dehumidifier, fresh interior paint throughout, refinished hardwood floors, and an encapsulated crawlspace for efficiency. The second floor offers three bedrooms and full bath. On the third floor you will find your Owner's Suite with views to your private dock and en-suite bathroom with tile shower. Outdoor amenities include a boat ramp, dock with water and electric, and floating dock making days on the water simple and enjoyable. The side yard of the home offers a firepit and ample space for a pool. With over 3,500 square feet and these amenities, this home presents a great opportunity for your Eastern Shore retreat or short term vacation rental, with approval.

21368 Fairbank Cir, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: AB & Co Realtors, Inc..

$1,050,000

Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

3 Beds ⋅ 3 Baths

Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

6050 Sunset Ln, Tilghman

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

Selling Office: Benson & Mangold, LLC.

$1,000,000

Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ceilings—all connected by elegant sight lines and polished hardwoods. A true chef’s kitchen anchors the heart of the home, outfitted with a commercial-grade gas stove, a commercial refrigerator, two dishwashers, granite countertops, and an oversized island perfect for entertaining or casual morning coffee. The main-level primary suite is a private retreat, offering dual walk-in closets, a spa-inspired bath with soaking tub and glass shower, and serene views of the surrounding landscape. A conveniently placed laundry room with a half bath adds thoughtful utility to the main floor, while the upstairs offers flexibility with four generous bedrooms, a shared full bath, and a secondary living space complete with its own kitchenette—ideal for extended guests or multigenerational living. From nearly every room, you're drawn to the shimmering water just beyond the windows. Whether enjoying sunsets from the deck, stargazing from the rooftop deck above the three-car garage, or savoring peaceful mornings with the birdsong of the bay, this home embraces its setting with elegance and ease. Attic storage above the garage ensures ample space for seasonal gear or future creative use. Tilghman Island itself is a captivating enclave, celebrated for its maritime heritage, vibrant wildlife, and relaxed coastal vibe. Here, you’ll enjoy unmatched privacy, historic charm, and proximity to waterfront dining, boutique shops, and world-class boating—just far enough to escape, yet close enough to stay connected. 5520 Leeward Lane isn’t just a home—it’s a lifestyle. A sanctuary where land, sea, and sky converge in perfect harmony. Schedule your private showing and experience Eastern Shore living redefined.

5 Beds ⋅ 3 Baths

Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ceilings—all connected by elegant sight lines and polished hardwoods. A true chef’s kitchen anchors the heart of the home, outfitted with a commercial-grade gas stove, a commercial refrigerator, two dishwashers, granite countertops, and an oversized island perfect for entertaining or casual morning coffee. The main-level primary suite is a private retreat, offering dual walk-in closets, a spa-inspired bath with soaking tub and glass shower, and serene views of the surrounding landscape. A conveniently placed laundry room with a half bath adds thoughtful utility to the main floor, while the upstairs offers flexibility with four generous bedrooms, a shared full bath, and a secondary living space complete with its own kitchenette—ideal for extended guests or multigenerational living. From nearly every room, you're drawn to the shimmering water just beyond the windows. Whether enjoying sunsets from the deck, stargazing from the rooftop deck above the three-car garage, or savoring peaceful mornings with the birdsong of the bay, this home embraces its setting with elegance and ease. Attic storage above the garage ensures ample space for seasonal gear or future creative use. Tilghman Island itself is a captivating enclave, celebrated for its maritime heritage, vibrant wildlife, and relaxed coastal vibe. Here, you’ll enjoy unmatched privacy, historic charm, and proximity to waterfront dining, boutique shops, and world-class boating—just far enough to escape, yet close enough to stay connected. 5520 Leeward Lane isn’t just a home—it’s a lifestyle. A sanctuary where land, sea, and sky converge in perfect harmony. Schedule your private showing and experience Eastern Shore living redefined.

5520 Leeward Ln, Tilghman

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$740,000

Welcome to 5820 Tilghman Beach Drive. Come experience the most beautiful sunsets the Chesapeake Bay has to offer. Centrally located on Tilghman Island this little slice of paradise is ready for its new owners to make their dream of waterfront living come true. Home offers two bedrooms and one full bath, hardwood floors, recently remodeled kitchen, encapsuled crawl space, Central heat and air, two car garage. The large bayfront yard offers many possibilities. Plan your visit today.

