Homes for Sale near Tilghman Elementary School

Experience waterfront living in the historic community of Fairbank on Tilghman Island. This home offers timeless character and sweeping views of Black Walnut Cove. Built in 1900 with later additions, you'll find multiple decks, porches, and patios, along with a unique circular staircase leading to the second-floor porch, enhancing its architectural charm. Inside, the gourmet kitchen and family

Alicia Gannon Dulin Benson & Mangold, LLC

Waterfront home situated on Back Creek in Sherwood, offering direct access to the Chesapeake Bay and Choptank Rivers. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting.

Larry Brennan TTR Sotheby's International Realty

Barely lived in totally maintenance free rancher on a 3+/- acre lot with broad water views. Freshly painted with new landscaping it is vacant and available for immediate occupancy! Main area has beautiful wood laminate flooring with carpet in all bedrooms. Bonus room to be used as an office/family room, granite counters with wine refrigerator and all nearly new appliances with utility room and

Bill Wieland Benson & Mangold, LLC

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

Cheri Bruce-Phipps TTR Sotheby's International Realty

Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

Escape to Eastern Shore Living! Welcome to this spacious 4-bedroom, 2.5-bath gem nestled in a sought-after water-access community. Enjoy an open-concept layout flooded with natural light, perfect for entertaining or relaxing. The kitchen features stainless steel appliances, while the cozy living room includes a fireplace for year-round comfort and a bedroom on the main level. Three additional

Bean Rehbein The KW Collective

Secure and Secluded Luxury Living with Bay Views & Resort-Style BackyardProperty is located in FEMA Zone X, has never had water on the property and seller is not required to have flood insuranceTucked away at the end of a private Crepe Myrtle-lined drive, this well-maintained luxury retreat offers the perfect blend of tranquility, style, and function—without the constraints of an HOA.

Danny Martin Keller Williams Flagship

Welcome to this beautiful, spacious 5-bedroom, 3 1/2-bathroom single-family home located in the sought-after Tilghman on Chesapeake community. This property offers the perfect blend of modern comfort and serene island living, featuring an open-concept floor plan with plenty of natural light and elegant finishes. Each bedroom offers ample space and comfort with the Primary Suite offering 2

Becky Wibberley Coldwell Banker Realty

Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a

Samantha Jackson Keller Williams Realty

Potential Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home on 0.84± acres presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the

Shawn Moore Meredith Fine Properties

ENJOY Stunning SUNSETS and WATER VIEWS!! Tastefully Renovated, this 3 BR, 2 BA home is perfectly situated on 1.09 peaceful Acres overlooking the tranquil Waters of Cummings Creek. Offering true ONE LEVEL living, this turnkey property has been thoughtfully UPDATED from top to bottom in 2025! Step inside to find NEW flooring, fresh paint, stylish trim and all new interior doors with new hardware.

Pamela Ackermann-Doll RE/MAX Executive

A magnificent, stately, Daffin-built, Chesapeake Bay Brick Estate exudes excellent design and craftsmanship in this 5 bedroom (suites) , 5.5 bath 6,500 sq. ft brick home that majestically sits on 21.7 acres facing the Chesapeake Bay. Excellent construction quality and design are evident throughout this magnificent estate. Geothermal system on 1st and 2nd floors; Heat Pump for the 3rd floor;

Robert Lacaze TTR Sotheby's International Realty

BEST KEPT SECRET OF THE EASTERN SHORE ! CHARMING WATERFRONT VILLAGE WITH COMMUNITY CENTER AND FABULOUS WATER ACCESS JUST 4 MILES FROM HISTORIC ST MICHAELS. THE HISTORIC STEAMBOAT LANDING IS THE VILLAGERS WATERFRONT HANG OUT. THERE IS ALSO A POPLUAR SANDY BEACH TO ENJOY THE BAY.THIS SPACIOUS SOLID HOME HAS BEEN UPDATED WITH REPLACMENT WINDOWS, NEW SIDING, HVAC. THE INTERIOR IS IN NEED OF SOME

Cornelia Heckenbach Long & Foster Real Estate, Inc.

