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

$883,900

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 723 sqft

729 Windsor Ln, Key West, FL 33040

Old Town
Est. Refi. Payment $5,379/mo*
Refinance Your Home
Currently Off Market - Sold Mar 23, 2026 for $865,000 (9% below list price)

Home Value

Trulia Estimate
$884K
Since 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
MonthEstimated 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

  • 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

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.
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

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

Price and Tax history

DateEventPrice
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%

Market trends in Key West

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.14M
$143K
MoM
Sale-to-List Price
Price per sq ft
$865
$67
MoM
Available listings
255
17
MoM

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. "

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.

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