Tilghman MD Real Estate & Homes for Sale

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.

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.

Charming 2-3BR/2BA coastal cottage with tranquil water views of Black Walnut Cove and the Choptank River - ideal for easy full-time living or a relaxed weekend retreat. Beautiful hardwood floors run throughout, complementing the home's warm, welcoming character and comfortable scale. The living room, anchored by a wood-burning fireplace, offers a cozy gathering space, while the kitchen is thoughtfully designed with a large center island, wet bar, and French door access to a beautiful screened porch overlooking the cove - perfect for morning coffee, quiet afternoons, or casual evening entertaining. The primary suite is a peaceful retreat, featuring an ensuite bath, walk-in closet, and convenient laundry cubby. An adjoining second bedroom offers flexibility as a private office, sitting room, or additional sleeping space. A third bedroom and full hall bath provide comfortable accommodation for guests. Additional highlights include a garden shed and a fully conditioned she shed with heat and AC, currently used as an art studio - a versatile space for hobbies or creative pursuits. Numerous improvements include a new roof, Pella architectural windows, encapsulated crawlspace, 3-zone Mitsubishi mini-split system, reverse-osmosis water filtration, and more. This thoughtfully updated cottage offers the best of Eastern Shore living with a relaxed, waterside feel.

Historic Tilghman Island W design home circa 1890 offering classic Eastern Shore character with extensive recent updates. Four bedrooms and two fully renovated baths. Kitchen features updated granite countertops, stove, refrigerator, and dishwasher. Newer flooring and subflooring throughout. Bathrooms include designer tile floors and tiled showers. Recently replaced HVAC system. Main level includes one bedroom and one full bath. Upper level offers three bedrooms and a second full bath. Ideally located within walking distance to marinas, waterfront dining, local shops, the Tilghman Wharf development, and the Wylder Hotel. Just minutes from the Tilghman Island Narrows, providing easy access to boating, fishing, crabbing, kayaking, and Chesapeake Bay water activities. Suitable for a primary residence, second home, or potential rental property in one of the Eastern Shore's most authentic waterfront communities.

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.

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.

Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center island with bar seating, a pantry and ample cabinet space, perfect for everyday living and entertaining. The kitchen overlooks the living room, featuring a cozy gas fireplace and an open dining area with a sliding glass door, ideal for adding a future deck or patio. The primary suite is privately situated off the main living space and features two walk-in closets and a luxurious bathroom with a granite double-sink vanity, tile and glass shower and a linen closet. Two additional bedrooms and a full guest bath are located on the opposite side of the home, offering privacy for guests or family members. A separate laundry/mudroom provides convenient access to the attached two-car garage. Built by Gemcraft Homes, a highly regarded regional builder, this home provides peace of mind with a 1-year builder warranty, 2-year HVAC/plumbing/electrical coverage and a 5-year structural warranty. For a separate fee, owners can enjoy the amenities of the Tilghman on the Chesapeake waterfront clubhouse, which features a pool and recreation room with an expansive deck and balcony, perfect for hosting events or gatherings. Boat slips are also available, offering easy access to the Bay. Located just moments from local restaurants, multiple boat landings, prime fishing spots and centrally positioned for boating to St. Michaels, Kent Island, Oxford, Cambridge and Annapolis. This isn't just a home, it's a lifestyle.

PRICE IMPROVEMENT*** Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina - perfect for boating, entertaining, and leisure. Whether you're looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! NEW ROOF & FIREPLACE 2024, NEW APPLIANCES 2019

Are you looking for serenity? Tucked away at the end of a picturesque crepe myrtle-lined drive is a breath of fresh air with its peacefully remote surroundings that many people are looking for. 12 miles to St. Michaels, close to Easton and Oxford, This exceptional waterview retreat offers a rare combination of privacy, scenic beauty, and convenience. The property is overlooking Black Walnut Creek, with glimpses of the Chesapeake Bay beyond, this property delivers a true sense of escape. Whether you are seeking a full-time residence, a weekend getaway, or an income-producing short-term rental, the setting and lifestyle here are simply unmatched. Even better, there is no HOA, allowing you the freedom to fully enjoy and personalize your property. Located in FEMA Flood Zone X, with no history of water intrusion, this home provides both peace of mind and long-term value in one of the Eastern Shore's most desirable destinations. Inside, thoughtful design meets everyday comfort. The home welcomes you through a gracious front foyer, while a secondary mudroom entrance, complete with laundry, utility sink, storage, and a full bath, offers the perfect transition after days spent poolside or on the water. The main level is designed for both relaxed living and effortless entertaining, featuring multiple inviting spaces including a refined parlor with custom built-ins and a warm, welcoming family room anchored by a wood-burning fireplace that extends to the second level for added efficiency. Sliding doors open seamlessly to the outdoor living areas, creating an easy indoor-outdoor flow. At the heart of the home, the kitchen is both functional and stylish, featuring granite countertops, light wood cabinetry, stainless steel appliances, and a breakfast bar. Just beyond, a spacious deck and patio overlook the in-ground pool, offering an idyllic setting for summer gatherings or quiet evenings under the stars. A formal dining room provides views of the front grounds, perfect for more intimate occasions. Upstairs, three well-appointed bedrooms include a spacious primary suite complete with a walk-in closet, additional linen storage, and a private en-suite bath featuring a jetted soaking tub and double vanity. A versatile bonus room offers flexibility as a fourth bedroom, home office, or creative space. Outdoors, the property truly shines. Multiple seating areas surround the in-ground pool, all framed by tranquil water views and natural landscaping. Both attached and detached garages provide abundant space for vehicles, hobbies, and storage, while the fully concreted crawlspace adds even more functionality. For those drawn to life on the water, several nearby public boat launches and a convenient kayak launch just down the street make it easy to explore the surrounding waterways and the Chesapeake Bay. Additional features include dual security systems, fire and carbon monoxide detection, and a custom exterior camera system, offering comfort and peace of mind. This is more than a home. It is a private Eastern Shore retreat designed for those who value space, serenity, and connection to the water. Schedule your private showing and experience it for yourself.