2 Beds ⋅ 1 Baths

Welcome to 5820 Tilghman Beach Drive. Come experience the most beautiful sunsets the Chesapeake Bay has to offer. Centrally located on Tilghman Island this little slice of paradise is ready for its new owners to make their dream of waterfront living come true. Home offers two bedrooms and one full bath, hardwood floors, recently remodeled kitchen, encapsuled crawl space, Central heat and air, two car garage. The large bayfront yard offers many possibilities. Plan your visit today.

5820 Tilghman Beach Dr, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented Buyer Office.

$725,000

Spacious 3,000 sqft two-story waterfront home on 3/4 acre parcel on Harris Creek where it joins the Choptank River for an 11-mile view to Cambridge. House is brick and block on the first level with redwood siding on the second level in board and batten style. 150ft heavily built and reinforced bulkhead waterfront with recently renovated 75ft long dock. Second floor includes four bedrooms with water views and a bunk room all with oak flooring recently refinished, built-in chest of drawers and closets, built in desks and bookcases. Second floor includes a great room with cathedral ceiling and outside deck facing Harris Creek, a full bath and powder room, all tiled. First floor has open area kitchen, dining/living room with adjacent full bath and utility room. Kitchen has been dismantled as a clean pallet for new owner, bring your vision. First and second floor have fireplaces with separate flues. Full attic. 700sqft attached garage and workshop. Property is equipped with a Generac generator for dependable backup power. There is an offshore duck blind for waterfowl & duck hunting which is shared with neighboring owners. Enjoy panoramic water views, boating, crabbing, fishing year-round. Experience the waterfront charm and relaxed pace of Tilghman Island living, close to museums, restaurants, shopping and marinas, truly a wonderful place to call home! Offers encouraged.

4 Beds ⋅ 3 Baths

Spacious 3,000 sqft two-story waterfront home on 3/4 acre parcel on Harris Creek where it joins the Choptank River for an 11-mile view to Cambridge. House is brick and block on the first level with redwood siding on the second level in board and batten style. 150ft heavily built and reinforced bulkhead waterfront with recently renovated 75ft long dock. Second floor includes four bedrooms with water views and a bunk room all with oak flooring recently refinished, built-in chest of drawers and closets, built in desks and bookcases. Second floor includes a great room with cathedral ceiling and outside deck facing Harris Creek, a full bath and powder room, all tiled. First floor has open area kitchen, dining/living room with adjacent full bath and utility room. Kitchen has been dismantled as a clean pallet for new owner, bring your vision. First and second floor have fireplaces with separate flues. Full attic. 700sqft attached garage and workshop. Property is equipped with a Generac generator for dependable backup power. There is an offshore duck blind for waterfowl & duck hunting which is shared with neighboring owners. Enjoy panoramic water views, boating, crabbing, fishing year-round. Experience the waterfront charm and relaxed pace of Tilghman Island living, close to museums, restaurants, shopping and marinas, truly a wonderful place to call home! Offers encouraged.

5489 Rude Ave, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Tilghman Island Realty Inc.

$560,000

Charming 2-3BR/2BA coastal cottage with tranquil water views of Black Walnut Cove and the Choptank River - ideal for easy full-time living or a relaxed weekend retreat. Beautiful hardwood floors run throughout, complementing the home’s warm, welcoming character and comfortable scale. The living room, anchored by a wood-burning fireplace, offers a cozy gathering space, while the kitchen is thoughtfully designed with a large center island, wet bar, and French door access to a beautiful screened porch overlooking the cove - perfect for morning coffee, quiet afternoons, or casual evening entertaining. The primary suite is a peaceful retreat, featuring an ensuite bath, walk-in closet, and convenient laundry cubby. An adjoining second bedroom offers flexibility as a private office, sitting room, or additional sleeping space. A third bedroom and full hall bath provide comfortable accommodation for guests. Additional highlights include a garden shed and a fully conditioned “she shed” with heat and AC, currently used as an art studio – a versatile space for hobbies or creative pursuits. Numerous improvements include a new roof, Pella architectural windows, encapsulated crawlspace, 3-zone Mitsubishi mini-split system, reverse-osmosis water filtration, and more. This thoughtfully updated cottage offers the best of Eastern Shore living with a relaxed, waterside feel.

