729 Windsor Lane, Key West, FL 33040
$1,175,000
Property Type:
Residential
Bedrooms:
2
Baths:
1
Square Footage:
723
Lot Size (sq. ft.):
2,992
Status:
Active
Current Price:
$1,175,000
List Date:
5/24/2025
Last Modified:
12/07/2025
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.
More Information MLS# 615169
Contract Information
Listing Board: Key West Association
As is Rght to Inspct: Yes
Current Price: $1,175,000
Listing Date: 2025-05-24
List Price: $1,175,000
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: AE
Alternate Key #: 1019445
Parcel #: 00018790-000000
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: Unknown
Legal: 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
Taxes: 10361.58
Tax Year: 2024
Pub Sewer HkUp: Yes
Street #: 729
Street Name: Windsor
Street Suffix: Lane
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: William's Court (1.0)
Area: 01 - Key West
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: No
Control Depth: 0
Lot SqFt: 2992
Pool: No
Lot Sqft Source: Property Data Card
Total Units: 0
Acres: 0.07
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 1928
Living Apx SqFt: 723
Total Bedrooms: 2
Full Baths: 1
Total Baths: 1
Remarks & Misc
Remarks – Consumer: 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.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
None: 1
Tax Exemptions
Homestead: 1
Appliances
Dishwasher: 1
Dryer: 1
Microwave: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Ductless: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Tile: 1
Wood: 1
Interior Features
Dade County Pine: 1
Quartz Countertops: 1
Storage: 1
Building Style
Above Flood: Yes
Conch: 1
Stories: 1 Story
Windows/Doors
Impact Rstnce Doors: 1
Wood Windows: 1
Vehicle Storage
Carport: 1
Off Street Parking: 1
Trailer Storage: 1
Construction
Frame: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Negotiable: 1
Terms
Cash: 1
Conventional: 1
FHA: 1
Seller Finance Psble: 1
VA: 1
Utilities
Cable Available: 1
FKAA: 1
Municipal Sewer: 1
Porch/Balcony
Open Porch/Balcony: 1
Patio: 1
Title
Negotiable: 1
Exterior Features
Detached Guest Qtrs: 1
Fencing: 1
Privacy Wall/Fence: 1
Shed: 1
Storage: 1
Roof
Metal Roof: 1
Shutters
Panel: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: Homestead
Waterfront: None
Waterview: No Waterview
Dockage: None
Building Style: Conch
Vehicle Storage: Carport; Off Street Parking; Trailer Storage
Furnished: Negotiable
Cooling: Ceiling Fans(s); Ductless
Utilities: Cable Available; FKAA; Municipal Sewer
Interior Features: Dade County Pine; Quartz Countertops; Storage
Appliances: Dishwasher; Dryer; Microwave; Range; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Detached Guest Qtrs; Fencing; Privacy Wall/Fence; Shed; Storage
Construction: Frame
Shutters: Panel
Floor: Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional; FHA; Seller Finance Psble; VA
Title: Negotiable
Listing Office:
LoKation Real Estate
Last Updated: December - 07 - 2025
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
