729 Windsor Ln, Key West, FL 33040
Property image
Property image
SOLD
MAR 23, 2026

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

  • Map ViewExplore the area around 729 Windsor Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

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.
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). It is currently off market. The Trulia Estimate is $874,700, with a rent estimate of $3,570/month.

Home Details for 729 Windsor Ln

Interior Features

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 Features

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

Property Information

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 & Status

Price
List Price: $950,000Price Per Sqft: $1,196/sqft

Active Status

MLS Status: Closed

Location

Direction & Address
City: Key WestCommunity: William's Court (1.0)

Building

Building Area
Building Area: 723 Square Feet

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 3049.2 sqft

Offer

Listing Terms: Cash, Conventional, FHA

Miscellaneous

Mls Number: 615169
Last check for updates: 1 day 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

DatePriceEventSource
03/23/2026$865,000Sold
FLKMLS #615169
03/03/2026$950,000PendingFLKMLS #615169
02/23/2026$950,000ContingentFLKMLS #615169
01/12/2026$950,000PriceChange
Key West AOR #615169
11/19/2025$1,175,000PriceChange
FLKMLS #615169
08/23/2025$1,195,000PriceChange
Key West AOR #615169
05/24/2025$1,395,000Listed For SaleFLKMLS #615169
03/19/2018$1,200,000ListingRemovedAgent Provided
07/11/2017$1,200,000PriceChange
Agent Provided
04/04/2017$1,285,000PriceChange
Agent Provided
02/12/2017$1,300,000Listed For SaleAgent Provided

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83K
MoM
Sale-to-List Price
94.6%
0.3%
MoM
Price per sq ft
$958
$15
MoM
Available listings
288
17
MoM
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Property Tax and Assessment

Year2025
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

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Assigned Schools

These are the assigned schools for 729 Windsor Ln.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

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.
  • David Atkinson
    "I so look forward to getting to Key West. I volunteer at the Tropic and love it. It feels like home."
  • Trulia User
    "Dogs are welcomed at 90% of the restaurants. Everyone will remember your dogs name but not yours! I love living here with my dog Jack."
  • Trulia User
    "Key West is a huge dog community. They even are allowed in some restaurants . When I walk my dog on the main tourist street (Duval St) I get stopped many times from people wanting to pet my dog. A group of dog owners meet up at the park in the morning every day."
  • Sgarvin3281
    " Bikes are all you need small island. Safe and secure. No commute I do t work here it is a vacation community."
  • Trulia User
    "Everywhere dogs are welcome here in key west, Florida. Come joining us here in key west. Most food and service places, boats, and entertainment venues are good with dogs."
  • Trulia User
    "Feels very safe, super clean, super walkable in old town, and Catholic school looks very vibrant. "
  • Trulia User
    "Great people, great neighborhood, great police, family friendly events. Lots of things to do within a decent drive. Very family friendly generally "
  • Key W. B. F.
    "Gatherings on the local Mangia Mangia bench at 900 Southard street, safe & friendly town. Feel connected & welcomed in Key West. Enjoy the peaceful neighborhood & the tropical weather! You can walk or bike to everything you need & want!"
  • Kfowler
    "I am not currently aware of any neighborhood events that would bring the neighbors closer. However, both my husband and I would be open to any such event that would do so and would improve the neighborhood. The area is beautiful and well maintained, with a few exceptions. "
  • Hannah B.
    "Vintage Cottage houses, small island feel, Duval Street in a few minutes with hundreds of worldly trendy restaurants "
  • Drlynmar
    "Neighborhood newsletter. Proximity to OldTown events, festivals and parades. Walk to everything. Parks, beaches, dog park. Grocery and restaurant delivery. "
  • Venomousink1970
    "the neighborhood is great I myself do not like living in Key West anymore and looking to relocate and Asheville North Carolina or the surrounding areas people are very friendly here except for the homeless vagrants that beg for money and yell at you when you don't give them any"
  • Lorettamdt
    "Old Town is historic. Our neighbors are friendly. We walk everywhere. No need for a car. Restaurants are within walking distance. Beaches are a bicycle ride away. "
  • mangiamangia
    "Lived in this neighborhood for 25 years. Walk and anywhere. Far enough of Duval to escape the noise and drunks."
  • Sajsk
    "vacationed in that area -- charming and great location and amenities, yet quiet."
  • Rjones
    "This is a great street and great neighborhood. Qiet, yet close enough to Duval and White streets to enjoy all Key West has to offer. "

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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.