2 Beds ⋅ 2 Baths

Charming 2-3BR/2BA coastal cottage with tranquil water views of Black Walnut Cove and the Choptank River - ideal for easy full-time living or a relaxed weekend retreat. Beautiful hardwood floors run throughout, complementing the home’s warm, welcoming character and comfortable scale. The living room, anchored by a wood-burning fireplace, offers a cozy gathering space, while the kitchen is thoughtfully designed with a large center island, wet bar, and French door access to a beautiful screened porch overlooking the cove - perfect for morning coffee, quiet afternoons, or casual evening entertaining. The primary suite is a peaceful retreat, featuring an ensuite bath, walk-in closet, and convenient laundry cubby. An adjoining second bedroom offers flexibility as a private office, sitting room, or additional sleeping space. A third bedroom and full hall bath provide comfortable accommodation for guests. Additional highlights include a garden shed and a fully conditioned “she shed” with heat and AC, currently used as an art studio – a versatile space for hobbies or creative pursuits. Numerous improvements include a new roof, Pella architectural windows, encapsulated crawlspace, 3-zone Mitsubishi mini-split system, reverse-osmosis water filtration, and more. This thoughtfully updated cottage offers the best of Eastern Shore living with a relaxed, waterside feel.

4940 Fairbank Rd, Tilghman

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

Selling Office: Redfin Corp.

$523,307

Welcome to 5582 Trafalgar Cir (truh-FAL-gar), a beautifully maintained single-level, 3-bedroom, 2.5-bath home located in the desirable Tilghman on Chesapeake community. Built in 2023 and offering 2,110 square feet of thoughtfully designed living space, this home has been lived in for only about a year and truly shows better than new. The seller’s meticulous care and attention to detail have addressed the typical quirks of new construction, creating a move-in-ready home with refined comfort throughout. Designed for easy one-level living, the open floor plan centers around a spacious Great Room that flows seamlessly into the kitchen and dining area—ideal for both everyday living and entertaining. The kitchen features a large island, generous cabinetry, and ample counter space. The private owner’s suite provides a peaceful retreat with a walk-in closet and a well-appointed en-suite bath with dual vanities. Two additional bedrooms, a full hall bath, a convenient half bath, and a dedicated laundry area complete the layout. Step outside to an oversized deck, perfect for outdoor dining, relaxing, or hosting gatherings while enjoying community water access and a small water view. Whether you’re sipping your morning coffee or unwinding in the evening, the outdoor space enhances the home’s connection to the Chesapeake Bay lifestyle. Tilghman on Chesapeake is a water-oriented community offering amenities that include a clubhouse, pool, and marina access, all just minutes from local marinas, seafood restaurants, and the charm of Tilghman Island. This is a rare opportunity to own a like-new, single-story home with exceptional outdoor living in one of the Eastern Shore’s most sought-after waterfront communities.

3 Beds ⋅ 3 Baths

Welcome to 5582 Trafalgar Cir (truh-FAL-gar), a beautifully maintained single-level, 3-bedroom, 2.5-bath home located in the desirable Tilghman on Chesapeake community. Built in 2023 and offering 2,110 square feet of thoughtfully designed living space, this home has been lived in for only about a year and truly shows better than new. The seller’s meticulous care and attention to detail have addressed the typical quirks of new construction, creating a move-in-ready home with refined comfort throughout. Designed for easy one-level living, the open floor plan centers around a spacious Great Room that flows seamlessly into the kitchen and dining area—ideal for both everyday living and entertaining. The kitchen features a large island, generous cabinetry, and ample counter space. The private owner’s suite provides a peaceful retreat with a walk-in closet and a well-appointed en-suite bath with dual vanities. Two additional bedrooms, a full hall bath, a convenient half bath, and a dedicated laundry area complete the layout. Step outside to an oversized deck, perfect for outdoor dining, relaxing, or hosting gatherings while enjoying community water access and a small water view. Whether you’re sipping your morning coffee or unwinding in the evening, the outdoor space enhances the home’s connection to the Chesapeake Bay lifestyle. Tilghman on Chesapeake is a water-oriented community offering amenities that include a clubhouse, pool, and marina access, all just minutes from local marinas, seafood restaurants, and the charm of Tilghman Island. This is a rare opportunity to own a like-new, single-story home with exceptional outdoor living in one of the Eastern Shore’s most sought-after waterfront communities.

