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.
Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor master suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor with 4 additional guest bedrooms and bath. This renovated home also has a separate 3 bay garage with a 2-bedroom 2-bath water view apartment with a nice open living and dining area and total square footage of 768. The main house has an attached 1 bedroom 1 bath in-law suite. Great space for your guests or potential for a vacation rental. A nice wide-open lawn leads you to the dock with 7 boat slips. Right on the Knapps Narrows. Tilghman is the perfect place to start making your Eastern Shore Memories. New pictures to come...
Renovated waterfront living with room for your fleet! Extensively renovated cape cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive tin roof and owned solar energy system. Situated along protected waterfront with long water views and five boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.
The opportunities abound for this waterfront home overlooking the Knapps Narrows. Formally, Maynard Lowery's boat building business, this residentially zoned, single-family home comes with 5 boat slips and unlimited possibilities. Can be easily expanded up to 6 bedrooms and 4 baths. The first level would make an ideal hobby area or additional living area. Handicap Accessible with elevator. Commercial potential.
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.
TILGHMAN ISLAND. Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite countertops, stylish modern appliances, a large center island, and an oversized walk-in pantry—perfect for both everyday cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, where a stunning gas fireplace creates a warm and inviting atmosphere for daily living and special gatherings. Upstairs, you will find a thoughtfully designed layout offering comfort and privacy. The expansive primary suite is a true retreat, complete with two separate walk-in closets and a luxurious en-suite bath. An additional generously sized ensuite bedroom provides excellent flexibility for family or guests, while the remaining bedrooms offer ample space and versatility for a home office, gym, or guest accommodations. Situated in the tranquil Tilghman on Chesapeake community, residents enjoy access to exceptional amenities, including a community pool, clubhouse, and deep-water boat slips available through the HOA. Ideally located near the Chesapeake Bay and surrounding tributaries, this home offers unparalleled access to boating, deep-water fishing, crabbing, and scenic coastal adventures. Miles of open bike trails and the peaceful charm of Tilghman Island complete the experience, making this property the perfect blend of luxury, comfort, and true Bay living.
Looking for a home with a private setting, water views, a pool, and no HOA — all within easy reach of the charm and activities of St. Michaels and Easton? Interested in a quiet home retreat or a short term rental?Look no further! Enjoy privacy, water views, and the freedom of no HOA at this tucked-away property located at the end of a Crepe Myrtle–lined drive. Surrounded by mature trees and overlooking Black Walnut Creek with glimpses of the Chesapeake Bay, this home offers a peaceful setting that feels like a private retreat while still being close to the vibrant waterfront towns of St. Michaels and Easton, known for their dining, shopping, boating, and year-round events. Located in FEMA Flood Zone X (no flood insurance required and no history of water intrusion), the property also offers excellent potential as a weekend getaway, second home, or short-term rental in one of the Eastern Shore’s most desirable destinations. Inside, the home offers two convenient entry points — a welcoming front foyer and a mudroom/laundry entrance with utility sink, storage, and access to a full bath, perfect after time spent by the pool or on the water. The main level features multiple living spaces including a parlor with built-in shelving and a cozy family room with a wood-burning fireplace. The fireplace stack extends to the second floor, providing efficient supplemental heating. Sliding doors lead directly to the backyard and outdoor living areas. The open kitchen includes granite countertops, light wood cabinetry, stainless steel appliances, and a breakfast bar. From here, step outside to the deck and patio overlooking the in-ground pool — an ideal setting for summer gatherings and relaxing evenings. A separate dining room overlooks the front yard. Upstairs are three bedrooms, including a spacious primary suite with walk-in closet, linen storage, and an en-suite bath with jetted soaking tub and double vanity. An additional flexible room can function as a fourth bedroom, home office, or hobby space. A long hallway provides additional storage. The backyard is designed for enjoying the outdoors, with multiple seating areas surrounding the in-ground pool and water views beyond. Both attached and detached garages provide ample parking and storage, and the fully concreted crawlspace adds additional functional space. Outdoor enthusiasts will appreciate the nearby water access, including multiple public boat launches and a kayak launch just down the street, making it easy to explore the surrounding creeks and the Chesapeake Bay. The home is equipped with two burglar alarms, fire and carbon monoxide detectors, and a custom exterior camera system for added peace of mind. The sellers are ready for their next chapter and welcome serious buyers. Schedule your showing and come experience this unique Eastern Shore property for yourself.
*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**
This historic property known as "The Elms" was built in 1900 and used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water. The buildings hold virtually no value unless and extensive historic renovation were completed. Tilghman is an historic waterfront town that features a waterman's museum, marina, many restaurants, established neighborhoods/communities such as Tilghman on the Chesapeake, Fairbanks, and Black Walnut Point. This historic property offers many opportunities. Property being sold "As-Is."
Tilghman is located in Maryland. Tilghman 21671 is less family-centric than the surrounding county with 13.2% of the households containing married families with children. The county average for households married with children is 22.67%.
