1009 Windsor Ln, Key West, FL 33040
Property image
Property image
OFF MARKET

$3,601,900

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 3,360 sqft

1009 Windsor Ln, Key West, FL 33040

Old Town
Est. Refi. Payment $21,823/mo*
Refinance Your Home
Currently Off Market - Sold Feb 2, 2024 for $3,250,000

Home Value

Trulia Estimate
$3.6M
Since last month
Decreased$84K (-2.3%)
Since last year
Increased$194K (+5.7%)
Since last sale
Increased$352K (+10.8%)
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 +74% in the last 10 years
MonthEstimated value
2026
August 2026$3.6M
July 2026$3.69M
June 2026$3.67M
May 2026$3.59M
April 2026$3.65M
March 2026$3.55M
February 2026$3.55M
January 2026$3.47M
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
0.09
Single-Family Home
$3,422,500
03/12/26
5
5.5
3,006
0.12
Single-Family Home
$2,750,000
06/29/26
5
4.5
2,721
0.15
Single-Family Home
$3,100,000
04/22/26
5
4
2,349
0.28
Single-Family Home
$4,225,000
03/16/26
5
5.5
3,434
0.47
Single-Family Home
$3,300,000
05/21/26
5
6
3,667
0.29
Single-Family Home
$4,250,000
05/28/26
3
3.5
2,833
0.43
Single-Family Home
$4,300,000
04/09/26
4
4.5
3,624
0.32
Single-Family Home
$3,400,000
11/07/25
3
3.5
1,890
0.38
Single-Family Home
$3,350,000
12/03/25
3
3.5
2,438
0.41
Single-Family Home
$3,750,000
10/20/25
4
3
2,173

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
0.07
$905,000
2
1.5
896
Recently Sold
0.07
$682,900
2
1.5
896
Off Market
0.07
$935,500
2
1.5
896
Off Market
0.06
$3,668,600
4
3.5
2,400
Off Market
0.07
$1,048,900
3
3
-
Off Market
0.07
$700,000
2
1
745
Recently Sold
0.07
$581,200
2
1
745
Off Market
0.07
$779,000
2
2
648
For Sale
0.07
$1,175,000
2
2
896
Recently Sold
0.09
$1,216,500
2
2
1,062
Off Market
0.09
$599,000
3
2
1,216
Recently Sold

Local Information

  • Map ViewExplore the area around 1009 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
3,360 sqft
$1,072/sqft
Open Parking

About this House

One of a kind Historic hideaway on Windsor lane in old town Key West. This 5 bedroom 5 bathroom residence features a 720 square foot eyebrow style guest cottage overlooking the lush / private landscaped back yard and the oversized in ground pool. Open the french doors and enjoy the tropical indoor - outdoor living. The 2,640 square foot main house has 4 bedrooms 3 full baths and one half bath. Multiple off street parking spaces. Fully fenced in yard. Located just a few blocks away from the world famous Duval Street in the X flood zone. This home is offered fully furnished and is currently part of a vacation rental program. Both houses have separate meters. This allows for the guest house to legally have its own kitchen and can be rented separately from the main house.
1009 Windsor Ln, Key West, FL 33040 is a 5 bedroom, 5 bathroom, 3,360 sqft single-family home in Old Town, built in 1928. It last sold for $3,250,000 on Feb 2, 2024 (3% below the $3,347,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,601,900.
Last check for updates: about 10 hours ago
Listed by Justyn Ewald, (305) 587-7330
Expert Realty LLC (HQ)
Bought with: Terry L Garcia, (305) 923-5124, Keller Williams Key West Compass Realty
Source: FLKMLS, MLS#603547

Home Details for 1009 Windsor Ln

Interior Features

Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3360 Square Feet
Appliances & Utilities
Appliances: Refrigerator, Oven, MicrowaveMicrowaveRefrigerator
Heating & Cooling
Has CoolingAir Conditioning: Central Air
Fireplace & Spa
Spa: HeatedHas a Spa
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: DeckHas a Private Pool
Parking & Garage
No Attached GarageHas Open ParkingParking: Open
Pool
Pool: In GroundPool
Frontage
Not on Waterfront

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Frame
Property Information
Parcel Number: 00030100000000

Price & Status

Price
List Price: $3,347,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Key WestCommunity: Tropical Sub (1.0)

Building

Building Area
Building Area: 3360 Square Feet

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 5662.8 sqft

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 603547

Price and Tax history

DateEventPrice
Feb 2, 2024
Source: FLKMLS #603547
Sold
$3,250,000
Nov 29, 2023
Source: FLKMLS #603547
Contingent
$3,347,000
Oct 13, 2023
Source: FLKMLS #603547
PendingToActive
$3,347,000
Sep 8, 2023
Source: FLKMLS #603547
Contingent
$3,347,000
Jan 24, 2023
Source: FLKMLS #603547
PriceChange
$3,347,000
Price decreased by 3%

Market trends in Key West

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.14M
$143K
MoM
Sale-to-List Price
โ€”
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 consumersโ€™ 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 1009 Windsor Ln

  • What is 1009 Windsor Ln estimated to be worth?
    Trulia's estimated value for 1009 Windsor Ln in Key West, FL is $3,601,900.
  • What is the price history for 1009 Windsor Ln?
    1009 Windsor Ln in Key West, FL last sold for $3,250,000 in February 2024.
  • 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 1009 Windsor Ln have air conditioning?
    Yes, 1009 Windsor Ln in Key West, FL has air conditioning.
  • Does 1009 Windsor Ln have a pool?
    Yes, 1009 Windsor Ln in Key West, FL has a pool.

Explore by feature - Pet Friendly

Explore by feature - Garage

Explore by feature - Air Conditioning

Explore by feature - Pool

Explore by feature - Washer/dryer

Explore by feature - Outdoor Space

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 1009 Windsor Ln

Skip to last item
Skip to first item

Homes for sale near 1009 Windsor Ln

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item