5582 Trafalgar Cir, Tilghman

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$510,000

Bay Breezes & Beautiful Views: Your Tilghman Island Haven Waterview Living with Room to Breathe on Maryland's Eastern Shore Step into the good life at 5379 Anchor Road, where Chesapeake Bay magic meets everyday comfort. This charming home in Tilghman's friendly beach neighborhood sits just a short stroll from the community beach where neighbors gather and memories are made. Picture yourself unwinding on the deck with morning coffee, watching the sun sparkle across the bay waters. Inside, the welcoming home greets you with warm hardwood floors throughout, two comfortable bedrooms, and two full baths. The kitchen is a joy to cook in—featuring granite countertops, stainless appliances, and beautiful hand-crafted wood cabinets perfect for whipping up fresh seafood dinners or casual breakfasts before heading out to explore the water. What makes this place truly special is the adorable guest cottage built in 2017. This sweet retreat offers a screened porch with more water views, its own heating and cooling, and a half bath—perfect for visiting friends or your own creative escape when you need a moment to yourself. For water lovers, you're in paradise—grab your kayak or paddleboard and launch right from your backyard. Gardening opportunities abound-whether ornamental or the fun of your own fresh summer veggies-the property also includes fruit trees -pies and jams in your future? The practical perks are all here too: a roomy two-car garage with workshop space for projects, outdoor shower for rinsing off sandy feet, beautiful landscaping, plus recent updates including a new roof (2018) and HVAC system (2016) so you can relax knowing the essentials are taken care of. Beyond your doorstep, discover the authentic charm of Tilghman Island. A short, scenic drive connects you to the fabulous restaurants, shops and galleries of St. Michaels, Easton, and Oxford. When you choose this Tilghman Island home, you're investing in more than just real estate—you're gaining a lifestyle where stress melts away with each bay breeze and sunset. Whether you're looking for a full-time home with vacation vibes, a weekend getaway from the city grind, or the perfect spot to eventually retire and watch the osprey soar, this special place offers what so many of us are searching for—a chance to slow down, breathe deeply, and connect with the beauty of the bay. Come see what life on Tilghman time feels like. Your Eastern Shore story is waiting to begin.

2 Beds ⋅ 3 Baths

Bay Breezes & Beautiful Views: Your Tilghman Island Haven Waterview Living with Room to Breathe on Maryland's Eastern Shore Step into the good life at 5379 Anchor Road, where Chesapeake Bay magic meets everyday comfort. This charming home in Tilghman's friendly beach neighborhood sits just a short stroll from the community beach where neighbors gather and memories are made. Picture yourself unwinding on the deck with morning coffee, watching the sun sparkle across the bay waters. Inside, the welcoming home greets you with warm hardwood floors throughout, two comfortable bedrooms, and two full baths. The kitchen is a joy to cook in—featuring granite countertops, stainless appliances, and beautiful hand-crafted wood cabinets perfect for whipping up fresh seafood dinners or casual breakfasts before heading out to explore the water. What makes this place truly special is the adorable guest cottage built in 2017. This sweet retreat offers a screened porch with more water views, its own heating and cooling, and a half bath—perfect for visiting friends or your own creative escape when you need a moment to yourself. For water lovers, you're in paradise—grab your kayak or paddleboard and launch right from your backyard. Gardening opportunities abound-whether ornamental or the fun of your own fresh summer veggies-the property also includes fruit trees -pies and jams in your future? The practical perks are all here too: a roomy two-car garage with workshop space for projects, outdoor shower for rinsing off sandy feet, beautiful landscaping, plus recent updates including a new roof (2018) and HVAC system (2016) so you can relax knowing the essentials are taken care of. Beyond your doorstep, discover the authentic charm of Tilghman Island. A short, scenic drive connects you to the fabulous restaurants, shops and galleries of St. Michaels, Easton, and Oxford. When you choose this Tilghman Island home, you're investing in more than just real estate—you're gaining a lifestyle where stress melts away with each bay breeze and sunset. Whether you're looking for a full-time home with vacation vibes, a weekend getaway from the city grind, or the perfect spot to eventually retire and watch the osprey soar, this special place offers what so many of us are searching for—a chance to slow down, breathe deeply, and connect with the beauty of the bay. Come see what life on Tilghman time feels like. Your Eastern Shore story is waiting to begin.

