729 Windsor Ln
Key West, FL 33040
Old Town- 2 Beds
- 1 Bath
- 723 sqft
$865,000
Last Sold: Mar 23, 2026
9% below list $950K
$1,196/sqft
Est. Refi. Payment $5,086/mo*
$865,000
Last Sold: Mar 23, 2026
9% below list $950K
$1,196/sqft
Est. Refi. Payment $5,086/mo*
2 Beds
1 Bath
723 sqft
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1928
Living Area
723 sqft
Price/Sqft
$1,196/sqft
HOA
None
About this House
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.
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.
Home Details for 729 Windsor Ln
|
|---|
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 1Number of Bathrooms (full): 1 |
Dimensions and Layout Living Area: 723 Square Feet |
Appliances & Utilities Utilities: Cable AvailableAppliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Microwave, Stainless Steel Appliance(s)DishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Has CoolingAir Conditioning: Ceiling Fans(s),Ductless |
Windows, Doors, Floors & Walls Flooring: Tile, Wood |
Levels, Entrance, & Accessibility Floors: Tile, Wood |
View No View |
|
|---|
Exterior Home Features Patio / Porch: Open Porch/Balcony, PatioFencing: Fenced, PrivacyOther Structures: Guest House, Shed(s)Exterior: StorageNo Private Pool |
Parking & Garage No Attached GarageParking: Storage |
Frontage Not on Waterfront |
|
|---|
Year Built Year Built: 1928 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Shotgun |
Building Construction Materials: Frame |
Property Information Parcel Number: 00018790000000 |
|
|---|
Price List Price: $950,000Price Per Sqft: $1,196/sqft |
|
|---|
MLS Status: Closed |
|
|---|
|
|---|
Direction & Address City: Key WestCommunity: William's Court (1.0) |
|
|---|
Building Area Building Area: 723 Square Feet |
|
|---|
HOA Fee Includes: NoneNo HOA |
|
|---|
Lot Area: 3049.2 sqft |
|
|---|
Listing Terms: Cash, Conventional, FHA |
|
|---|
Mls Number: 615169 |
Last check for updates: about 3 hours ago
Listed by Amber DeBevec
LoKation Real Estate
Bought with: Elaine S Coyle, (305) 923-9202, Keller Williams Key West Compass Realty
Source: FLKMLS, MLS#615169

Price History for 729 Windsor Ln
| Date | Price | Event | Source |
|---|---|---|---|
| 03/23/2026 | $865,000 | Sold | FLKMLS #615169 |
| 03/03/2026 | $950,000 | Pending | FLKMLS #615169 |
| 02/23/2026 | $950,000 | Contingent | FLKMLS #615169 |
| 01/12/2026 | $950,000 | PriceChange | Key West AOR #615169 |
| 11/19/2025 | $1,175,000 | PriceChange | FLKMLS #615169 |
| 08/23/2025 | $1,195,000 | PriceChange | Key West AOR #615169 |
| 05/24/2025 | $1,395,000 | Listed For Sale | FLKMLS #615169 |
| 03/19/2018 | $1,200,000 | ListingRemoved | Agent Provided |
| 07/11/2017 | $1,200,000 | PriceChange | Agent Provided |
| 04/04/2017 | $1,285,000 | PriceChange | Agent Provided |
| 02/12/2017 | $1,300,000 | Listed For Sale | Agent Provided |
Market trends in Key West
Last updated June 2026
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $10,681 |
| Assessment | $1,276,457 |
Home facts updated by county records
Comparable Sales for 729 Windsor Ln
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.14 | Single-Family Home | $865,000 | 05/15/26 | 1 | 1 | 510 | |
0.23 | Single-Family Home | $861,700 | 08/19/25 | 2 | 1 | 610 | |
0.13 | Single-Family Home | $1,000,000 | 07/07/26 | 1 | 1 | 594 | |
0.08 | Single-Family Home | $875,000 | 09/30/25 | 3 | 2 | 1,049 | |
0.09 | Single-Family Home | $1,595,000 | 09/12/25 | 2 | 2 | 860 | |
0.07 | Single-Family Home | $1,400,000 | 04/02/26 | 1 | 1 | 684 | |
0.11 | Single-Family Home | $1,525,000 | 09/30/25 | 2 | 2 | 1,025 | |
0.18 | Single-Family Home | $780,000 | 01/07/26 | 2 | 2 | 648 | |
0.38 | Single-Family Home | $1,075,000 | 10/07/25 | 2 | 1 | 840 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 729 Windsor Ln.
What Locals Say about Old Town
At least 1 Trulia users voted on each feature.
100 % Say it's dog friendly
100 % Say people would walk alone at night
100 % Say there are sidewalks
100 % Say streets are well-lit
100 % Say neighbors are friendly
100 % Say it's quiet
100 % Say it's walkable to grocery stores
100 % Say it's walkable to restaurants
100 % Say parking is easy
100 % Say car is needed
67 % Say there's holiday spirit
60 % Say they plan to stay for at least 5 years
50 % Say there are community events
50 % Say kids play outside
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
Homes for sale near 729 Windsor Ln
Off Market Homes Near 729 Windsor Ln

MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.

