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Tilghman Island, MD Homes for Sale

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  • 21424 Wharf Rd, Tilghman, MD 21671
    21424 Wharf Rd, Tilghman, MD 21671
    21424 Wharf Rd, Tilghman, MD 21671
    /47

    $399,000

    • 2 Beds
    • 1 Bath
    • 1,464 Sq Ft

    21424 Wharf Rd, Tilghman, MD 21671

    **WELCOME TO YOUR VERY OWN SLICE OF "MARYLAND EASTERN SHORE PARADISE”! **A RARE OFFERING! A TRUE STORYBOOK CHARMER! ABSOLUTELY ENCHANTING, UPDATED & EXPANDED CIRCA 1900 VICTORIAN FARMHOUSE LOCATED ON PREMIER STREET IN SOUGHT AFTER "HISTORIC TILGHMAN ISLAND"; A WATER & NATURE ENTHUSIASTS DELIGHT WHICH PROUDLY BOASTS THE LARGEST WORKING SKIPJACK FLEET! COZY & INVITING, YET ELEGANT &

    Agent Photo

    Angela Simonelli

    Compass

    (410) 200-0414

    21424 Wharf Rd, Tilghman, MD 21671
  • 5379 Anchor Rd, Tilghman, MD 21671
    5379 Anchor Rd, Tilghman, MD 21671
    5379 Anchor Rd, Tilghman, MD 21671
    /56

    $560,000

    • 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

    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
    • 0.3 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
  • 0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    /12

    $75,000

    • Land
    • 0.3 Acre
    • $250,000 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
  • 5440 Anchor Rd, Tilghman, MD 21671
    5440 Anchor Rd, Tilghman, MD 21671
    5440 Anchor Rd, Tilghman, MD 21671
    /32

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    5440 Anchor Rd, Tilghman, MD 21671

    TILGHMAN ISLAND: Discover your dream home in the charming, water-privileged community of Tilghman Beach. This stunning ranch-style home, built in 2018, offers modern conveniences and one-level living at its finest, perfect for those seeking a serene lifestyle by the water.Key Features:Spacious Open Floor Plan: Enjoy seamless living with a large combination living and dining area,

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 657-6713

    5440 Anchor Rd, Tilghman, MD 21671
  • 6135 Summit St, Tilghman, MD 21671
    6135 Summit St, Tilghman, MD 21671
    6135 Summit St, Tilghman, MD 21671
    /31

    $399,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    6135 Summit St, Tilghman, MD 21671

    Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 593-3451

    6135 Summit St, Tilghman, MD 21671
  • 21749 Camper Cir, Tilghman, MD 21671
    21749 Camper Cir, Tilghman, MD 21671
    21749 Camper Cir, Tilghman, MD 21671
    /25

    $295,000

    • 3 Beds
    • 1 Bath
    • 1,224 Sq Ft

    21749 Camper Cir, Tilghman, MD 21671

    A fantastic opportunity awaits at 21749 Camper Circle in Tilghman, Maryland. This home is perfect for first-time buyers or investors looking for great value at an affordable price. It features central heating and air conditioning, three spacious bedrooms, and one full bathroom. Enjoy a large sunroom with tile flooring that is conveniently located next to the kitchen. The hardwood floors

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 498-8659

    21749 Camper Cir, Tilghman, MD 21671
  • 5820 Tilghman Beach Dr, Tilghman, MD 21671
    5820 Tilghman Beach Dr, Tilghman, MD 21671
    5820 Tilghman Beach Dr, Tilghman, MD 21671
    /32

    $795,000

    • 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,

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 927-1165

    5820 Tilghman Beach Dr, 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

    $749,900

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

    4957 Bar Neck Rd, Tilghman, MD 21671

    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

    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
  • 10437 Main St, Claiborne, MD 21624
    10437 Main St, Claiborne, MD 21624
    10437 Main St, Claiborne, MD 21624
    /44

    $318,000 Open Sat 10:30AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,376 Sq Ft

    10437 Main St, Claiborne, MD 21624

    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 ROOF, NEW SIDING, HVAC. THE INTERIOR IS

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    10437 Main St, Claiborne, MD 21624
  • 0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671
    0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671
    0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671
    /4

    $3,500,000

    • Land
    • 64.88 Acres
    • $53,946 per Acre

    0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671

    Very rare opportunity to buy a truly beautiful Eastern Shore Farm. This 65 acre farm has four residential building sites. There are two ponds and nearly 4,000’ of rip-rapped shoreline. Build your dream home or compound with unobstructed views of the Chesapeake Bay and Choptank River.