5379 Anchor Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Tilghman Island Realty Inc.

$455,000

3 Beds ⋅ 2 Baths

5654 Trafalgar Cir, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Northrop Realty.

$411,000

2 year old cottage located on Tilghman Island. 3 bedrooms and 2.5 baths, this property is perfect for full time residents or for weekend getaways. Property is located on a quite cul-de-sac and backs up to trees. Large open living room, dining area and kitchen provides enough space for family gatherings or entertaining friends. Kitchen has granite counters and stainless appliances along with a large pantry. There is a reverse osmosis water filter attached to the kitchen faucet. The primary bedroom with attached full bath is on the main level. Also on the main level is a half bath and a laundry room with stainless steel stackable wash and dryer. Also an iron removing water filter in the laundry room. Upstairs are two large bedrooms that share a full bathroom. Each upstairs bedroom has its own mini split heating and air unit. There is an outdoor shed for additional storage. This property is large enough for your future expansion projects like a garage or pool.

3 Beds ⋅ 3 Baths

2 year old cottage located on Tilghman Island. 3 bedrooms and 2.5 baths, this property is perfect for full time residents or for weekend getaways. Property is located on a quite cul-de-sac and backs up to trees. Large open living room, dining area and kitchen provides enough space for family gatherings or entertaining friends. Kitchen has granite counters and stainless appliances along with a large pantry. There is a reverse osmosis water filter attached to the kitchen faucet. The primary bedroom with attached full bath is on the main level. Also on the main level is a half bath and a laundry room with stainless steel stackable wash and dryer. Also an iron removing water filter in the laundry room. Upstairs are two large bedrooms that share a full bathroom. Each upstairs bedroom has its own mini split heating and air unit. There is an outdoor shed for additional storage. This property is large enough for your future expansion projects like a garage or pool.

5744 Johns Way, Tilghman

Listing courtesy of Tilghman Island Realty Inc. Contact:

Selling Office: Meredith Fine Properties.

$400,000

This historic property known as "The Elms" was built in 1900 and originally used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water and consists of three buildings which are: The original main building, the detached garage and a shed/storage building. The buildings hold virtually no value unless an extensive historic renovation were completed, but the opportunity is fantastic. Tilghman is an historic waterfront town that features a waterman's museum, marina, many restaurants, and established neighborhoods/communities such as Tilghman on the Chesapeake, Fairbanks, and Black Walnut Point. In addition to restoring the buildings, there may be opportunity to build new. A truly iconic piece of Tilghman history. Property being sold "As-Is."

9 Beds ⋅ 3 Baths

This historic property known as "The Elms" was built in 1900 and originally used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water and consists of three buildings which are: The original main building, the detached garage and a shed/storage building. The buildings hold virtually no value unless an extensive historic renovation were completed, but the opportunity is fantastic. Tilghman is an historic waterfront town that features a waterman's museum, marina, many restaurants, and established neighborhoods/communities such as Tilghman on the Chesapeake, Fairbanks, and Black Walnut Point. In addition to restoring the buildings, there may be opportunity to build new. A truly iconic piece of Tilghman history. Property being sold "As-Is."

21486 Mission Rd, Tilghman

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

Selling Office: Meredith Fine Properties.

$375,000

TILGHMAN ISLAND: Discover your dream home in the charming, water-privileged community of Tilghman Beach. This stunning ranch-style home, built in 2018, offers modern conveniences and one-level living at its finest, perfect for those seeking a serene lifestyle by the water. Key Features: Spacious Open Floor Plan: Enjoy seamless living with a large combination living and dining area, ideal for entertaining or relaxing. Owner's Suite Retreat: The owner's suite is thoughtfully positioned on one side of the home, complete with a private bath for your ultimate comfort. Additional Bedrooms: Two additional well-sized bedrooms and a full bath are located on the opposite side, offering privacy for family or guests. Gourmet Kitchen: Cook up a storm in the stylish kitchen that boasts stainless steel appliances, a gas range, and a center island that doubles as a gathering spot. Outdoor Living: Step out onto the back yard deck, where you can take in glimpses of the water and enjoy space for your garden or outdoor activities. Take advantage of the community’s beach access, where you can create cherished memories while kayaking, canoeing, paddleboarding, or fishing on the picturesque Chesapeake Bay. Don’t miss out on this incredible opportunity! Schedule your appointment today to see this beautiful home and make it yours!

