Features & Amenities

Interior

  • Total Bedrooms

    5

  • Bathrooms

    3

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    3906.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Central Air, Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Electric, Heat Pump

  • Main Level Bedrooms

    3

  • Pet friendly

    N/A

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Vinyl Siding

  • Parking

    Circular Driveway, Garage, Attached

  • Pool

    Yes

  • Pool Features

    Private

  • Waterfront YN

    YES

Area & Lot

  • Lot Features

    Waterfront

  • Lot Size(acres)

    1.48

  • Lot Size(square feet)

    64469.0

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Contemporary

Price

  • Sales Price

    $1,995,000

  • Tax Amount

    $8,786

  • Sq. Footage

    3, 906

  • Price/SqFt

    $510

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • New Construction

    NO

  • Association Amenities

    Powered Boats Allowed, Boat Slip

  • Foundation Details

    Block

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    1B

  • Water Source

    Private

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Listing Courtesy of Brian K Gearhart , Benson & Mangold, LLC

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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 soaring vaulted ceilings, a gas fireplace, dramatic floor-to-ceiling windows that capture breathtaking panoramic water views, and stunning sunsets. Every detail of the renovation was carefully considered to enhance both comfort and connection to the outdoors, including the addition of a screened porch with vaulted ceilings and its own fireplace—an ideal space for year-round waterfront entertaining and relaxation.

The first-floor primary suite offers a private sanctuary overlooking the Bay, complete with expansive water views, a spacious en suite bath, and generous walk-in closets. Designed for effortless indoor-outdoor living, the home also features low-maintenance composite decking, multiple waterfront gathering spaces, and a heated gunite pool perfectly positioned to enjoy the surrounding scenery.

For boating enthusiasts, the property is equally exceptional. A private dock equipped with a boat lift and jet ski lift provides immediate access to some of the Eastern Shore’s finest boating, fishing, and waterfront destinations. The protected rip-rapped shoreline adds both beauty and peace of mind.

This is a rare opportunity to own a turnkey waterfront escape offering luxury, privacy, and unforgettable Chesapeake Bay sunsets—all within the laid-back charm and timeless appeal that make Tilghman Island so special.

5698 LEEWARD LANE

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Related Properties

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 framed by expansive windows that fill the home with ethereal lighting. Designed for both the passionate cook and the gracious host, the gourmet kitchen features professional-grade Wolf appliances, a Cambria quartz oversized island, and custom cabinetry. The main level primary suite offers panoramic views of Harris Creek, custom millwork, and a spa-worthy bath showcasing a deep soaking tub and beautifully tiled shower. An additional main-level bedroom with private ensuite provides ideal accommodations for guests. On the second floor, three spacious bedrooms await. One a second private primary suite with custom closet and balcony. Two bedrooms, sharing a thoughtfully designed Jack and Jill bath, all centered around a loft-style lounge. Additional amenities include a thoughtfully designed mudroom and a garage with epoxy-coated floors and sleek Clopay glass garage doors. The covered porch creates a seamless space for indoor-outdoor entertaining. Situated on a large, private lot within an exclusive HOA waterfront community, the property offers a rare sense of seclusion while still providing access to coveted amenities such as a community dock and pool. With all new electric, plumbing, HVAC and more, this house has been taken down to the studs and rebuilt to its timeless architecture. From its elevated finishes to its extraordinary setting, 21485 Island Club Drive captures the essence of luxury coastal living on Maryland’s Eastern Shore.
#MDTA2010266

TILGHMAN

21485 ISLAND CLUB ROAD

5 Beds

4 Baths

4,303 Sq.Ft.

$1,950,000

MLS#: MDTA2010266

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