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Street View
$1,250,000
Monthly Est:$6,222
4 Beds
- 3 Baths
3 full baths
1,936sqft
5480 Windward Dr, Tilghman, MD 21671
$1,250,000
$6,222/moEst:
Get Pre-Approved
Single Family Residence
Built in 1973
$15.42/mo HOA
31,065 sqft lot
$646/sq.ft
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.
- Houzeo last checked: 5 hours ago
- Listing updated: July 14, 2026 at 3:21 pm
- Listing Provided by: Kimberly J Crouch (410) 829-7062 | Benson & Mangold, LLC (410) 745-0415
- Source: Bright MLS-NJ | MLS#: MDTA2014484

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1973
HOA Fees
$15.42/mo
Finished Area
1,936 sqft
Lot Size
31,065 sqft lot
Basement Area
- sqft
MLS Name
Bright MLS
MLS Number
MDTA2014484
MLS Status
ACTIVE-BRIGHT
Days on Market
2

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Location
HOA Management
N/A
HOA Fees
$185/ Annually
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 3
Interior
Sewer
Public Sewer
Cooling
Central A/c
Heating
Heat Pump(s)
Construction
Year Built
Year Built: 1973
Home type
Single Family Residence
Foundation Details
Crawl Space
Architectural Style
Contemporary
Construction Materials
Vinyl Siding
Utilities & Energy
Water Source
Well
Pool Features
Concrete, In Ground
Other Features
Subdivision Name
Tilghman Island
Price History
| Date | Event | Price |
|---|---|---|
07/13/2026 Source: | Listed for Sale | $1,250,000 +110.08% $646/sqft |
06/13/2011 Source: | Sold | $595,000 $307/sqft |
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Based on information from Bright MLS through Oct 09, 2026, 02:30PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information
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