3 Beds ⋅ 2 Baths

TILGHMAN ISLAND: Discover your dream home in the charming, water-privileged community of Tilghman Beach. This stunning ranch-style home, built in 2018, offers modern conveniences and one-level living at its finest, perfect for those seeking a serene lifestyle by the water. Key Features: Spacious Open Floor Plan: Enjoy seamless living with a large combination living and dining area, ideal for entertaining or relaxing. Owner's Suite Retreat: The owner's suite is thoughtfully positioned on one side of the home, complete with a private bath for your ultimate comfort. Additional Bedrooms: Two additional well-sized bedrooms and a full bath are located on the opposite side, offering privacy for family or guests. Gourmet Kitchen: Cook up a storm in the stylish kitchen that boasts stainless steel appliances, a gas range, and a center island that doubles as a gathering spot. Outdoor Living: Step out onto the back yard deck, where you can take in glimpses of the water and enjoy space for your garden or outdoor activities. Take advantage of the community’s beach access, where you can create cherished memories while kayaking, canoeing, paddleboarding, or fishing on the picturesque Chesapeake Bay. Don’t miss out on this incredible opportunity! Schedule your appointment today to see this beautiful home and make it yours!

5440 Anchor Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Douglas Realty LLC.

$350,000

Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on Maryland's Chesapeake Bay. The backyard pool is a highlight, offering a tranquil setting that is worth the price of admission. Relax poolside after a day spent fishing, crabbing, or sailing. Additionally, a large shed provides ample storage for all your needs. This property also presents a great investment opportunity for short-term rental or as a retirement home. Don’t miss out on this one! Make your appointment today.

2 Beds ⋅ 1 Baths

Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on Maryland's Chesapeake Bay. The backyard pool is a highlight, offering a tranquil setting that is worth the price of admission. Relax poolside after a day spent fishing, crabbing, or sailing. Additionally, a large shed provides ample storage for all your needs. This property also presents a great investment opportunity for short-term rental or as a retirement home. Don’t miss out on this one! Make your appointment today.

6135 Summit St, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: RE/MAX Chesapeake.

$345,000

Charming, Fully Updated Cottage on Tilghman Island – Move-In Ready! Spend the rest of your summer enjoying the relaxed lifestyle that makes Tilghman Island so special. This beautifully updated cottage is move-in ready and is conveniently located within walking or biking distance of three popular waterfront restaurants, marinas, shops, and everything this charming Chesapeake Bay community has to offer. A welcoming front porch with a classic porch swing provides the perfect place to relax with your morning coffee or unwind on a warm summer evening. Inside, you'll find a bright, open living and dining area that creates an inviting space for entertaining family and friends. The sun-filled country kitchen offers abundant natural light, generous cabinet space, and a spacious pantry with an adjoining laundry area. The first floor also features a comfortable bedroom and a beautifully updated full bath, making it ideal for one-level living or a primary suite. Upstairs are two additional bedrooms, perfect for family, guests, or a home office. Lovingly maintained and thoughtfully updated, this home has been a cherished gathering place for years. Recent improvements include all-new energy-efficient mini-split systems that provide comfortable heating and cooling throughout the home. Whether you're looking for a full-time residence, a weekend getaway, or a vacation rental opportunity, this charming cottage offers endless possibilities. Don't miss your chance to own a piece of Tilghman Island—schedule your private showing today before this delightful home is gone!

3 Beds ⋅ 1 Baths

Charming, Fully Updated Cottage on Tilghman Island – Move-In Ready! Spend the rest of your summer enjoying the relaxed lifestyle that makes Tilghman Island so special. This beautifully updated cottage is move-in ready and is conveniently located within walking or biking distance of three popular waterfront restaurants, marinas, shops, and everything this charming Chesapeake Bay community has to offer. A welcoming front porch with a classic porch swing provides the perfect place to relax with your morning coffee or unwind on a warm summer evening. Inside, you'll find a bright, open living and dining area that creates an inviting space for entertaining family and friends. The sun-filled country kitchen offers abundant natural light, generous cabinet space, and a spacious pantry with an adjoining laundry area. The first floor also features a comfortable bedroom and a beautifully updated full bath, making it ideal for one-level living or a primary suite. Upstairs are two additional bedrooms, perfect for family, guests, or a home office. Lovingly maintained and thoughtfully updated, this home has been a cherished gathering place for years. Recent improvements include all-new energy-efficient mini-split systems that provide comfortable heating and cooling throughout the home. Whether you're looking for a full-time residence, a weekend getaway, or a vacation rental opportunity, this charming cottage offers endless possibilities. Don't miss your chance to own a piece of Tilghman Island—schedule your private showing today before this delightful home is gone!

