Recently Sold Tilghman Island, MD Homes

This beautifully renovated waterfront rancher is nestled in the quaint village of Neavitt. Perfectly sited on Duck Cove with views extending to the Creek. A newly constructed front porch with a vaulted ceiling creates a welcoming focal point—an ideal space to unwind while taking in the serene water views. Inside, the open floor plan beams with natural light and features luxury vinyl plank

Kim Crouch Ozman Benson & Mangold, LLC

Simple Pleasures & Smart Living : Tilghman Island Cottage RetreatCharming Eastern Shore Cottage with Endless PossibilitiesDiscover the perfect blend of simplicity and comfort at 5934 Tilghman Island Road, wherethoughtful upgrades meet cozy cottage charm. This delightful 2-bedroom, 1 and one half bathroom homeoffers a smartly designed living space that maximizes every corner for

John McGlannan Meredith Fine Properties

This stunning waterfront retreat sits on over 5 acres just 15 minutes from St. Michaels and is designed with flexibility in mind—perfect for year-round living, hosting guests, or simply spreading out and enjoying the Eastern Shore lifestyle. The property includes both a main residence and a fully renovated guest wing, and each features a ground-floor primary suite.The main home offers

Brad Kappel TTR Sotheby's International Realty

Welcome to this charming 3-bedroom, 2-bath home designed for easy, one-level living. Thoughtfully maintained with beautiful landscapes, this residence offers the best of comfortable, yet elegant living. The formal living room includes a wood burning fireplace prefect to enjoy a cozy winter evening and just off the back, there is a screened-in porch overlooking the beautiful gardens and mature

Monica Penwell TTR Sotheby's International Realty

Enjoy this sweet waterfront cottage on Balls Creek. Protected cove with 3+ MLW, new pier, 3 bedroom & 1 bathroom. Oversized kitchen and water-view living room! Recent upgrades. Lot is .82 acres. Vacation here until it's time to build on this lot. Budget friendly!

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

Welcome to your Eastern Shore escape! Located in the heart of Tilghman Island, this beautifully maintained 3-bedroom, 1.5-bath home combines coastal charm with thoughtful modern updates—and best of all, it offers water-privileged living with deeded right-of-way access to a nearby beach. Take in stunning bay views from the large front bay window and enjoy the ease of LVP flooring throughout. The

Adam Chubbuck Douglas Realty, LLC

Nestled on a charming corner lot in the heart of Tilghman Island, this delightful three-bedroom, one-and-a-half-bath Victorian offers timeless character and modern comfort. The home features a vibrant kitchen, beautiful hardwood floors, detailed millwork arches and built-in bookshelves. The spacious primary bedroom boasts a vaulted ceiling, creating a bright and airy retreat. Relax on the

Greta Corkran Benson & Mangold, LLC

Great value - this home is in move in condition. You can start enjoying your slice of Paradise immediately. Price has been reduced on this awesome waterfront with one of the best sunset views in Tilghman. Property is in and estate and Owners are sadly ready to let this sweet property go. Welcome home to your own little bit of paradise. Three bedrooms, eat in kitchen, dining room or den,

Connie Loveland Benson & Mangold, LLC

Nestled on a little over 2.5 acres of beautifully maintained land, this charming home features a lush lawn and mature landscaping that provide a picturesque and private setting. Inside, you’ll find gleaming hardwood floors and a traditional floor plan that flows seamlessly throughout. The inviting living room is centered around a cozy wood-burning fireplace, perfect for relaxing evenings. Bright

Chuck Mangold Benson & Mangold, LLC

Local Skipjack Captain Bart Murphy and wife Florence raised their family in this sweet Island home. Conveinently located close to Dogwood Harbor and fine restaurants. Cozy oil heat was perfect after a cold day on the Bay. This house had many seafood dinners and is waiting for the next owners to enjoy Island life. There is a small attached lot that is included.

