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Tilghman Island Homes for Sale

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  • 0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    /12

    $89,000

    • Land
    • 0.30 Acre
    • $296,667 per Acre

    0 Sinclair Rd, Tilghman Island, MD 21671

    Sinclair Ave. Tilghman Island. Clear level building lot with public sewer. This lot is ready for you to make your dream of island life come true.Enjoy the best sunsets at the end of the street at Sinclair Community Park .

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 297-6839

    0 Sinclair Rd, Tilghman Island, MD 21671
  • 5820 Tilghman Beach Dr, Tilghman, MD 21671
    5820 Tilghman Beach Dr, Tilghman, MD 21671
    5820 Tilghman Beach Dr, Tilghman, MD 21671
    /31

    $889,000

    • 2 Beds
    • 1 Bath
    • 1,776 Sq Ft

    5820 Tilghman Beach Dr, Tilghman, MD 21671

    Welcome to 5820 Tilghman Beach Drive. Come experience the most beautiful sunsets the Chesapeake Bay has to offer. Centrally located on Tilghman Island this little slice of paradise is ready for its new owners to make their dream of waterfront living come true.Home offers two bedrooms and one full bath, hardwood floors, recently remodeled kitchen, encapsuled crawl space, Central heat and air, two

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 927-1165

    5820 Tilghman Beach Dr, Tilghman, MD 21671
  • 5934 Tilghman Island Rd, Tilghman, MD 21671
    5934 Tilghman Island Rd, Tilghman, MD 21671
    5934 Tilghman Island Rd, Tilghman, MD 21671
    /41

    $365,000

    • 2 Beds
    • 1.5 Baths
    • 892 Sq Ft

    5934 Tilghman Island Rd, Tilghman, MD 21671

    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 comfortable

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 222-3534

    5934 Tilghman Island Rd, Tilghman, MD 21671
  • 5379 Anchor Rd, Tilghman, MD 21671
    5379 Anchor Rd, Tilghman, MD 21671
    5379 Anchor Rd, Tilghman, MD 21671
    /56

    $610,000

    • 2 Beds
    • 2.5 Baths
    • 1,232 Sq Ft

    5379 Anchor Rd, Tilghman, MD 21671

    Bay Breezes & Beautiful Views: Your Tilghman Island HavenWaterview Living with Room to Breathe on Maryland's Eastern ShoreStep into the good life at 5379 Anchor Road, where Chesapeake Bay magic meets everydaycomfort. This charming home in Tilghman's friendly beach neighborhood sits just ashort stroll from the community beach where neighbors gather and memories are made.Picture yourself unwinding

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 206-6165

    5379 Anchor Rd, Tilghman, MD 21671
  • 21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    /10

    $80,000

    • Land
    • 0.30 Acre
    • $266,667 per Acre

    21472 Willey Rd, Tilghman, MD 21671

    Tilghman Island. Clear level building lot with public sewer available. The perfect spot for your new vacation / retirement home. Excellent opportunity to make your island dream come true.

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 382-8747

    21472 Willey Rd, Tilghman, MD 21671
  • 4957 Bar Neck Rd, Tilghman, MD 21671
    4957 Bar Neck Rd, Tilghman, MD 21671
    4957 Bar Neck Rd, Tilghman, MD 21671
    /45

    $895,000

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft

    4957 Bar Neck Rd, Tilghman, MD 21671

    Don't miss out on this beautifully landscaped yard with a deck and pool, perfect for entertaining and enjoying the serene water views. This gorgeous two-story traditional home features three bedrooms and three baths, offering the perfect location to enjoy the picturesque views of Black Walnut Creek and the Chesapeake Bay.The current owners have meticulously maintained the property and spent a

    Lori Neske Coldwell Banker Realty

    4957 Bar Neck Rd, Tilghman, MD 21671
  • 21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    /35

    $699,000

    • 9 Beds
    • 2.5 Baths
    • 5,389 Sq Ft

    21486 Mission Rd, Tilghman, MD 21671

    History:"The Elms" is located on the Northeast corner of Mission Road and Route 33 in the village of Tilghman on Tilghman Island, Talbot County, MD. The house faces west, with the gable oriented on a north/south axis. Built around 1893. The Elms is clad in weatherboard and supported by a brick pier foundation. The roof of this two story frame home is covered in asphalt shingles. The five bay

    Daphne Cawley TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • 5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    /83

    $1,750,000

    • 5 Beds
    • 2.5 Baths
    • 4,214 Sq Ft

    5520 Leeward Ln, Tilghman, MD 21671

    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

    5520 Leeward Ln, Tilghman, MD 21671
  • 6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    /50

    $2,795,000

    • 7 Beds
    • 7 Baths
    • 6,377 Sq Ft

    6020 Sunset Ln, Tilghman, MD 21671

    Welcome to Tilghman Landing on the Chesapeake Bay! This unique waterfront property offers an incredible opportunity, featuring three separate homes, two of which include garages, as well as a charming crab shack and private dock, all situated on .625 acres of Chesapeake Bay shoreline.Home #1: 6020 Sunset LaneThis spacious residence offers breathtaking, unobstructed views of the Bay. It includes 3

    Melissa Tippett TTR Sotheby's International Realty

    6020 Sunset Ln, Tilghman, MD 21671
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /62

    $600,000

    • 5 Beds
    • 3.5 Baths
    • 3,404 Sq Ft

    5559 Trafalgar Cir, Tilghman, MD 21671

    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

    5559 Trafalgar Cir, Tilghman, MD 21671
  • 5582 Trafalgar Cir, Tilghman, MD 21671
    5582 Trafalgar Cir, Tilghman, MD 21671
    5582 Trafalgar Cir, Tilghman, MD 21671
    /58

    $560,000 Open Sat 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,110 Sq Ft

    5582 Trafalgar Cir, Tilghman, MD 21671

    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 informal dining. You can take

    Stacie Luhrman Benson & Mangold, LLC

    5582 Trafalgar Cir, Tilghman, MD 21671
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /25

    $556,990 New Construction

    • 3 Beds
    • 2 Baths
    • 2,068 Sq Ft

    5648 Trafalgar Cir, Tilghman, MD 21671

    THIS HOME IS UNDER CONSTRUCTION!Welcome to Sussex, the epitome of modern rancher living! This single-level floor plan has captured the hearts of many, and it's not hard to see why. With stunning curb appeal and thoughtfully designed features and finishes, the Sussex offers versatility to suit any modern lifestyle. Step into an open-concept floor plan that seamlessly connects the Kitchen,

    Mary Ann Hammel Mary Ann Hammel

    5648 Trafalgar Cir, Tilghman, MD 21671
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