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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.

$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.

$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.

$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.

$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.

$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.

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How much is your home worth?