Change Real Estate Presents:

5480 Windward Drive
Tilghman MD 21671

For Sale: $1,250,000.00 Active

List Date: 2026-07-13

Tilghman
4 bedrooms
3 bathrooms
1,936 build ft2
31,065 land ft2

About This Property

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 Agent: Kimberly J Crouch. Benson & Mangold, LLC 410-829-7062 kcrouch@bensonandmangold.com

Property Features

Location Information
County:
Subdivision: TILGHMAN ISLAND
click to open map in a new window
Interior Features
Appliances:
Interior:
Laundry:
Furnished: None
Flooring:
Water: Well
Cooling: Central A/C
Heating: Heat Pump(s)
Fireplaces: 1
Windows:
Utilities:
Sewer: Public Sewer
Rooms
Room Type: Bedroom 4
Features: Flooring - Carpet
Level: Upper 1
Room Type: Foyer
Features: Flooring - HardWood
Level: Main
Room Type: Kitchen
Features: Flooring - HardWood
Level: Main
Room Type: Living Room
Features: Flooring - HardWood, Cathedral/Vaulted Ceiling
Level: Main
Room Type: Sun/Florida Room
Features: Flooring - HardWood, Fireplace - Gas
Level: Main
Room Type: Primary Bedroom
Features: Flooring - HardWood, Ceiling Fan(s)
Level: Main
Room Type: Primary Bathroom
Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower, Walk-In Closet(s)
Level: Main
Room Type: Bedroom 2
Features: Flooring - HardWood
Level: Main
Room Type: Bedroom 3
Features: Flooring - HardWood
Level: Main
Room Type: Office
Features: Flooring - HardWood
Level: Main
Room Type: Bathroom 2
Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
Level: Main
Room Type: Bathroom 3
Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
Level: Main
Exterior Features
Year Built: 1973
Legal Subdivision: 21050165
Subdivision Name: Tilghman Island
Garage Spaces: 1.0
Association Fee: $185.00 (Annually)
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Kimberly J Crouch. Benson & Mangold, LLC 410-829-7062 kcrouch@bensonandmangold.com

Property Photos [Click to enlarge]

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