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$1,995,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,906 Sq. Ft.
  • 2 Car Garage
  • Updated 19 hours ago
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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.

Full Property Details for 5698 Leeward Ln

General

  • Price: $1,995,000
  • Taxes: $8,786 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2013838
  • Updated: 5/19/2026
  • Added to Site: 2 day(s) ago

Interior

  • Fireplace: Yes
  • Number of Fireplaces: 2

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 3
  • Main - Full Baths: 2
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 2
  • Bedrooms Main & Up: 3

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated

Exterior

  • Exterior Features: Extensive Hardscape
  • Porch/Patio/Deck: Screened, Porch(es)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Circular Driveway
  • Parking Type: Attached Garage
  • Garage Description: Garage - Front Entry

Location

  • County: TALBOT
  • Subdivision: PAW PAW COVE
  • Driving Directions: Rt 33 to Tilghman, follow road to right on Leeward Lane, property on cul de sac, 2nd to last.

School Information

  • School District: Talbot County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Private

Structural Information

  • Architectural Style: Contemporary
  • Structure Type: Detached
  • Construction: HardiPlank Type
  • Foundation: Block, Crawl Space
  • Roof: Architectural Shingle
  • Stories Description: Main, Upper 1
  • Square Feet: 3,906
  • Sq. Ft. Source: Assessor
  • Living Area: 3,906 Sq. Ft.
  • Finished Above Grnd: 3,906 Sq. Ft.
  • Year Built: 1996
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 1.48
  • Lot Size (Sq. Ft.): 64,469
  • Lot Size Source: Assessor
  • Zoning: V1

Water Features

  • Water Front: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Front Type: Bay
  • Water Front Name: Eastern Bay
  • Dock/Slip Conveys: Yes
  • Docks: 1
  • Power Boats: 2

Financial Considerations

  • Price Per Sq. Ft.: $510.75
  • Assessment Year: 2026
  • County Tax: $8,786
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,014,833
  • Tax Amount: $8,786
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 3906

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 1B

Listed by Benson & Mangold, LLC, Brian K Gearhart

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Listing agent

— 5698 Leeward Ln —

  • Brian K Gearhart

    Benson & Mangold, LLC

Listing Office Email: info@bensonandmangold.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5698 Leeward Ln

School District:Talbot County Public Schools
NameGradesDistance
Tilghman Elementary School
21374 Foster Ave, Tilghman Island, MD 21671
K-60.4 mi
St. Michaels Middle/High School
200 Seymour Avenue, Saint Michaels, MD 21663
7-128.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5698 Leeward Ln Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/19/2026
Listed
$1,995,000
146.3%
MLS
8/23/2017
Sold
$810,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5698 Leeward Ln

Year
Property Taxes
Change
Tax Assessment
Change
2023
$7,469
—
$960,000
5%
2023
$7,469
—
$916,600
5%
2023
$7,469
13%
$873,200
5%
2022
$6,589
6%
$829,800
—
2020
$6,217
1%
$829,800
—
2021
$6,164
-4%
$829,800
-4%
2020
$6,398
9%
$861,300
5%
2019
$5,881
11%
$819,033
5%
2018
$5,304
10%
$776,767
6%
2017
$4,841
3%
$734,500
2%
2016
$4,688
3%
$723,500
2%
2015
$4,553
4%
$712,500
2%
2014
$4,377
—
$701,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Benson & Mangold, LLC, Brian K Gearhart

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5698 Leeward Lane, Tilghman, MD 21671 (MLS# MDTA2013838) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 5698 Leeward Lane is currently listed for $1,995,000 and was received on May 19, 2026. Want to learn more about 5698 Leeward Lane? Do you have questions about finding other Single Family real estate for sale in Tilghman? You can browse all Tilghman real estate or contact a Coldwell Banker agent to request more information.

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