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$1,895,000
Monthly Est:$9,432
5 Beds
- 4 Baths
3 full baths + 1 half bath
3,906sqft
5698 Leeward Ln, Tilghman, MD 21671
$1,895,000
$9,432/moEst:
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Single Family Residence
Built in 1996
$-- HOA
1.48 acres lot
$485/sq.ft
Description
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 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 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.
- Houzeo last checked: 4 hours ago
- Listing updated: October 1, 2026 at 4:10 pm
- Listing Provided by: Brian Gearhart (410) 310-5179 | Benson & Mangold, LLC (410) 822-6665
- Source: Bright MLS-NJ | MLS#: MDTA2013838

Property Details
Status
Pending
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1996
HOA Fees
-
Finished Area
3,906 sqft
Lot Size
1.48 acres lot
Basement Area
- sqft
MLS Name
Bright MLS
MLS Number
MDTA2013838
MLS Status
PENDING-BRIGHT
Days on Market
136

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 4
Interior
Sewer
Public Sewer
Exterior Features
Extensive Hardscape
Cooling
Central A/c
Heating
Heat Pump(s)
Construction
Year Built
Year Built: 1996
Home type
Single Family Residence
Foundation Details
Block, Crawl Space
Architectural Style
Contemporary
Roof
Architectural Shingle
Construction Materials
Hardi Plank Type
Utilities & Energy
Water Source
Private
Parking Features
Circular Driveway
Pool Features
Heated
Other Features
Patio And Porch Features
Screened, Porch
Subdivision Name
Paw Paw Cove
Price History
| Date | Event | Price |
|---|---|---|
09/15/2026 Source: | Pending | $1,895,000 -2.57% $485/sqft |
08/17/2026 Source: | Price Decreased | $1,945,000 -2.51% $498/sqft |
05/19/2026 Source: | Listed for Sale | $1,995,000 +146.30% $511/sqft |
08/23/2017 Source: | Price Decreased | $810,000 -26.36% $207/sqft |
12/05/2014 Source: | Sold | $1,100,000 $282/sqft |
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Based on information from Bright MLS through Oct 09, 2026, 02:30PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information
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