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$865,000
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Property Description
Charming Historic Gem in the Heart of Old Town Key West! Welcome to 729 Windsor Lane-a rare opportunity to own a piece of Key West history nestled in one of the island's most desirable residential neighborhoods. Set on an expansive nearly 3,000 sq.ft. lot, this classic home offers a generous footprint that's almost unheard of in Old Town, along with the luxury of coveted off-street parking. Step inside to discover a thoughtfully updated interior that blends historic charm with modern comfort. The remodeled bathroom features stylish tilework, updated fixtures, and a spa-like feel, while the upgraded kitchen boasts contemporary cabinetry, sleek countertops, and stainless steel appliances-perfect for preparing everything from a quiet Key West breakfast to tropical cocktails on the patio. Surrounded by lush native foliage, the property offers a serene, private setting just steps from Duval Street, world-class dining, art galleries, entertainment, and more-while maintaining the tranquility of a quiet residential neighborhood. For investors, the unbeatable location just a short stroll from Duval Street, renowned restaurants, nightlife, galleries, and cultural attractions makes this property ideal for monthly vacation rentals or long-term leasing to locals. For second-home buyers, it offers an effortless blend of privacy and proximity to the action, in a quiet residential neighborhood. Truly your home away from home. And for the historic home lover, this residence offers a chance to preserve and personalize a piece of Key West's architectural heritage with room to enhance over time and make it your own. With its historic architecture, upgraded amenities, and rare lot size, this home offers endless potential to create your tropical dream oasis. Whether you're looking for a charming island retreat, a vacation rental, or a full-time residence, 729 Windsor Lane delivers the perfect blend of location, lifestyle, and opportunity.
Full Property Details
Full Property Details for 729 Windsor Ln
General
- Sold For: $865,000
- Taxes: $10,361 (2024)
- Status: Closed
- Type: Single Family
- Source: 927
- MLS ID: 615169
- Added to Site: 355 day(s) ago
Interior
- Interior Features: Dade County Pine, Quartz Countertops, Storage
- Appliances: Stainless Steel Appliance(s), Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Flooring: Wood, Tile
Rooms
Bathrooms
- Total Bathrooms: 1
- Full Bathrooms: 1
Bedrooms
- Total Bedrooms: 2
Exterior
- Exterior Features: Detached Guest Qtrs, Fencing, Privacy Wall/Fence, Shed, Storage
- Deck/Patio: Open Porch/Balcony, Patio
- Porch/Patio/Deck: Open Porch/Balcony, Patio
Parking
- Parking Features: Off Street, Carport
Location
- Area: 01 - Key West
- County: Monroe
- Subdivision: William's Court (1.0)
Community
- Assoc. Fees Include: None
- Pets Allowed: Yes
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Ductless, Ceiling Fans(s)
Structural Information
- Architectural Style: Above Flood, Shotgun
- Construction: Frame
- Roof: Metal
- Windows/Doors: Impact Rstnce Doors, Wood Windows, Shutters
- Square Feet: 723
- Sq. Ft. Source: Property Data Card
- Year Built: 1928
Lot Features
- Property View: No Waterview
- Lot Size (Acres): 0.07
- Lot Size (Sq. Ft.): 2,992
- Lot Size Source: Property Data Card
- Zoning: HMDR - Historic Medium Density Residential
Water Features
- Water View: Yes
Financial Considerations
- Tax Amount: $10,361.58
- Tax Year: 2024
- Terms: Cash, Conventional, VA Loan, FHA
Disclosures and Reports
- Legal Description: KW PT OF TR 5 OR27-439/40 OR27-441/42 OR569-423/24 OR921-640/41 OR921-642 OR2694-1238 OR3159-1522 OR3269-2308
- Flood Zone: AE
- APN: 00018790-000000
Listed by LoKation Real Estate, Amber DeBevec
Sold by Keller Williams Key West Compass Realty, Elaine S Coyle
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Schools
Schools serving 729 Windsor Ln
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Horace O'bryant School 1105 Leon Street, Key West, FL 33040 | 6-8 | 0.7 mi |
Key West High School 2100 Flagler Avenue, Key West, FL 33040 | 9-12 | 1.3 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 729 Windsor Ln
Date
Details
Price
Change
Source
3/23/2026
Sold
$865,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
729 Windsor Lane, Key West, FL 33040 (MLS# 615169) is a Single Family property that was sold at $865,000 on March 23, 2026. Want to learn more about 729 Windsor Lane? Do you have questions about finding other Single Family real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.

