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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:

$470,000

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:

$339,000

Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic "W" homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bath—ideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty of space for family and friends. A new HVAC system adds year-round comfort, while the generous yard offers room for gardening, entertaining, or simply relaxing after a day on the water. Whether you're searching for a full-time residence, a weekend retreat, or an investment in one of the Eastern Shore's most charming villages, this home delivers exceptional value at an attractive price point. Experience the slower pace, rich maritime heritage, and unmatched sense of community that make Tilghman Island one of the Chesapeake Bay's hidden gems.

4 Beds ⋅ 2 Baths

Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic "W" homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bath—ideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty of space for family and friends. A new HVAC system adds year-round comfort, while the generous yard offers room for gardening, entertaining, or simply relaxing after a day on the water. Whether you're searching for a full-time residence, a weekend retreat, or an investment in one of the Eastern Shore's most charming villages, this home delivers exceptional value at an attractive price point. Experience the slower pace, rich maritime heritage, and unmatched sense of community that make Tilghman Island one of the Chesapeake Bay's hidden gems.

21524 Chicken Point Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: