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Homes for Sale in 21671

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  • 5698 Leeward Ln, Tilghman, MD 21671
    5698 Leeward Ln, Tilghman, MD 21671
    5698 Leeward Ln, Tilghman, MD 21671
    /41

    $1,995,000

    • 5 Beds
    • 3.5 Baths
    • 3,906 Sq Ft

    5698 Leeward Ln, Tilghman, MD 21671

    Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat in Tilghman Island. Thoughtfully redesigned and updated in 2023, this exceptional property seamlessly blends refined coastal living with the tranquility and natural beauty of its extraordinary waterfront setting.Inside, the light-filled great room is the heart of the home, with

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 888-0416

    5698 Leeward Ln, Tilghman, MD 21671
  • 5933 Tilghman Island Rd, Tilghman, MD 21671
    5933 Tilghman Island Rd, Tilghman, MD 21671
    5933 Tilghman Island Rd, Tilghman, MD 21671
    /35

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    5933 Tilghman Island Rd, Tilghman, MD 21671

    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

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 242-9472

    5933 Tilghman Island Rd, Tilghman, MD 21671
  • 0 Sinclair Ave, Tilghman Island, MD 21671
    0 Sinclair Ave, Tilghman Island, MD 21671
    0 Sinclair Ave, Tilghman Island, MD 21671
    /10

    $75,000

    • Land
    • 13,068 Sq Ft
    • $250,000 per Acre

    0 Sinclair Ave, Tilghman Island, MD 21671

    Build your dream home on beautiful Tilghman Island! This ideally located lot is within walkingdistance of Sinclair Community Park, local marinas, charming shops, and popular waterfrontrestaurants. Stroll to the end of your street to enjoy stunning Chesapeake Bay sunsets from thepark’s scenic shoreline.Tilghman Island is a beloved Eastern Shore destination known for its rich

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 863-3363

    0 Sinclair Ave, Tilghman Island, MD 21671
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /75

    $569,000

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

    5559 Trafalgar Cir, Tilghman, MD 21671

    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

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 834-0959

    5559 Trafalgar Cir, Tilghman, MD 21671
  • 21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    /10

    $72,500

    $8K PRICE DROP
    • Land
    • 13,068 Sq Ft
    • $241,667 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 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
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /43

    $544,888

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

    5648 Trafalgar Cir, Tilghman, MD 21671

    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

    5648 Trafalgar Cir, Tilghman, MD 21671
  • 21642 Chicken Point Rd, Tilghman, MD 21671
    21642 Chicken Point Rd, Tilghman, MD 21671
    21642 Chicken Point Rd, Tilghman, MD 21671
    /63

    $2,695,000

    • 7 Beds
    • 5.5 Baths
    • 4,151 Sq Ft

    21642 Chicken Point Rd, Tilghman, MD 21671

    Tranquil Waters” is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21642 Chicken Point Rd, Tilghman, MD 21671
  • 21560 Chicken Point Rd, Tilghman, MD 21671
    21560 Chicken Point Rd, Tilghman, MD 21671
    21560 Chicken Point Rd, Tilghman, MD 21671
    /78

    $870,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,314 Sq Ft

    21560 Chicken Point Rd, Tilghman, MD 21671

    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

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21560 Chicken Point Rd, Tilghman, MD 21671
  • 21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    /83

    $1,950,000

    • 5 Beds
    • 4.5 Baths
    • 4,303 Sq Ft

    21485 Island Club Rd, Tilghman, MD 21671

    Back on the market due to Buyers unable to fulfill home sale contingency- Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views

    Alicia Gannon Dulin Benson & Mangold, LLC

    21485 Island Club Rd, Tilghman, MD 21671
  • 21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    /50

    $1,150,000

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

    21477 Island Club Rd, Tilghman, MD 21671

    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

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    21477 Island Club Rd, Tilghman, MD 21671
  • 21552 Chicken Point Rd, Tilghman, MD 21671
    21552 Chicken Point Rd, Tilghman, MD 21671
    21552 Chicken Point Rd, Tilghman, MD 21671
    /77

    $970,000

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,655 Sq Ft

    21552 Chicken Point Rd, Tilghman, MD 21671

    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 primary 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

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21552 Chicken Point Rd, Tilghman, MD 21671
  • 5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    /49

    $499,888

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

    5654 Trafalgar Cir, Tilghman, MD 21671

    Kim Crouch Ozman Benson & Mangold, LLC

    5654 Trafalgar Cir, Tilghman, MD 21671
  • 21530 Coopertown Rd, Tilghman, MD 21671
    21530 Coopertown Rd, Tilghman, MD 21671
    21530 Coopertown Rd, Tilghman, MD 21671
    /23

    $279,000

    • 3 Beds
    • 1 Bath
    • 996 Sq Ft

    21530 Coopertown Rd, Tilghman, MD 21671

    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

    Kim Crouch Ozman Benson & Mangold, LLC

    21530 Coopertown Rd, Tilghman, MD 21671
  • 21524 Chicken Point Rd, Tilghman, MD 21671
    21524 Chicken Point Rd, Tilghman, MD 21671
    21524 Chicken Point Rd, Tilghman, MD 21671
    /41

    $349,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,761 Sq Ft

    21524 Chicken Point Rd, Tilghman, MD 21671

    Move-in ready on Tilghman Island — close to marinas, waterfront dining, and the Wylder Hotel. This fully renovated 4BR/2BA home blends Eastern Shore location with completely updated kitchen, baths, flooring, and HVAC. Nothing to do but enjoy the Chesapeake.

    Debbie Lipscomb Benson & Mangold, LLC

    21524 Chicken Point Rd, Tilghman, MD 21671
  • 21441 Dogwood Cove Rd, Tilghman, MD 21671
    21441 Dogwood Cove Rd, Tilghman, MD 21671
    21441 Dogwood Cove Rd, Tilghman, MD 21671
    /14

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,477 Sq Ft

    21441 Dogwood Cove Rd, Tilghman, MD 21671

    Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. More info and photos to follow.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21441 Dogwood Cove Rd, Tilghman, MD 21671
  • 21572 Chicken Point Rd, Tilghman Island, MD 21671
    21572 Chicken Point Rd, Tilghman Island, MD 21671
    21572 Chicken Point Rd, Tilghman Island, MD 21671
    /72

    $925,000

    $25K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,729 Sq Ft

    21572 Chicken Point Rd, Tilghman Island, MD 21671

    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.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21572 Chicken Point Rd, Tilghman Island, MD 21671
Maryland Talbot County Tilghman 21671

Real Estate & Homes for Sale in 21671

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