Tilghman Real Estate

Tilghman Real Estate

Welcome to Tilghman, Maryland—a hidden gem nestled on the eastern shore of the Chesapeake Bay in Talbot County. This charming waterfront community offers a unique blend of tranquility, rich history, and natural beauty, making it an ideal place to call home.

Tilghman is renowned for its picturesque landscapes, with stunning views of the bay and lush greenery that surrounds the area. The town exudes a quaint, small-town charm, where friendly neighbors greet you with a smile and local businesses thrive. With a population of just a few hundred residents, Tilghman fosters a strong sense of community, making it perfect for those seeking a peaceful retreat away from the hustle and bustle of city life.

Outdoor enthusiasts will find Tilghman to be a paradise, with ample opportunities for boating, fishing, and kayaking. The area is dotted with marinas and waterfront parks, inviting residents to embrace the beauty of the Chesapeake Bay. Additionally, the nearby Tilghman Island offers historical sites and nature trails, perfect for a leisurely stroll or a day of exploration.

Culinary delights await you at local eateries, where you can savor fresh seafood caught right from the bay. The rich maritime culture of Tilghman is evident in its annual events and festivals, celebrating its heritage and the vibrant spirit of the community.

Whether you're looking to retire, relocate, or invest, Tilghman, MD, offers a serene lifestyle filled with charm and character. Come discover your new home in this idyllic coastal town, where every day feels like a vacation.

Newest Listings in Tilghman

$939,900
3 Beds ⋅ 2 Baths
Tucked away beneath a canopy of mature trees, 6114 Sunset Lane feels like a storybook retreat along the shores of the Chesapeake Bay. A tree-lined, pebbled circular driveway welcomes you home, setting the tone for the quiet beauty and sense of escape found throughout this special waterfront property. Surrounded by nature and framed by peaceful water views, the home offers a slower, more intentional way of living. Begin your mornings with sunlight dancing across the bay, spend your afternoons enjoying the gentle rhythm of the water, and end each day beneath the soft colors of an Eastern Shore sunset. Inside, abundant natural light pours through the home, creating bright, inviting spaces that feel effortlessly connected to the surrounding landscape. The thoughtfully renovated three-bedroom, two-full-bathroom residence blends timeless character with elevated modern comfort. At the heart of the home is the beautifully renovated kitchen, where rich soapstone countertops bring natural warmth, depth, and understated sophistication to the space. Bathed in sunlight, the kitchen feels equally suited for quiet morning coffee, preparing meals with family, or gathering with friends after a day spent near the water. The renovated bathrooms continue the home’s refined design, offering calming, thoughtfully finished spaces that complement the serenity of the setting. A spacious two-car garage provides convenient parking and additional storage, while the circular driveway creates a graceful arrival with plenty of room to welcome guests. Beyond the home, the property’s lush surroundings offer an atmosphere that feels private, peaceful, and wonderfully removed from the noise of everyday life. Whether imagined as a full-time residence, a weekend escape, or a cherished gathering place for family and friends, 6114 Sunset Lane is more than a waterfront home, it is a place to exhale, reconnect with nature, and create lasting memories along the Chesapeake Bay.

6114 Sunset Ln, Tilghman

Listing courtesy of Compass. Contact: (202) 386-6330
$1,895,000
Very rare opportunity to buy 36+/- acres with stunning views of the Chesapeake Bay. Approximately 2,100 feet of rip-rapped shoreline. Property is slated for county sewer. Conservation Easement applies but property is approved for a large main residence and a 4 bedroom detached guest house up to 1,500 sf.

Bar Neck Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$985,000
4 Beds ⋅ 3 Baths
Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ensuite bath with a jetted tub and walk-in shower. Three additional bedrooms—one currently used as a library—share a full hall bath. An attached two-car garage provides convenient parking and storage. Residents of Tilghman on Chesapeake enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available for lease, offering residents an ideal opportunity to enjoy the waterfront lifestyle of Maryland’s Eastern Shore.

