5480 Windward Drive, Tilghman, MD 21671

$1,195,000
  • 5480 Windward Drive, Tilghman, MD 21671 Main Photo

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ACTIVE Price Reduced by $55,000 on October 14th, 2026
BEDS4 BATHS3 full SQUARE FEET1,936 MLS#MDTA2014484
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONTILGHMAN ISLAND SCHOOLTALBOT COUNTY PUBLIC SCHOOLS

Property 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.

5480 Windward Drive | MLS# MDTA2014484

This single family home located at 5480 Windward Drive, Tilghman, MD 21671 is currently listed for sale with an asking price of $1,195,000. This property was built in 1973 and has 4 bedrooms and 3 full baths with 1936 sq. ft. Windward Drive is located in the TILGHMAN ISLAND subdivision within the TALBOT COUNTY PUBLIC SCHOOLS school district. Search TILGHMAN ISLAND real estate on www.realtymark.net today.

Property Features

Property Type: Residential - Single Family
Cooling: Central A/C
Fireplaces: 1
Fuel Type: Propane - Leased
Garage: 1
Heating: Heat Pump(s)
Home Style: Contemporary
Lot Size: 0.71 Acres
Stories: 2.0
Taxes: $5,280
Year Built: 1973

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Days on Site: 99
Exterior: Vinyl Siding
HOA Fee: $185.00/Annually
Lake Name: Chesapeake Bay
Lot Dimensions: 0.71 Acre(S)
Parking Notes: 1 Total Parking Spaces
Rooms: Living Room, Primary Bedroom, Bedroom 2,Bedroom 3,Bedroom 4,Kitchen, Foyer, Sun/Florida Room, Office, Bathroom 2,Bathroom 3,Primary Bathroom
Sewer: Public Sewer
SQFT Above Finished: 1936
SQFT Total Finished: 1936
Structure Type: Detached
Swimming Pool: Concrete, In Ground
Total Garage/Parking Spaces: 1
Water: Well

Room Sizes

Bedroom 4: 14 x 21 Level - Upper 1
Foyer: 15 x 7 Level - Main
Kitchen: 17 x 12 Level - Main
Living Room: 18 x 18 Level - Main
Sun/Florida Room: 27 x 11 Level - Main
Primary Bedroom: 12 x 13 Level - Main
Bedroom 2: 14 x 11 Level - Main
Bedroom 3: 14 x 11 Level - Main
Office: 11 x 7 Level - Main
Bathroom 2: 11 x 7 Level - Main
Bathroom 3: 9 x 5 Level - Main

Local Schools

School District: TALBOT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Benson & Mangold, LLC
Agency Phone: 4107450415

Shown By

Agency Title: RealtyMark
Agency Phone: 888-260-0040

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Estimated Payment

$ 3,448.09 per month $2,659.55 Principal & Interest $440.00 Property Tax $348.54 Homeowner's Insurance

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All commissions are negotiable Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 10/21/2026. The listing information on this page last changed on 10/21/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 10/21/2026 12:00:25 AM EST) or Stellar MLS (last updated Tue 10/20/2026 11:55:00 PM EST) or GSMLS (last updated Tue 10/20/2026 11:54:13 PM EST) or Emerald Coast MLS (last updated Tue 10/20/2026 11:55:29 PM EST) or Fort Myers (last updated Tue 10/20/2026 11:02:05 PM EST) or Central Panhandle Association of Realtors (last updated Tue 10/20/2026 11:57:29 PM EST) or Northeast Florida MLS (last updated Tue 10/20/2026 11:58:54 PM EST) or Beaches MLS (last updated Tue 10/20/2026 11:58:26 PM EST) or Naples MLS (last updated Tue 10/20/2026 11:40:21 PM EST) or Bright MLS (last updated Tue 10/20/2026 11:49:51 PM EST) or OneKey MLS (last updated Tue 10/20/2026 11:53:23 PM EST). Real estate listings held by brokerage firms other than RealtyMark may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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