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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

    5698 Leeward Ln, 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

    21472 Willey Rd, Tilghman, MD 21671
  • 21406 Dogwood Cove Rd, Tilghman, MD 21671
    21406 Dogwood Cove Rd, Tilghman, MD 21671
    21406 Dogwood Cove Rd, Tilghman, MD 21671
    /68

    $410,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    21406 Dogwood Cove Rd, Tilghman, MD 21671

    Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    21406 Dogwood Cove 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

    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

    $68,500

    $7K PRICE DROP
    • Land
    • 13,068 Sq Ft
    • $228,333 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

    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

    $564,000

    $5K PRICE DROP
    • 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

    5559 Trafalgar Cir, Tilghman, MD 21671
  • 4938 Fairbank Rd, Tilghman, MD 21671
    4938 Fairbank Rd, Tilghman, MD 21671
    4938 Fairbank Rd, Tilghman, MD 21671
    /45

    $950,000

    $55K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 2,850 Sq Ft

    4938 Fairbank Rd, Tilghman, MD 21671

    *INCOME PRODUCING* Tucked away in the charming Fairbank community on Tilghman Island, this delightful waterfront home captures the very best of Eastern Shore living. Overlooking the serene waters of Blackwalnut Cove with approximately 3’ MLW, the property blends classic cottage character with thoughtful modern enhancements. The original portion of the home reflects its roots as a cozy summer

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    4938 Fairbank 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
  • 21647 Camper Cir, Tilghman, MD 21671
    21647 Camper Cir, Tilghman, MD 21671
    21647 Camper Cir, Tilghman, MD 21671
    /25

    $295,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 1 Bath
    • 1,262 Sq Ft

    21647 Camper Cir, Tilghman, MD 21671

    Welcome to 21647 Camper Circle in the charming waterfront community of Tilghman Island. This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features

    Heather Brummell Keller Williams Realty

    21647 Camper Cir, Tilghman, MD 21671
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /43

    $529,888

    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
    /144

    $2,475,000

    $220K PRICE DROP
    • 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

    $845,000

    $50K 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
  • 5480 Windward Dr, Tilghman, MD 21671
    5480 Windward Dr, Tilghman, MD 21671
    5480 Windward Dr, Tilghman, MD 21671
    /59

    $1,250,000

    • 4 Beds
    • 3 Baths
    • 1,936 Sq Ft

    5480 Windward Dr, Tilghman, MD 21671

    Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting

    Kim Crouch Ozman Benson & Mangold, LLC

    5480 Windward Dr, 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
  • 4869 Bar Neck Rd, Tilghman, MD 21671
    4869 Bar Neck Rd, Tilghman, MD 21671
    4869 Bar Neck Rd, Tilghman, MD 21671
    /22

    $229,700

    • 2 Beds
    • 2 Baths
    • 1,070 Sq Ft

    4869 Bar Neck Rd, Tilghman, MD 21671

    Discover a unique investment opportunity in the charming Victorian-style home located in the serene Tilghman Island. This detached residence, built in 1900, boasts 2 over/under units of well-maintained living space, each featuring a spacious bedroom and full bathroom. The interior is adorned with hardwood and partially carpeted floors, enhancing its classic appeal. Investors will appreciate the

    Brenda Sarver Maryland Realty Connection

    4869 Bar Neck 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
    /71

    $945,000

    $50K 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

    $489,888

    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
    /55

    $339,000

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,761 Sq Ft

    21524 Chicken Point Rd, Tilghman, MD 21671

    Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your

    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
    /119

    $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. The possibilities are endless....... Vacation Rental, 24 brand new slips, typically rent from 175.00-225.00 monthly. Develop a new fishing center, crabbing tours, sunsets cruises. Let's see what you can

    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

    $899,000

    $51K 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

Real Estate & Homes for Sale in 21671

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