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

This former parsonage on Tilghman Island is a spacious and bright property featuring an eat-in kitchen with granite countertops, a breakfast bar, and ample cabinet space. The kitchen opens into a family room that overlooks the backyard and deck. The first floor includes an additional living area and a primary bedroom with an en-suite bathroom. Upstairs, there are two large bedrooms with vaulted

Jennifer Brown Meredith Fine Properties

CHESAPEAKE COTTAGE WITH QUAINT COZY BEACHY VIBE AT THE VERY END OF TILGHMAN ISLAND FOR YOUR FAMILY WEEKENDS.SUNRISE VIEWS ON THE WATERSIDE AND SUNSET VIEWS AT THE FRONT OF THE HOUSE, THERE IS NEVER A SHORTAGE OF SUMMER BREEZES TO ENJOY LAZY SUMMER DAYS PICKING CRABS OUTSIDE.THIS CHARMING THREE BEDROOM COTTAGE HAS 2 ADDITIONAL BUILDINGS ( 12X20 AND 9X19 ) FOR STORAGE OF KAYAKS, OUTDOOR GAMES ,

Cornelia Heckenbach Long & Foster Real Estate, Inc.

Welcome to your private waterfront retreat in charming Tilghman Island on over 5 acres of beautifully maintained property. The huge wraparound water views and broad open skies are equally inspiring. Uniquely situated at the base of the Island, this southern facing home looks across the mouth of the Choptank River and down the Chesapeake and for miles and miles. Find your tranquility in this

Debra Crouch Benson & Mangold, LLC

Exquisite Waterfront Estate in Neavitt, Maryland just minutes from historic St. Michaels.Welcome to a rare opportunity to own a truly exceptional waterfront estate in the heart of Maryland’s Eastern Shore. Nestled on over 14 pristine acres, this magnificent property boasts 7 spacious bedrooms, 5 full bathrooms, and 2 powder rooms, offering luxurious comfort for both everyday living and

Klaus Breitsameter RE/MAX Realty Group

This unique property is nestled in a setting of mature trees and lush landscaping that gives it privacy from the main road. The original two-story, three room house’s first owner was probably a waterman and there are views of Dogwood Harbor from the rear of the property. The house dates from the early 1900’s and has undergone extensive renovations through the years, without compromising its

Angela Simonelli Compass

Discover Your Slice of Paradise on Tilghman IslandWelcome to this charming retreat just a stone's throw from the shimmering waters of the Chesapeake Bay. This lovingly maintained home offers the perfect blend of cozy comfort and untapped potential. Step inside to find gleaming hardwood floors and an abundance of natural light throughout the first floor. The efficient galley kitchen flows

John McGlannan Meredith Fine Properties

This single-story rancher, located on lots #4 and #5, encompasses roughly half an acre in Tilghman, just before the island and the bridge. The property boasts a newly replaced roof, fresh interior paint, and a deck that has been pressure washed and repainted. Additionally, the two front windows have been recently installed. The removal of carpets has been completed to reveal the stunning hardwood

Stacie Luhrman Benson & Mangold, LLC

Nestled in the water-oriented community of the Tilghman Beach community this charming and updated rancher offers one-level living with modern updates. Pride of ownership shows throughout the home. The living room features a wood-burning stove and leads to the updated kitchen which boasts white cabinetry, butcher block countertops, stainless steel appliances, a pantry and a dining area, with

Kim Crouch Ozman Benson & Mangold, LLC

Welcome to 6611 Holly Woods Rd in Sherwood, MD – Situated on a serene 2-acre wooded lot, this beautifully updated 3-bedroom, 2-bath ranch-style home offers the perfect blend of modern convenience and natural charm. Located in the desirable Deep Harbour Farm community, it provides a private retreat with close access to the Chesapeake Bay’s treasures. Key Features: Prime Location: Just 8 minutes

Julie Stevenson Shore Living Real Estate

Incredible Waterfront Property Near St. Michaels - A Must-See Gem! Welcome to your dream waterfront oasis, nestled on the sought after Cooper Point Road, just seven minutes from the heart of charming St. Michaels. This remarkable property boasts a prime location on the deep, tranquil waters of Caulk Cove, offering breathtaking sunset views that will leave you speechless.Featuring three

