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BE SURE TO WATCH THE VIDEO TOUR TO EXPERIENCE THE PROPERTY AND SETTING. Rare opportunity in the coveted Village of Fairbank on Tilghman Island. Set on nearly an acre in a peaceful Eastern Shore setting, this charming 1900 traditional home offers 1,720 square feet of living space with three bedrooms, two full baths, and the warmth and character of a wood-burning fireplace. One of the property's most distinctive features is its setting along Black Walnut Cove, just beyond the backyard, offering an idyllic backdrop for kayaking, canoeing, and enjoying life near the water. The expansive .93-acre lot provides plenty of room for outdoor entertaining, gardening, or simply relaxing and taking in the natural surroundings. Fairbank on Tilghman is a special community where neighbors know one another and take care of eachother. Whether you're searching for a full-time residence or a weekend retreat, this property offers a wonderful opportunity to enjoy the character of Tilghman Island, the beauty of the Chesapeake Bay region, and a lifestyle centered around the water. Just minutes from the restaurants, marinas, and charm of Tilghman Island, 23180 Fairbank Circle is an opportunity to make this unique Eastern Shore community your own. Located 20 minutes from St. Michaels!

3 Beds ⋅ 2 Baths

BE SURE TO WATCH THE VIDEO TOUR TO EXPERIENCE THE PROPERTY AND SETTING. Rare opportunity in the coveted Village of Fairbank on Tilghman Island. Set on nearly an acre in a peaceful Eastern Shore setting, this charming 1900 traditional home offers 1,720 square feet of living space with three bedrooms, two full baths, and the warmth and character of a wood-burning fireplace. One of the property's most distinctive features is its setting along Black Walnut Cove, just beyond the backyard, offering an idyllic backdrop for kayaking, canoeing, and enjoying life near the water. The expansive .93-acre lot provides plenty of room for outdoor entertaining, gardening, or simply relaxing and taking in the natural surroundings. Fairbank on Tilghman is a special community where neighbors know one another and take care of eachother. Whether you're searching for a full-time residence or a weekend retreat, this property offers a wonderful opportunity to enjoy the character of Tilghman Island, the beauty of the Chesapeake Bay region, and a lifestyle centered around the water. Just minutes from the restaurants, marinas, and charm of Tilghman Island, 23180 Fairbank Circle is an opportunity to make this unique Eastern Shore community your own. Located 20 minutes from St. Michaels!

21380 Fairbank Circle Cir, Tilghman

Listing courtesy of Compass. Contact:

$209,700

Discover a unique investment opportunity in the charming Victorian-style home located in the serene Tilghman Island. This detached residence, built in 1900, boasts 2 over/under units of well-maintained living space, each featuring a spacious bedroom and full bathroom. The interior is adorned with hardwood and partially carpeted floors, enhancing its classic appeal. Investors will appreciate the built-in features, energy-efficient double-pane windows, and a cozy gas fireplace, perfect for attracting quality tenants. The country-style kitchen is equipped with essential appliances, including a refrigerator, built-in microwave, oven/range, dishwasher, and washer/dryer, ensuring convenience for future occupants. The expansive 0.42-acre lot offers ample outdoor space, complemented by inviting patios and porches, ideal for relaxation or entertaining. With off-street parking and a shed for additional storage, this property is primed for rental income or long-term appreciation. Seize this chance to invest in a timeless gem with significant potential!

2 Beds ⋅ 2 Baths

Discover a unique investment opportunity in the charming Victorian-style home located in the serene Tilghman Island. This detached residence, built in 1900, boasts 2 over/under units of well-maintained living space, each featuring a spacious bedroom and full bathroom. The interior is adorned with hardwood and partially carpeted floors, enhancing its classic appeal. Investors will appreciate the built-in features, energy-efficient double-pane windows, and a cozy gas fireplace, perfect for attracting quality tenants. The country-style kitchen is equipped with essential appliances, including a refrigerator, built-in microwave, oven/range, dishwasher, and washer/dryer, ensuring convenience for future occupants. The expansive 0.42-acre lot offers ample outdoor space, complemented by inviting patios and porches, ideal for relaxation or entertaining. With off-street parking and a shed for additional storage, this property is primed for rental income or long-term appreciation. Seize this chance to invest in a timeless gem with significant potential!

4869 Bar Neck Rd, Tilghman

Listing courtesy of Maryland Realty Connection. Contact:

$410,000

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

4 Beds ⋅ 3 Baths

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

21406 Dogwood Cove Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

$449,900

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

3 Beds ⋅ 3 Baths

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

5933 Tilghman Island Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

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