21477 Island Club Rd, Tilghman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$275,000
3 Beds ⋅ 1 Baths
This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features comfortable living spaces, a spacious yard, and the opportunity to enjoy all that Tilghman Island has to offer. Whether you're looking for a primary residence, vacation retreat, or investment opportunity, this home provides the perfect setting to experience Maryland's Chesapeake Bay lifestyle. Currently priced significantly under current appraised value!!!

21647 Camper Cir, Tilghman

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$209,700
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: admin@mdreoconnection.com
$1,250,000
4 Beds ⋅ 3 Baths
Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.

5480 Windward Dr, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$799,999
Here's your chance to own a full service waterfront restaurant and a piece of Tilghman Island history. This property has operated as a restaurant for almost 90 years. Located on Knapps Narrows, Gina's at the Bridge, is literally right next to one of the busiest drawbridges in the country. Bridge openings are by "demand of the boat" waterfront diners have many opportunities to see a wide variety of boats and watercraft coming and going. There is a full service bar inside. Indoor dining has 3 separate areas. Upstairs is an area for private dinners or small gatherings and opens to an outside deck with views of the Chesapeake Bay. Outside dining along Knapps Narrows seats about 80 people. There is also an outdoor Tiki Bar. This restaurant is turnkey. All restaurant equipment, tables, chairs, artwork etc. convey. Price includes real estate and restaurant business.

6136 Tilghman Island Rd, Tilghman

Listing courtesy of Tilghman Island Realty Inc. Contact:

$410,000
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: 4107149166
$925,000
4 Beds ⋅ 3 Baths
*INCOME PRODUCING* Tucked away in the charming Fairbank community on Tilghman Island a delightful waterfront home captures the very best of Eastern Shore living. Overlooking the serene waters of Blackwalnut Cove with approximately 3’ MLW, the property blends classic cottage character with thoughtful modern enhancements. The original portion of the home reflects its roots as a cozy summer cottage, complete with a charming screened porch perfect for enjoying warm breezes and waterfront views. A connected wing was elevated 10 feet and now features a spacious two-car garage on the main level, offering abundant storage for boats, kayaks, and gear. The rear wing provides exceptional versatility with a private studio apartment—currently a licensed B&B with its own entrance—ideal for guests, rental income, or multigenerational living. Inside the main home, a wood-burning fireplace invites you to curl up on cool days and evenings, while the screened porch becomes the heart of the home during warmer months. With 4 bedrooms and 3 baths, this property offers comfort, flexibility, and the relaxed coastal lifestyle that defines the Eastern Shore. Appointment-only showings. Do not enter the property without an appointment.

4938 Fairbank Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$1,200,000
3 Beds ⋅ 3 Baths
Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. The possibilities are endless....... Vacation Rental, 24 brand new slips, typically rent from 175.00-225.00 monthly. Develop a new fishing center, crabbing tours, sunsets cruises. Let's see what you can dream up??

21441 Dogwood Cove Rd, Tilghman

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

$2,395,000
7 Beds ⋅ 6 Baths
"Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home with natural light while framing endless Bay views, spectacular sunrises, and unforgettable sunsets. The fully renovated interior includes a redesigned chef's kitchen, spa-inspired baths, new windows and sliding doors, updated trim and fireplace features, and extensive system upgrades throughout. Exceptional waterfront amenities include expansive Trex decking, deep-water dockage, a heated indoor pool and spa pavilion, and seamless indoor-outdoor living designed for entertaining and year-round enjoyment. Major capital improvements include new HVAC systems, roof replacement, hot water heater, air purification system, decking, windows, doors, and more, offering true turnkey peace of mind. Beyond its appeal as a private waterfront retreat, "Tranquil Waters" has enjoyed a Successfull Luxury Vacation Rental history, creating an appealing opportunity for buyers seeking both lifestyle and INVESTMENT POTENTIAL. Equally suited as a luxury primary residence, waterfront getaway, or private retreat, "Tranquil Waters" delivers the ultimate Eastern Shore lifestyle: water, light, privacy, and complete escape.

21642 Chicken Point Rd, Tilghman

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

$1,945,000
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: 4108226665
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