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Homes for Sale in 21671

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  • 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
  • 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
  • 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
  • 21749 Camper Cir, Tilghman, MD 21671
    21749 Camper Cir, Tilghman, MD 21671
    21749 Camper Cir, Tilghman, MD 21671
    /25

    $275,000

    • 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) 936-4361

    21749 Camper Cir, 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

    $699,900

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

    4957 Bar Neck Rd, Tilghman, MD 21671

    Private Retreat with Pool, Bay Views & No HOA — Flood Zone X This is a rare opportunity to own a private property with water views, outdoor living, and no HOA restrictions. The sellers are ready for their next chapter and welcome serious inquiries Tucked at the end of a private Crepe Myrtle–lined drive, this well-maintained home offers rare privacy, water views, and the freedom of no HOA, all

    Danny Martin Keller Williams Flagship

    4957 Bar Neck Rd, 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
  • 6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    /74

    $1,175,000

    • 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
  • 21560 Chicken Point Rd, Tilghman, MD 21671
    21560 Chicken Point Rd, Tilghman, MD 21671
    21560 Chicken Point Rd, Tilghman, MD 21671
    /25

    $895,000

    • 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
  • 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
  • 21552 Chicken Point Rd, Tilghman, MD 21671
    21552 Chicken Point Rd, Tilghman, MD 21671
    21552 Chicken Point Rd, Tilghman, MD 21671
    /14

    $995,000

    • 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 master 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
  • 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
  • 5582 Trafalgar Cir, Tilghman, MD 21671
    5582 Trafalgar Cir, Tilghman, MD 21671
    5582 Trafalgar Cir, Tilghman, MD 21671
    /18

    $525,000

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

    5582 Trafalgar Cir, Tilghman, MD 21671

    Welcome to 5582 Trafalgar Cir (truh-FAL-gar), a beautifully maintained single-level, 3-bedroom, 2.5-bath home located in the desirable Tilghman on Chesapeake community. Built in 2023 and offering 2,110 square feet of thoughtfully designed living space, this home has been lived in for only about a year and truly shows better than new. The seller’s meticulous care and attention to detail have

    BJ Kilby Eastern Shore Real Estate, LLC

    5582 Trafalgar Cir, 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

    $2,499,000

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

    21485 Island Club Rd, Tilghman, MD 21671

    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 framed by expansive windows that fill the home with ethereal lighting.

    Alicia Gannon Dulin Benson & Mangold, LLC

    21485 Island Club Rd, Tilghman, MD 21671
  • 21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    /32

    $549,000

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

    21486 Mission Rd, Tilghman, MD 21671

    This historic property known as "The Elms" was built in 1900 and originally used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water and consists of three buildings which are: The original main building, the detached garage and a shed/storage building. The buildings hold virtually no value unless and extensive historic renovation were completed, but

    Monica Penwell TTR Sotheby's International Realty

    21486 Mission 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
  • 21524 Chicken Point Rd, Tilghman, MD 21671
    21524 Chicken Point Rd, Tilghman, MD 21671
    21524 Chicken Point Rd, Tilghman, MD 21671
    /41

    $369,000

    • 4 Beds
    • 2 Baths
    • 1,761 Sq Ft

    21524 Chicken Point Rd, Tilghman, MD 21671

    Historic Tilghman Island “W” design home circa 1890 offering classic Eastern Shore character with extensive recent updates. Four bedrooms and two fully renovated baths. Kitchen features updated granite countertops, stove, refrigerator, and dishwasher. Newer flooring and subflooring throughout. Bathrooms include designer tile floors and tiled showers. Recently replaced HVAC system. Main level

    Debbie Lipscomb Benson & Mangold, LLC

    21524 Chicken Point 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
    /13

    $950,000

    • 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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