$1,250,000

5480 Windward Dr, Tilghman, MD, 21671

4

Beds

3

Baths

1,936

Square feet

0.71

Acres

Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.

Listing Details

OfficeBenson & Mangold, LLC

Facts & Features

MLS® # MDTA2014484
Price $1,250,000
Bedrooms 4
Bathrooms 3.00
Full Baths 3
Square Footage 1,936
Acres 0.71
Year Built 1973
Type Residential
Sub-Type Detached
Style Contemporary
Status Active

Community Information

Address 5480 Windward Dr
Subdivision TILGHMAN ISLAND
City Tilghman
County TALBOT-MD
State MD
Zip Code 21671
Senior Community No

Amenities

# of Garages 1
Garages Additional Storage Area, Garage - Front Entry, Inside Access, Oversized
Is Waterfront Yes
Waterfront Bay
Has Pool Yes
Pool Concrete, In Ground

Interior

Heating Heat Pump(s)
Cooling Central A/C
Fireplace Yes
# of Fireplaces 1
Stories 2

Exterior

Exterior Vinyl Siding
Exterior Features Concrete,In Ground
Construction Vinyl Siding
Foundation Crawl Space
Other Structures 10000001172,10000001174

School Information

District TALBOT COUNTY PUBLIC SCHOOLS

Additional Information

Date Listed July 13th, 2026
Days on Market 53
Zoning R
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Map

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