729 Windsor Lane, Key West, FL 33040
$950,000
Property Type:
Residential
Bedrooms:
2
Baths:
1
Square Footage:
723
Lot Size (sq. ft.):
2,992
Status:
Pending
Current Price:
$950,000
List Date:
5/24/2025
Last Modified:
3/03/2026
Overview
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.
Listing Details MLS# 615169
Location, Tax & Legal
- 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
- 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
Contract Information
- Listing Board
- Key West Association
- As is Rght to Inspct
- Yes
General Property Description
- Realtor.COM Type
- Residential - Single Family
- Style
- Single Family
- Waterfront
- No
- Pool
- No
- Year Built
- 1928
- Lot SqFt
- 2992
- Lot Sqft Source
- Property Data Card
- Acres
- 0.07
- Living Apx SqFt
- 723
- SqFt Source
- Property Data Card
- Total Bedrooms
- 2
- Full Baths
- Yes
- Total Baths
- Yes
- Rentals Allowed
- With Restrictions
- Min Rental Days
- 28
- Control Depth
- 0
- Total Units
- 0
Status Change Info
- Contingent
- Contingent/Show
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
- Association Fee $
- 0
Building Style
- Above Flood
- Yes
- Stories
- 1 Story
- Shotgun
- Yes
More Information
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.
Fee Includes
- None
- Yes
Dockage
- None
- Yes
Tax Exemptions
- Homestead
- Yes
Appliances
- Dishwasher
- Yes
- Dryer
- Yes
- Microwave
- Yes
- Range
- Yes
- Refrigerator
- Yes
- Stainless Steel Appliance(s)
- Yes
- Washer
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Ductless
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Floor
- Tile
- Yes
- Wood
- Yes
Interior Features
- Dade County Pine
- Yes
- Quartz Countertops
- Yes
- Storage
- Yes
Windows/Doors
- Impact Rstnce Doors
- Yes
- Wood Windows
- Yes
Vehicle Storage
- Carport
- Yes
- Off Street Parking
- Yes
- Trailer Storage
- Yes
Construction
- Frame
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Furnished
- Negotiable
- Yes
Terms
- Cash
- Yes
- Conventional
- Yes
- FHA
- Yes
- VA
- Yes
Utilities
- Cable Available
- Yes
- FKAA
- Yes
- Municipal Sewer
- Yes
Porch/Balcony
- Open Porch/Balcony
- Yes
- Patio
- Yes
Title
- Negotiable
- Yes
Exterior Features
- Detached Guest Qtrs
- Yes
- Fencing
- Yes
- Privacy Wall/Fence
- Yes
- Shed
- Yes
- Storage
- Yes
Roof
- Metal Roof
- Yes
Shutters
- Panel
- Yes
Property Features
Fee Includes:
None
Tax Exemptions:
Homestead
Waterfront:
None
Waterview:
No Waterview
Dockage:
None
Building Style:
Shotgun
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; VA
Title:
Negotiable
Listing Office:
LoKation Real Estate
Last Updated: March - 03 - 2026
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.