$883,900
- 2 Beds
- 1 Bath
- 723 sqft
729 Windsor Ln, Key West, FL 33040
Est. Refi. Payment $5,379/mo*
Refinance Your HomeCurrently Off Market - Sold Mar 23, 2026 for $865,000 (9% below list price)
Home Value
Trulia Estimate
$884KSince last month
Increased$8K (+0.9%)Since last year
Decreased$193K (-17.9%)Since last sale
Increased$19K (+2.2%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +78% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $884K |
| August 2026 | $876K |
| July 2026 | $872K |
| June 2026 | $867K |
| May 2026 | $860K |
| April 2026 | $863K |
| March 2026 | $865K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.14 | Single-Family Home | $865,000 | 05/15/26 | 1 | 1 | 510 | |
0.13 | 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 | |
0.07 | 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 | |
0.48 | Single-Family Home | $736,000 | 08/10/26 | 2 | 1 | 760 | |
0.38 | Single-Family Home | $1,075,000 | 10/07/25 | 2 | 1 | 840 | |
0.16 | Single-Family Home | $1,400,000 | 03/31/26 | 2 | 2 | 1,200 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.04 | $2,619,500 | 3 | 2.5 | 1,524 | Off Market | |
0.02 | $1,405,700 | 3 | 2 | 1,268 | Off Market | |
0.02 | $1,665,100 | 3 | 2.5 | 1,524 | Off Market | |
0.07 | $1,749,100 | 3 | 2.5 | 1,714 | Off Market | |
0.05 | $3,299,700 | 4 | 3.5 | 3,353 | Off Market | |
0.07 | $1,400,000 | 1 | 1 | 684 | Recently Sold | |
0.08 | $2,599,000 | 3 | 2 | 1,204 | For Sale | |
0.02 | $1,359,200 | 2 | 2 | 1,060 | Off Market | |
0.03 | $618,000 | 1 | 1 | 599 | Off Market | |
0.05 | $1,315,500 | 2 | 2 | 1,224 | Off Market | |
0.08 | $1,625,000 | 3 | 2 | 1,594 | Recently Sold |
Local Information
-- mins to
Home Highlights
Single-Family Home
Built in 1928
723 sqft
$1,196/sqft
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.
729 Windsor Ln, Key West, FL 33040 is a 2 bedroom, 1 bathroom, 723 sqft single-family home in Old Town, built in 1928. It last sold for $865,000 on Mar 23, 2026 (9% below the $950,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $883,900, with a rent estimate of $3,324/month.
Last check for updates: about 1 hour 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

Home Details for 729 Windsor Ln
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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 |
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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 |
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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 |
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Price List Price: $950,000Price Per Sqft: $1,196/sqft |
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MLS Status: Closed |
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Direction & Address City: Key WestCommunity: William's Court (1.0) |
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Building Area Building Area: 723 Square Feet |
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HOA Fee Includes: NoneNo HOA |
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Lot Area: 3049.2 sqft |
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Listing Terms: Cash, Conventional, FHA |
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Mls Number: 615169 |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Mar 23, 2026 Source: FLKMLS #615169 | Sold | $865,000 |
Mar 3, 2026 Source: FLKMLS #615169 | Pending | $950,000 |
Feb 23, 2026 Source: FLKMLS #615169 | Contingent | $950,000 |
Jan 12, 2026 Source: Key West AOR #615169 | PriceChange | $950,000 Price decreased by 19% |
Nov 19, 2025 Source: FLKMLS #615169 | PriceChange | $1,175,000 Price decreased by 2% |
Aug 23, 2025 Source: Key West AOR #615169 | PriceChange | $1,195,000 Price decreased by 14% |
May 24, 2025 Source: FLKMLS #615169 | Listed For Sale | $1,395,000 |
Mar 19, 2018 Source: Agent Provided | ListingRemoved | $1,200,000 |
Jul 11, 2017 Source: Agent Provided | PriceChange | $1,200,000 Price decreased by 7% |
Apr 4, 2017 Source: Agent Provided | PriceChange | $1,285,000 Price decreased by 1% |
Feb 12, 2017 Source: Agent Provided | Listed For Sale | $1,300,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $10,681 | $1,276,457 |
Home facts updated by county records
Market trends in Key West
Last updated August 2026
Avg. sale price
$1.14M
$143KMoM
Sale-to-List Price
—
Price per sq ft
$865
$67MoM
Available listings
255
17MoM
Around this home
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

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.
Frequently asked questions about 729 Windsor Ln
- What is 729 Windsor Ln estimated to be worth?Trulia's estimated value for 729 Windsor Ln in Key West, FL is $883,900.
- What is the price history for 729 Windsor Ln?729 Windsor Ln in Key West, FL last sold for $865,000 in March 2026.
- Is Key West a buyer's or seller's market?Key West is currently a buyer's market, based on recent for-sale activity.
- What's the median sale price in Key West?The median sale price in Key West is $1.14M. That is down $143K from the prior month.
- Does 729 Windsor Ln have air conditioning?Yes, 729 Windsor Ln in Key West, FL has air conditioning.
- Does 729 Windsor Ln have laundry facilities?Yes, 729 Windsor Ln in Key West, FL has in-unit laundry.