Wonderful opportunity to acquire a delightful cottage down the street from Fairbank public dock and landing! Easy access to crabbing, sailing and the enjoyable Chesapeake Bay. Half an acre lot with huge shade trees and water views. Enjoy the stone patio with a firepit on cool breezy evenings and all of the waterfowl visitors! Over 1700 sq. ft. of living space with a first floor bedroom and bath

Bill Wieland Benson & Mangold, LLC

Just 4.9-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings

Tom Crouch Benson & Mangold, LLC

Charming farmhouse with approximately 1300 sq feet of living space on a large, picturesque lot. Perfect weekend retreat close to St. Michaels, investment property or full time residence. The second level has two bedrooms, walk-in closet, a cozy nook ideal for a home office and a recently fully renovated bathroom. First floor includes a front room suited for an office or additional full bathroom.

Brian Petzold Benson & Mangold, LLC

This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground pool and children's play

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

Robert G. Shannahan Shoreline Realty

CHARMING SHERWOOD VILLAGE WITH ITS RICH HISTORY. ONE OF THE BEST KEPT SECRETS.STEP BACK IN TIME, WONDER PAST BEAUTIFUL GARDENS UNDER SHADE TREES, GET GREETED BY THE PEACEFUL SETTING . THE COMMUNITY DOCK WITH MULTIPLE SLIPS AND FLOATING DOCK , THE KAYAK LANDING, IS A NEIGHBORHOOD HANG OUT, VERY POPULAR AT SUNSET TIME TO ENJOY GLORIOUS SUNSETS WITH WIDE OPEN VIEWS OVER HARRIS

Cornelia Heckenbach Long & Foster Real Estate, Inc.

Price Improvement!!! Please don’t enter the home. The value is in the land.

Lesley Jackson EXIT Sunshine Realty

Welcome to Tilghman Landing on the Chesapeake Bay! This unique waterview property offers an incredible opportunity, featuring two separate homes with garages with unbelievable views of the Bay!Home #1: 6020 Sunset LaneThis spacious residence offers breathtaking, unobstructed views of the Bay. It includes 3 bedrooms and 2.5 bathrooms, and showcases an open-concept main level with a living

Melissa Tippett TTR Sotheby's International Realty

First time offered in 60 years! Nestled in the heart of a charming waterfront village, this classic 3-bedroom, 1.5-bath Eastern Shore home exudes timeless appeal. With rich historic character and warm wood floors throughout, it’s ready for your personal touch to bring it back to life. Enjoy partial water views and the convenience of a county pier and kayak launch just down the street, providing

Wink Cowee Benson & Mangold, LLC

It doesn't get any better than this ! Stunning brand-new ,one-story coastal residence with a contemporary flair! As soon as you enter this magnificent home, you will be captivated by 20'+ ceilings, superb craftsmanship , an extremely well-designed open floor-plan; breathtaking water-views on Dun Cove and a luxurious yet inviting kitchen. There are a total of 3 en-suite bedrooms as well as an

Robert Lacaze TTR Sotheby's International Realty

This has an assumable VA loan! The Nottingham, (elevation Z) is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2-car garage with entry through a mudroom that leads to an expansive Great Room area that opens to the Kitchen. The Kitchen is ready for entertaining and cooking comforting meals for family and friends. An open dinette and large kitchen island offer a plethora of space for

Stacie Luhrman Benson & Mangold, LLC

This Sherwood home truly has it all—history, charm, and modern updates. Included is the Historic Sherwood Store, which served the community for more than 160 years. A detached two-bay garage adds even more room for parking, storage, or workshop space. Just around the corner, you’ll also find a public dock and kayak launch on Harris Creek, Where you can moor your boat or jump in for a swim. It

Katie Mister Keller Williams Select Realtors of Cambridge

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

Kim Crouch Ozman Benson & Mangold, LLC

Kim Crouch Ozman Benson & Mangold, LLC

This historic property known as "The Elms" was built in 1900 and used as a fishing lodge or 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

Monica Penwell TTR Sotheby's International Realty

Very private setting. Just 10 minutes south of St. Michaels. Make this into a perfect weekend get away home. Conveniently sandwiched between St. Michael's and Tilgman Island and just right off of route 33, you will find this wonderful little opportunity to create your secluded seasonal hideout where you can enjoy all the Eastern Shore has to offer. Fishing, crabbing and swimming are just the

Joseph Craig Cummings & Co. Realtors