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MLS: #MDTA2014484, Listed By: Kimberly Crouch, Benson & Mangold, LLC, Source:Bright MLS

5480 Windward Drive

TILGHMAN, MD 21671
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Bed 4

Bed

Bath 3

Bath

SqFt1,936

Sqft

Acres0.71

Acre(Lot)

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 th e 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.

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Detail Ic Property Details

Property Type : Residential

Price : $1,250,000

AD Id : 88023934

MLS Id : MDTA2014484

Beds : 4

Lot Size : 0.71 Acre

Living Area Size : 1,936

Year Built : 1973

Garage : 1

County : TALBOT

Subdivision: Tilghman Island

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Feature Features

  • Bedroom Information

    Total beds: 4

    Bathroom Information

    Total Baths: 3 Full Baths: 3

    Room Information

    Basement: Crawl Space
  • Interior Features

    Appliances: Gas Water Heater
  • Heating & Cooling

    Has Heating: Yes Heating: Propane, Heat Pump Has Cooling: Yes Cooling: Central Air, Electric Water front: 1

  • Building Information

    Year Built: 1973 Building Area Total: 1936 Construction Materials: Vinyl Siding Frontage Length: 110 Pool Features: In Ground, Private Private Pool: Yes Association Fee Frequency: Annually

  • Lot Information

    Lot Size Acres: 0.71 Lot Size Source: Assessor Lot Size Square Feet: 31065 Lot Description: Waterfront

    Property Information

    Subdivision: TILGHMAN ISLAND Source Property Type: Residential Property SubType: Single Family Residence Levels: Two Property Age: 53

  • Listing Price Information

    Listing Price: $1250000

  • Tax Information

    Parcel Number: 2105187656 Tax Lot: 2 Tax Year: 2025 Annual Tax: $5280

  • Parking Information

    Parking Total: 1 Oversized, Garage, Driveway, Inside Entrance, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 1
    Homeowners Association Information
    Has Association: Yes HOA: $185.00

  • Location Information

    Direction: Rt 33 Through St. Michaels to Tilghman, right on Landing Lane, right on Windward Drive, house on left. WaterSource: Well
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
21642 Chicken Point Road, Tilghman, MD, 21671 $2,475,000 7 6 4,151 4,151 SqFt
21647 Camper Circle, Tilghman, MD, 21671 $325,000 3 1 1,262 1,262 SqFt
21485 Island Club Road, Tilghman, MD, 21671 $1,950,000 5 5 4,303 4,303 SqFt
21572 Chicken Point Road, Tilghman, MD, 21671 $899,000 2 3 1,729 1,729 SqFt
21560 Chicken Point Road, Tilghman, MD, 21671 $845,000 3 2 1,314 1,314 SqFt
21552 Chicken Point Road, Tilghman, MD, 21671 $945,000 5 2 2,655 2,655 SqFt
21477 Island Club Road, Tilghman, MD, 21671 $1,150,000 4 3 3,040 3,040 SqFt
21524 Chicken Point Road, Tilghman, MD, 21671 $339,000 4 2 1,761 1,761 SqFt
21527 Chicken Point Road, Tilghman, MD, 21671 $350,000 3 1 1,144 1,144 SqFt
4938 Fairbank Road, Tilghman, MD, 21671 $975,000 4 3 2,850 2,850 SqFt

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 07/19/2026 @ 18:16

MLS: MDTA2014484 LISTED BY: Kimberly Crouch, Benson & Mangold, LLC 410-745-0415 SOURCE: Bright MLS

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