21527 Chicken Point Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

$275,000

A fantastic opportunity awaits at 21749 Camper Circle in Tilghman, Maryland. This home is perfect for first-time buyers or investors looking for great value at an affordable price. It features central heating and air conditioning, three spacious bedrooms, and one full bathroom. Enjoy a large sunroom with tile flooring that is conveniently located next to the kitchen. The hardwood floors throughout the home are in excellent condition, adding to the charm of the open layout. Additionally, there is a full basement that offers numerous potential uses. This property is conveniently located within walking distance of marinas and three of the best restaurants in Tilghman, making it a must-see!

3 Beds ⋅ 1 Baths

A fantastic opportunity awaits at 21749 Camper Circle in Tilghman, Maryland. This home is perfect for first-time buyers or investors looking for great value at an affordable price. It features central heating and air conditioning, three spacious bedrooms, and one full bathroom. Enjoy a large sunroom with tile flooring that is conveniently located next to the kitchen. The hardwood floors throughout the home are in excellent condition, adding to the charm of the open layout. Additionally, there is a full basement that offers numerous potential uses. This property is conveniently located within walking distance of marinas and three of the best restaurants in Tilghman, making it a must-see!

21749 Camper Cir, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Keller Williams Select Realtors of Cambridge.

$265,000

This charming Tilghman Island cottage was originally built in 1953 and thoughtfully renovated in 2020, including updated plumbing and electric. The home features durable luxury vinyl plank flooring throughout and the roof was replaced with 45-year architectural shingles for added peace of mind. The kitchen offers stainless steel appliances, space for a dining table and flows seamlessly into the spacious living room, ideal for everyday living and entertaining. The flexible floor plan includes 2–3 bedrooms and a full bath with a shower. The attic presents an opportunity for expansion, perfect for creating a loft or additional bedroom. Outside, enjoy a partially fenced backyard complete with a large shed equipped with electric, ideal for storage, hobbies or a workshop. Situated on scenic Tilghman Island, this property is just moments from marinas and public boat landings, providing easy access to the Chesapeake Bay and surrounding waterways for boating, fishing, and waterfront dining.

3 Beds ⋅ 1 Baths

This charming Tilghman Island cottage was originally built in 1953 and thoughtfully renovated in 2020, including updated plumbing and electric. The home features durable luxury vinyl plank flooring throughout and the roof was replaced with 45-year architectural shingles for added peace of mind. The kitchen offers stainless steel appliances, space for a dining table and flows seamlessly into the spacious living room, ideal for everyday living and entertaining. The flexible floor plan includes 2–3 bedrooms and a full bath with a shower. The attic presents an opportunity for expansion, perfect for creating a loft or additional bedroom. Outside, enjoy a partially fenced backyard complete with a large shed equipped with electric, ideal for storage, hobbies or a workshop. Situated on scenic Tilghman Island, this property is just moments from marinas and public boat landings, providing easy access to the Chesapeake Bay and surrounding waterways for boating, fishing, and waterfront dining.

21530 Coopertown Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$60,000

Build your dream home on beautiful Tilghman Island! This ideally located lot is within walking distance of Sinclair Community Park, local marinas, charming shops, and popular waterfront restaurants. Stroll to the end of your street to enjoy stunning Chesapeake Bay sunsets from the park’s scenic shoreline. Tilghman Island is a beloved Eastern Shore destination known for its rich maritime heritage, working harbor, and friendly small-town atmosphere. Residents and visitors alike enjoy boating, fishing, kayaking, crabbing, and biking along quiet country roads. The island offers a relaxed coastal lifestyle while still being only a short drive to St. Michaels and other Bay communities. Public sewer connection available, making the building process straightforward and convenient. Don’t miss this opportunity to own a piece of island life—perfect for a full-time residence or a serene getaway by the Bay.

Sinclair Avenue, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

How much is your home worth?

How much is your home worth?