Change Real Estate Presents:

5698 Leeward Lane
Tilghman MD 21671

For Sale: $1,995,000.00 Active

List Date: 2026-05-19

Tilghman
5 bedrooms
4 bathrooms
3,906 build ft2
1.48 land acres

About This Property

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.

Listing Agent: Brian K Gearhart. Benson & Mangold, LLC 410-310-5179 brian@chesapeakebayproperties.com

Virtual Tours / Videos

https://my.matterport.com/show/?m=tDqgULwu3tf

Property Features

Location Information
County:
Subdivision: PAW PAW COVE
click to open map in a new window
Interior Features
Appliances:
Interior:
Laundry:
Furnished: None
Flooring:
Water: Private
Cooling: Central A/C
Heating: Heat Pump(s)
Fireplaces: 2
Windows:
Utilities:
Sewer: Public Sewer
Exterior Features
Year Built: 1996
Legal Subdivision: *
Subdivision Name: Paw Paw Cove
Exterior Features: Extensive Hardscape
Parking: Circular Driveway
Garage Spaces: 2.0
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Brian K Gearhart. Benson & Mangold, LLC 410-310-5179 brian@chesapeakebayproperties.com

Property Photos [Click to enlarge]

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This content was last refreshed on 2026-06-04 09:21 AM. Some properties which appear for sale on this website may subsequently have sold or may no longer be available.

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