5698 Leeward Lane
Tilghman, MD, 21671 $ 1,895,000
Bedrooms5 Baths3.1 Sq 3,906 Monthly Estimate*
$ 11,965
for $1,895,000 with 5 bedrooms and 3 full baths, 1 half bath. This 3,906 square foot home was built in 1996 on a lot size of 1.48.
Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat on 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. Offered fully furnished, the home provides a truly turnkey opportunity, allowing the next owner to immediately enjoy the Chesapeake Bay lifestyle. 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 Shores 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 fully furnished, 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.
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FeaturesGeneralLiving Area 3906
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Central A/C
Possession Settlement
Roof Architectural Shingle
Zoning V1
Garage Spaces 2.00
Patio/Porch Features Screened Porch(es)
Architectural Style Contemporary
Pool Features Heated
Construction Materials HardiPlank Type
School District TALBOT COUNTY PUBLIC SCHOOLS
Year Built 1996
Levels 2
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County TALBOT
New Construction N
Property Type Residential
HOA N
Subdivision Name PAW PAW COVE
Garage Y/N Y
Water Access Y/N Y
Other Structures Above Grade Below Grade
Full Baths 3
Status ACTIVE
Directions Rt 33 to Tilghman follow road to right on Leeward Lane property on cul de sac 2nd to last.
City TILGHMAN
Body of Water Eastern Bay
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 64469.00
Tax Annual Amount 8786.0
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 2
Bathrooms Count Main Level 3.00
Price Per Sq Ft Total AG 485.15
Vacation Rental Y/N N
Virtual Tour https://my.matterport.com/show/?m=tDqgULwu3tf
Standard Status Active
Year Built Source Assessor
Legal Subdivision *
Tax Lot 1B
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InteriorHeating Fuel Electric
Total Fireplaces 2
Hot Water Electric
Basement (Y/N) N
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 3906
Half Baths 1
Central Air Y/N Y
Total Bedrooms 5
Below Grade Finished Area 0
Main Level Bedrooms 3
Below Grade Finished Area Unit Type Square Feet
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 4
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ExteriorExterior Amenities Extensive Hardscape
Pool Yes - Personal
Parking Features Circular Driveway
Water Source Private
Garage Features Garage - Front Entry
Type of Parking Attached Garage
Foundation Details Block Crawl Space
Water View Y/N N
Lot Size Acres 1.48
Water Body Type Bay
Lot Size Source Assessor
Waterfront Y/N Y
Number of Docks 1
Land Assessed Value 476000.00
Navigable Water Y/N Y
Number of Slips 2
Water Oriented Y/N Y
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* Excluded FeaturesList ByBenson & Mangold, LlcBroker
brian@chesapeakebayproperties.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $11,965
- Monthly Property Taxes
- $732
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Tilghman, MD
Average List Price $920,916
Percent of Sale Price 51%
About Tilghman, MD 721 Population
-11% Since 2002
$ 68,182 Median Income
57.08 Median Age
8% Households with Children
Trends Information provided by ATTOM Data Solutions.
3533924 Elementary School
3534231 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 9/15/2026 | $1,895,000 | -2.57% | Price Down |
| 8/17/2026 | $1,945,000 | -2.51% | Price Down |
| 5/19/2026 | $1,995,000 | | Listed Price |