Kathleen Coale Benson & Mangold, LLC

This offering provides a perfectly lovely waterfront setting on “Baby Owl Cove” off Broad Creek in a prime area of Bozman. The1.6 acre private parcel is improved by a 4 bedroom, 2 bath cottage with character, that dates to the 1970’s -- a good candidate for refurbishment/renovation or as a footprint for a replacement home. There is a floor plan in the documents section. Heating & cooling to

Anna Larkin Benson & Mangold, LLC

This is a must see Pristine Home in the sought after water front community of Tilghman On Chesapeake. This home boasts 3 bedrooms, 2 1/2 baths, Gourmet Kitchen and beautiful water views. Even though this home was once the model home for the community the owners have made many upgrades in excess of $100k. Community has a marina (boat slip not included- separate fee), waterfront pool, meeting

Cheri Bruce-Phipps TTR Sotheby's International Realty

A gracious front porch welcomes you to this elegant easy living home with a bright, open feel and split floor plan. Custom built by West and Callahan on a “Larry James” design the quality of materials and finishes is evident. You will admire the beautiful wood floors, generous windows and vaulted ceilings defining the Great Room with its built-in cabinets flanking the wood-burning fireplace:

Anna Larkin Benson & Mangold, LLC

The charming home in Neavitt, dating back to circa 1900, has been meticulously maintained and thoughtfully expanded over the years. Located in the picturesque waterfront Village of Neavitt, it offers a blend of historic charm and modern comfort.Key features of the property include:Location: Situated just 10 miles from St. Michaels, the home enjoys a prime location with water views from

Wink Cowee Benson & Mangold, LLC

Welcome to your coastal oasis in the sought-after water access community of Deep Harbor Farms! This charming 2-bedroom, 2-bathroom cottage is nestled within a premier boating community on Dun Cove, offering convenient dockage and mooring options right at your doorstep. Set on a sprawling 6+ acres, the property boasts sweeping panoramic views of Back Creek and the Bay, providing an ever-changing

Laura Anderson Coldwell Banker Realty

From the moment you step into this custom built home, endless water views will greet you. Open and spacious, with cathedral ceilings in the great room, the rooms are light-filled and airy. Bask in the sun on the 54' deck, or have lunch on the screened porch - so beautiful. There is a large primary suite on the first floor with updated bath as well as one upstairs, so take your pick. The great

Debra Crouch Benson & Mangold, LLC

Whether seeking a peaceful residence or a weekend getaway, this home offers the ultimate waterfront lifestyle. Western facing with stunning year-round sunsets over Harris Creek, this home features 4 bedrooms and 3 full bathrooms, perfect for family and guests. The property is set on over 2 private acres with expansive views of Harris Creek, a protected Oyster Sanctuary and fabulous boating and

Jennifer Gregorski Washington Fine Properties

Escape to the charm of Tilghman Island. This home, with 1364 square feet of living space, offers the "just right" blend of comfort, style and convenience. Inside you'll find a first floor bedroom, a formal dining room complete with bay window, built-ins for all your treasures, and a wood stove for chilly evenings, and a welcoming living room. The country kitchen offers breakfast nook/table space

Mary Haddaway Benson & Mangold, LLC

Centrally located in the heart of Tilghman Island this recently renovated farmhouse boasts 3-bedrooms, 1.5-baths and an abundance of natural light. The kitchen offers white cabinets, quartz counters, tile backsplash, new stainless steel appliances & a breakfast nook. A separate dining room flows into the spacious living room with a fireplace. Updated baths, new flooring & fresh paint throughout

Kim Crouch Ozman Benson & Mangold, LLC

Just reduced! Nestled on North Tilghman Island, this meticulously maintained 1950s waterman's cottage is a timeless gem. With 3-4 bedrooms, the first floor boasts a welcoming living room, kitchen, breakfast area, separate dining room, sunroom with a fireplace, 2-bedrooms and a full bath. Original hardwood floors add character, while the second floor offers 1-2 bedrooms and a full bath while

Kim Crouch Ozman Benson & Mangold, LLC

Tilghman Island. Classic waterman's cottage. 2 bedrooms 1.5 Baths. Centrally located, walking distance to restaurants and shops. Large fenced lot with plenty of space for your boat or RV. Lots of potential .

John McGlannan Meredith Fine Properties

John McGlannan Meredith Fine Properties