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For salePrice cut: $50K (8/17)
$1,945,000
5beds
3,906sqft

5698 Leeward Ln, Tilghman, MD 21671

5beds
3,906sqft
Single family residence
Built in 1996
1.48 Acres
2 Attached garage spaces
$498 price/sqft

What's special

Gas fireplaceProtected rip-rapped shorelineLow-maintenance composite deckingMultiple waterfront gathering spacesSoaring vaulted ceilingsDramatic floor-to-ceiling windowsGenerous walk-in closets

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.

103 days
|
1,912
|
121
|
Source: Bright MLS,MLS#: MDTA2013838MLS Logo
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Brian Gearhart 410-310-5179,

Benson & Mangold, LLC 4108226665,

Listing Team: Chesapeake Bay Properties Team Of Benson & Mangold

Source: Bright MLS,MLS#: MDTA2013838MLS Logo

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: $498/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

DateEventPrice
8/17/2026Price change$1,945,000-2.5%$498/sqft
Source: Bright MLS #MDTA2013838 Report a problem
5/19/2026Listed for sale$1,995,000+146.3%$511/sqft
Source: Bright MLS #MDTA2013838 Report a problem
8/25/2017Sold$810,000-1.7%$207/sqft
Source: Public Record Report a problem
7/17/2017Pending sale$824,000$211/sqft
Source: Benson & Mangold LLC #TA9542873 Report a problem
5/24/2017Price change$824,000-2.9%$211/sqft
Source: Benson & Mangold LLC #TA9542873 Report a problem
10/13/2016Price change$849,000-14.7%$217/sqft
Source: Benson & Mangold LLC #TA9542873 Report a problem
4/15/2016Price change$995,000-9.1%$255/sqft
Source: Benson & Mangold LLC #TA9542873 Report a problem
12/29/2015Listed for sale$1,095,000-0.5%$280/sqft
Source: Benson & Mangold LLC #TA9542873 Report a problem
12/9/2014Sold$1,100,000-13.7%$282/sqft
Source: Public Record Report a problem
11/4/2014Pending sale$1,275,000$326/sqft
Source: Chesapeake Bay Real Estate Plus, LLC #TA8482186 Report a problem
10/16/2014Listed for sale$1,275,000+116.1%$326/sqft
Source: Chesapeake Bay Real Estate Plus, LLC #TA8482186 Report a problem
8/19/2003Sold$590,000$151/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
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

Find assessor info on the county website

Monthly payment

Est. payment
$10,854/mo
Principal & interest
$9784
Property taxes
$1070
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Estimated market value

Not available

Estimated sales range

Not available

Not available

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 21671

Nearby schools

Tilghman Elementary School
Grades PK-50.4 miles
2/10
GreatSchools® Rating
Test Score Rating
3/10
Student Progress Rating
1/10
St. Michaels Middle/High School
Grades 6-128.4 miles
6/10
GreatSchools® Rating
Test Score Rating
6/10
College Readiness Rating
8/10
Student Progress Rating
3/10