5698 Leeward Ln, Tilghman, MD 21671
What's special
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.
- 169 days
- 106
- 9
Travel times
Living Room
Kitchen
Primary Bedroom
Zillow last checked:
Listing updated:
Brian Gearhart 410-310-5179,
Benson & Mangold, LLC 4108226665,
Listing Team: Chesapeake Bay Properties Team Of Benson & Mangold
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 3
- Main level bedrooms: 3
Basement
- Area: 0
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Electric Water Heater
Features
- Has basement: No
- Number of fireplaces: 2
Interior area
- Total structure area: 3,906
- Total interior livable area: 3,906 sqft
- Finished area above ground: 3,906
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Circular Driveway, Attached
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Screened, Porch
- Exterior features: Extensive Hardscape
- Has private pool: Yes
- Pool features: Heated, Private
- On waterfront: Yes
- Waterfront features: Bay
- Body of water: Eastern Bay
- Frontage length: Water Frontage Ft: 100
Lot
- Size: 1.48 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2105189691
- Zoning: V1
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- HardiPlank Type
- Foundation: Block, Crawl Space
- Roof: Architectural Shingle
Condition
- New construction: No
- Year built: 1996
Utilities & green energy
- Sewer: Public Sewer
- Water: Private
Community & HOA
Community
- Subdivision: Paw Paw Cove
HOA
- Has HOA: No
Location
- Region: Tilghman
Financial & listing details
- Price per square foot: $485/sqft
- Tax assessed value: $1,014,833
- Annual tax amount: $8,786
- Date on market: 5/19/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 10/1/2026 | Pending sale | $1,895,000$485/sqft |
Source: | ||
| 9/15/2026 | Price change | $1,895,000-2.6%$485/sqft |
Source: | ||
| 8/17/2026 | Price change | $1,945,000-2.5%$498/sqft |
Source: | ||
| 5/19/2026 | Listed for sale | $1,995,000+146.3%$511/sqft |
Source: | ||
| 8/25/2017 | Sold | $810,000-1.7%$207/sqft |
Source: Public Record Report a problem | ||
| 7/17/2017 | Pending sale | $824,000$211/sqft |
Source: Benson & Mangold LLC #TA9542873 Report a problem | ||
| 5/24/2017 | Listed for sale | $824,000-2.9%$211/sqft |
Source: Benson & Mangold LLC #TA9542873 Report a problem | ||
| 10/13/2016 | Listed for sale | $849,000-14.7%$217/sqft |
Source: Benson & Mangold LLC #TA9542873 Report a problem | ||
| 4/15/2016 | Price change | $995,000-9.1%$255/sqft |
Source: Benson & Mangold LLC #TA9542873 Report a problem | ||
| 12/29/2015 | Listed for sale | $1,095,000-0.5%$280/sqft |
Source: Benson & Mangold LLC #TA9542873 Report a problem | ||
| 12/9/2014 | Sold | $1,100,000-13.7%$282/sqft |
Source: Public Record Report a problem | ||
| 11/4/2014 | Pending sale | $1,275,000$326/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #TA8482186 Report a problem | ||
| 10/16/2014 | Listed for sale | $1,275,000+116.1%$326/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #TA8482186 Report a problem | ||
| 8/19/2003 | Sold | $590,000$151/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2026 | $9,438 +7.4% | $1,014,833 +5.7% |
| 2025 | $8,786 +6.1% | $960,000 +4.7% |
| 2024 | $8,277 +10.8% | $916,600 +5% |
| 2023 | $7,469 +13.4% | $873,200 +5.2% |
| 2022 | $6,589 +6% | $829,800 |
| 2021 | $6,217 | $829,800 |
| 2020 | $6,217 -3.7% | $829,800 -3.7% |
| 2019 | $6,453 +9.7% | $861,300 +5.2% |
| 2018 | $5,881 +10.9% | $819,033 +5.4% |
| 2017 | $5,304 +14.1% | $776,767 +5.8% |
| 2016 | $4,650 | $734,500 +1.5% |
| 2015 | $4,650 +19.3% | $723,500 +1.5% |
| 2014 | $3,897 | $712,500 +1.6% |
| 2013 | -- | $701,500 |
| 2012 | -- | $701,500 |
| 2011 | -- | $701,500 -21.3% |
| 2010 | -- | $890,880 +10.7% |
| 2009 | -- | $805,030 +11.9% |
| 2008 | -- | $719,180 +13.6% |
| 2007 | -- | $633,330 +8% |
| 2006 | -- | $586,392 +8.7% |
| 2005 | -- | $539,456 +68.4% |
| 2004 | -- | $320,380 +8.6% |
| 2003 | -- | $295,056 +9.4% |
| 2002 | -- | $269,733 +10.4% |
| 2001 | -- | $244,410 |
Monthly payment
Estimated market value
$1,745,200
$1.66M - $1.83M
$4,254/mo
Climate risks
Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.