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$1,250,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,936 Sq. Ft.
  • 2 Car Garage
  • Updated 10 hours ago
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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.

Full Property Details for 5480 Windward Dr

General

  • Price: $1,250,000
  • HOA FEE: $15/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,280 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2014484
  • Updated: 7/13/2026
  • Added to Site: 1 day(s) ago

Interior

  • Rooms/Areas: Living Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Foyer, Sun/Florida Room, Office, Bathroom 2, Bathroom 3, Primary Bathroom
  • Fireplace: Yes
  • Number of Fireplaces: 1

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 1
  • Bedrooms Main & Up: 3

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Concrete, In Ground

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Driveway, Attached Garage
  • Garage Description: Additional Storage Area, Garage - Front Entry, Inside Access, Oversized

Location

  • County: TALBOT
  • Subdivision: TILGHMAN ISLAND
  • Driving Directions: Rt 33 Through St. Michaels to Tilghman, right on Landing Lane, right on Windward Drive, house on left.

School Information

  • School District: Talbot County Public Schools

Community

  • Association: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Propane - Leased
  • Water Heater: Bottled Gas, Propane

Utilities

  • Sewer: Public Sewer
  • Water: Well

Structural Information

  • Architectural Style: Contemporary
  • Structure Type: Detached
  • Construction: Vinyl Siding
  • Foundation: Crawl Space
  • Stories Description: Main, Upper 1
  • Square Feet: 1,936
  • Sq. Ft. Source: Assessor
  • Living Area: 1,936 Sq. Ft.
  • Finished Above Grnd: 1,936 Sq. Ft.
  • Year Built: 1973
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 0.71
  • Lot Size (Sq. Ft.): 31,065
  • Lot Size Source: Assessor
  • Zoning: R

Financial Considerations

  • Price Per Sq. Ft.: $645.66
  • Association Fee: $185
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2026
  • County Tax: $5,280
  • County Tax Freq: Annually
  • Tax w/Assessment: $606,600
  • Tax Amount: $5,280
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1936

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: 1
  • Lot Number: 2

Listed by Benson & Mangold, LLC, Kimberly J Crouch

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Listing agent

— 5480 Windward Dr —

  • Kimberly J Crouch

    Benson & Mangold, LLC

Listing Office Email: info@bensonandmangold.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5480 Windward Dr

School District:Talbot County Public Schools
NameGradesDistance
Tilghman Elementary School
21374 Foster Ave, Tilghman Island, MD 21671
K-60.8 mi
St. Michaels Middle/High School
200 Seymour Avenue, Saint Michaels, MD 21663
7-128.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5480 Windward Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/13/2026
Listed
$1,250,000
110.08%
MLS
6/10/2011
Sold
$595,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5480 Windward Dr

Year
Property Taxes
Change
Tax Assessment
Change
2023
$4,657
—
$576,900
3%
2023
$4,657
—
$560,633
3%
2023
$4,657
11%
$544,367
3%
2022
$4,193
7%
$528,100
—
2020
$3,919
1%
$525,600
—
2021
$3,886
—
$523,100
—
2020
$3,867
7%
$520,600
3%
2019
$3,628
8%
$505,167
3%
2018
$3,344
7%
$489,733
3%
2017
$3,126
4%
$474,300
2%
2016
$3,011
4%
$464,667
2%
2015
$2,908
5%
$455,033
2%
2014
$2,779
—
$445,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Benson & Mangold, LLC, Kimberly J Crouch

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5480 Windward Drive, Tilghman, MD 21671 (MLS# MDTA2014484) is a Single Family property with 4 bedrooms and 2 full bathrooms. 5480 Windward Drive is currently listed for $1,250,000 and was received on July 13, 2026. Want to learn more about 5480 Windward Drive? Do you have questions about finding other Single Family real estate for sale in Tilghman? You can browse all Tilghman real estate or contact a Coldwell Banker agent to request more information.

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