    Chuck Mangold Benson & Mangold, LLC

    0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671
  • 4905 Fairbank Rd, Tilghman, MD 21671
    4905 Fairbank Rd, Tilghman, MD 21671
    4905 Fairbank Rd, Tilghman, MD 21671
    /20

    $559,000

    • 3 Beds
    • 2 Baths
    • 1,724 Sq Ft

    4905 Fairbank Rd, Tilghman, MD 21671

    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

    4905 Fairbank Rd, Tilghman, MD 21671
  • 21368 Fairbank Cir, Tilghman, MD 21671
    21368 Fairbank Cir, Tilghman, MD 21671
    21368 Fairbank Cir, Tilghman, MD 21671
    /66

    $1,150,000

    • 4 Beds
    • 3 Baths
    • 3,552 Sq Ft

    21368 Fairbank Cir, Tilghman, MD 21671

    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

    21368 Fairbank Cir, Tilghman, MD 21671
  • 6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    /64

    $1,299,000

    • 3 Beds
    • 3 Baths
    • 3,853 Sq Ft

    6670 Tilghman Island Rd, Sherwood, MD 21665

    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

    6670 Tilghman Island Rd, Sherwood, MD 21665
  • 21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    /50

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 3,040 Sq Ft

    21477 Island Club Rd, Tilghman, MD 21671

    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

    21477 Island Club Rd, Tilghman, MD 21671
  • 6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    /74

    $1,275,000

    • 3 Beds
    • 3 Baths
    • 3,232 Sq Ft

    6050 Sunset Ln, Tilghman, MD 21671

    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

    6050 Sunset Ln, Tilghman, MD 21671
  • 6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    /47

    $1,745,000

    • 6 Beds
    • 6 Baths
    • 4,397 Sq Ft

    6020 Sunset Ln, Tilghman, MD 21671

    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

    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

    $554,999

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

    5582 Trafalgar Cir, Tilghman, MD 21671

    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

    5582 Trafalgar Cir, Tilghman, MD 21671
  • 5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    /15

    $499,888 New Construction

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    5654 Trafalgar Cir, Tilghman, MD 21671

    The New Castle is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2 car garage with drop zone entry, attached to a laundry room, that leads through to the Kitchen. The Kitchen has a large amount of space, plenty of cabinets, and a pantry, making storage and organization plentiful and manageable. The well-equipped kitchen is ready for entertaining and with family and friends. The open

    Mary Ann Hammel Mary Ann Hammel

    5654 Trafalgar Cir, Tilghman, MD 21671
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /25

    $544,888 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
  • 5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    /83

    $1,200,000

    • 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
  • 6705 Tilghman Island Rd, Sherwood, MD 21665
    6705 Tilghman Island Rd, Sherwood, MD 21665
    6705 Tilghman Island Rd, Sherwood, MD 21665
    /40

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    6705 Tilghman Island Rd, Sherwood, MD 21665

    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

    6705 Tilghman Island Rd, Sherwood, MD 21665
Maryland Talbot County Tilghman Island

Real Estate & Homes for Sale in Tilghman Island, MD

Why Live in Tilghman Island

Once a 19th-century hub for oystermen and crabbers across the Chesapeake Bay, Tilghman Island is today a quaint coastal village on Maryland's Eastern Shore. Residents appreciate boating and fishing in the bay's brackish waters or enjoying drinks and ...

Learn more about living in Tilghman Island

Frequently Asked Questions

What are the most popular zip codes in Tilghman Island, MD?
The most popular zip codes in Tilghman Island, MD include 21671, 21624, 21665, 21612 and 21663.
How are the schools in Tilghman Island, MD?
Tilghman Island, MD has highly rated public and private schools. Some of the best schools in Tilghman Island based on Niche Grades are Easton High School, St. Michaels Middle/High School and Tilghman Elementary School. Browse all the schools in Tilghman Island, MD to learn more.
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