5698 LEEWARD LN, Tilghman, MD 21671

• 5 beds |
• 4 baths |
• 3,906 sqft

Property Description

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 Status:

Active

Data Last Updated:

May 21, 2026 at 6:18AM

Listing Office:

Benson & Mangold, LLC : 4108226665

Listing Agent:

Brian K Gearhart : 4103105179

MLS ID:

MDTA2013838

Interior

• A/C: Central A/C
• Heating: Heat Pump(s)Electric
• Fireplace: FireplaceFireplaces: 2
• Disability Feature: None

Exterior

• General: Extensive HardscapeAbove GradeBelow Grade
• Style: Contemporary
• Other Structures: PorchScreened
• Pool: Heated
• Parking: Circular Driveway

Construction

• Roofing: Architectural Shingle
• General: HardiPlank Type2BlockCrawl Space

Location

• Originating MLS: BRIGHT_MAIN
• School District: TALBOT COUNTY PUBLIC SCHOOLS
• County: TALBOT-MD

Lot

• Zoning: V12105189691
• Waterfront: 100

Utilities

• Water: Private
• Sewer: Public Sewer

Financial

• Source: BRIGHT_MAIN