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5698 Leeward Ln, 
Tilghman, MD 21671

$1,995,000


5

Beds


4

Baths


3,906

Sq Ft


Single Family

Active

Listed by

Brian K Gearhart

Benson & Mangold, LLC., 4108226665, info@bensonandmangold.com

Last updated:

May 25, 2026, 01:42 PM

MLS#

MDTA2013838

Source:

BRIGHTMLS

About This Home

5698 Leeward Ln

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.

Home Facts

Single Family

4 Baths

5 Bedrooms

Built in 1996

Price Summary

1,995,000

$510 per Sq. Ft.

MLS #:

MDTA2013838

Last Updated:

May 25, 2026, 01:42 PM

Added:

6 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

3,906 Sq. Ft.


Structure

Structure

Architectural Style:

Contemporary

Building Area:

3,906 Sq. Ft.

Year Built:

1996


Lot

Lot Size (Sq. Ft):

64,468


Finances & Disclosures

Finances

Price:

$1,995,000

Price per Sq. Ft:

$510 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.