# 5480 WINDWARD Drive, Tilghman, MD 21671 > **TL;DR:** 4bd/3ba single family, $1,250,000 ($646/sqft), built 1973, 1,936 sqft. > Pool, Fireplace, Waterfront, A/C. Est. $6,871/mo. Listed 67 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,250,000 | | Price/sqft | $646 | | Bedrooms | 4 | | Bathrooms | 3 full | | Square Feet | 1,936 | | Year Built | 1973 | | Lot Size | 30,928 sqft (0.71 acres) | | Stories | 2 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 67 | ## Why This Home Stands Out - **Pool** - Pool listed; type not specified - **Waterfront** - Waterfront location listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $6,321 | | Estimated Insurance | $365 | | HOA | $185 | | **Total** | **$6,871** | ## Key Amenities - Pool - Fireplace - Waterfront - A/C ## Property Highlights - Built in 1973 - 0.71 acre lot - 2 stories - 1 parking spaces - Private pool - Fireplace ## Description ### Agent Description 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. ## Location - **Address:** 5480 WINDWARD Drive, Tilghman, MD 21671 - **County:** TALBOT - **Neighborhood:** TILGHMAN ISLAND - **Coordinates:** 38.70153, -76.34296 - **Google Maps:** https://www.google.com/maps?q=38.70153,-76.34296 ## Listing Agent - **Name:** Kimberly J Crouch · **License:** 586315 - **Brokerage:** Benson & Mangold, LLC - **Phone:** 4108297062 - **Broker Phone:** (410) 822-1415 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/5480-Windward-Dr_Tilghman_MD_21671_M59176-99336?f=listhub&s=TRENDPA&m=MDTA2014484&c=propsimple) ## Photos ![5480 WINDWARD Drive - Photo 1](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1260181142r.jpg) ![5480 WINDWARD Drive - Photo 2](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1402796144r.jpg) ![5480 WINDWARD Drive - Photo 3](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3700765039r.jpg) ![5480 WINDWARD Drive - Photo 4](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3884537185r.jpg) ![5480 WINDWARD Drive - Photo 5](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1723084870r.jpg) ![5480 WINDWARD Drive - Photo 6](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1032732893r.jpg) ![5480 WINDWARD Drive - Photo 7](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2153113435r.jpg) ![5480 WINDWARD Drive - Photo 8](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3935545541r.jpg) ![5480 WINDWARD Drive - Photo 9](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2718987055r.jpg) ![5480 WINDWARD Drive - Photo 10](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f35124738r.jpg) ![5480 WINDWARD Drive - Photo 11](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3258156899r.jpg) ![5480 WINDWARD Drive - Photo 12](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3160848365r.jpg) ![5480 WINDWARD Drive - Photo 13](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f380611111r.jpg) ![5480 WINDWARD Drive - Photo 14](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3658755098r.jpg) ![5480 WINDWARD Drive - Photo 15](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3192137138r.jpg) ![5480 WINDWARD Drive - Photo 16](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3923345203r.jpg) ![5480 WINDWARD Drive - Photo 17](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3163168966r.jpg) ![5480 WINDWARD Drive - Photo 18](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1055737984r.jpg) ![5480 WINDWARD Drive - Photo 19](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f829249818r.jpg) ![5480 WINDWARD Drive - Photo 20](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1884155009r.jpg) ![5480 WINDWARD Drive - Photo 21](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f384229318r.jpg) ![5480 WINDWARD Drive - Photo 22](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f348606815r.jpg) ![5480 WINDWARD Drive - Photo 23](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1536123953r.jpg) ![5480 WINDWARD Drive - Photo 24](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2291214310r.jpg) ![5480 WINDWARD Drive - Photo 25](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3392032986r.jpg) ![5480 WINDWARD Drive - Photo 26](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1772184605r.jpg) ![5480 WINDWARD Drive - Photo 27](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f212283349r.jpg) ![5480 WINDWARD Drive - Photo 28](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1011915575r.jpg) ![5480 WINDWARD Drive - Photo 29](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3565805608r.jpg) ![5480 WINDWARD Drive - Photo 30](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f4218943666r.jpg) ![5480 WINDWARD Drive - Photo 31](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2944835343r.jpg) ![5480 WINDWARD Drive - Photo 32](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f741197672r.jpg) ![5480 WINDWARD Drive - Photo 33](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3311095442r.jpg) ![5480 WINDWARD Drive - Photo 34](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1995609494r.jpg) ![5480 WINDWARD Drive - Photo 35](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3462237896r.jpg) ![5480 WINDWARD Drive - Photo 36](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2275907971r.jpg) ![5480 WINDWARD Drive - Photo 37](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1398899510r.jpg) ![5480 WINDWARD Drive - Photo 38](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2305836547r.jpg) ![5480 WINDWARD Drive - Photo 39](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3285942295r.jpg) ![5480 WINDWARD Drive - Photo 40](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f4154931503r.jpg) ![5480 WINDWARD Drive - Photo 41](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2474729899r.jpg) ![5480 WINDWARD Drive - Photo 42](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3669123927r.jpg) ![5480 WINDWARD Drive - Photo 43](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f750142232r.jpg) ![5480 WINDWARD Drive - Photo 44](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2283999290r.jpg) ![5480 WINDWARD Drive - Photo 45](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1057434346r.jpg) ![5480 WINDWARD Drive - Photo 46](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2055671994r.jpg) ![5480 WINDWARD Drive - Photo 47](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3197209949r.jpg) ![5480 WINDWARD Drive - Photo 48](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1532826564r.jpg) ![5480 WINDWARD Drive - Photo 49](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1388706222r.jpg) ![5480 WINDWARD Drive - Photo 50](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2205354131r.jpg) ![5480 WINDWARD Drive - Photo 51](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f807745235r.jpg) ![5480 WINDWARD Drive - Photo 52](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2596835978r.jpg) ![5480 WINDWARD Drive - Photo 53](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2438354007r.jpg) ![5480 WINDWARD Drive - Photo 54](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f86961844r.jpg) ![5480 WINDWARD Drive - Photo 55](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f3015342740r.jpg) ![5480 WINDWARD Drive - Photo 56](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1002301045r.jpg) ![5480 WINDWARD Drive - Photo 57](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f380387605r.jpg) ![5480 WINDWARD Drive - Photo 58](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f2062509114r.jpg) ![5480 WINDWARD Drive - Photo 59](http://lh.rdcpix.com/7e4ad2cbf0600a3d3de9a8ef29327cedl-f1198848335r.jpg) --- **MLS#:** MDTA2014484 | **Updated:** 2026-09-02 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/5480-windward-drive-tilghman-md-21671-a2014484) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/5480-windward-drive-tilghman-md-21671-a2014484#listing", "url": "https://www.propertysimple.ai/listing/5480-windward-drive-tilghman-md-21671-a2014484", "name": "5480 WINDWARD Drive, Tilghman, MD 21671", "description": "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. 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