744 Windsor Ln
Key West, FL 33040
Old Town- 6 Beds
- 7 Baths
- 5,632 sqft
6 Beds
7 Baths
5,632 sqft
Local Information
-- mins to
Description
From bodega to bodacious - two historic homes have been joined to create an unforgettable blend of vintage charm and contemporary luxury. Spacious gathering room opens into chef's kitchen and dining areas with walls of windows with garden views. The step-down living room has a picture perfect perspective of the resort-style tropical garden designed by Craig Reynolds with 40' X 18' heated pool. The lanai includes seating area, dining, outdoor kitchen, and cabana bath. Sophisticated master suite with sitting area and huge en-suite with soaking tub which opens to the rooftop deck. There is a second master suite in the west wing with equally compelling garden views.
Home Highlights
Parking
No Info
Outdoor
Porch, Patio, Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 744 Windsor Ln
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Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Interior Details Types of Rooms: Walk In ClosetCeiling Fan |
Appliances & Utilities Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher |
Levels, Entrance, & Accessibility Floors: Tile, Hardwood |
Security Security System |
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Exterior Home Features Roof: MetalDeckExterior: OtherFoundation Type: ConcretePatioPorchSprinkler System |
Pool Pool |
Parking & Garage Parking Spaces: 2Parking: Off Street |
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Year Built Year Built: 1933Year Updated: 2004 |
Property Type / Style Property Type: Single Family HomeArchitecture: Other |
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Furnished |
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Units in Building: 1 |
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Lot Area: 13 sqft |
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Community rooms Fitness Center |
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IntercomOn Site Laundry Available |
Price History for 744 Windsor Ln
| Date | Price | Event | Source |
|---|---|---|---|
| 03/02/2020 | $4,700,000 | Sold | FLKMLS #584145 |
| 09/09/2019 | $5,000,000 | PriceChange | Agent Provided |
| 08/28/2019 | $4,999,000 | PriceChange | Agent Provided |
| 04/18/2019 | $5,499,000 | PriceChange | Agent Provided |
| 02/06/2019 | $5,750,000 | Listed For Sale | Agent Provided |
| 06/23/2016 | $3,675,000 | Sold | FLKMLS #122429 |
| 05/10/2016 | $3,999,000 | Pending | Agent Provided |
| 03/09/2016 | $3,999,000 | PriceChange | Agent Provided |
| 02/15/2016 | $4,345,000 | PriceChange | Agent Provided |
| 11/23/2015 | $4,895,000 | Listed For Sale | Agent Provided |
| 07/18/2015 | $4,245,000 | ListingRemoved | Agent Provided |
| 06/27/2015 | $4,245,000 | PriceChange | Agent Provided |
| 04/29/2015 | $3,995,000 | PriceChange | Agent Provided |
| 04/18/2015 | $4,245,000 | PriceChange | Agent Provided |
| 03/04/2015 | $3,995,000 | PriceChange | Agent Provided |
| 10/03/2014 | $4,495,000 | Listed For Sale | Agent Provided |
| 04/17/2006 | $2,260,000 | Sold | N/A |
| 12/13/2001 | $1,800,000 | Sold | N/A |
| 07/09/1997 | $195,000 | Sold | N/A |
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 | $50,041 |
| Assessment | $6,408,336 |
Home facts updated by county records
Comparable Sales for 744 Windsor Ln
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.40 | Single-Family Home | $5,745,000 | 03/26/26 | 6 | 6.5 | 3,443 | |
0.35 | Single-Family Home | $4,225,000 | 03/16/26 | 5 | 5.5 | 3,434 | |
0.24 | Single-Family Home | $3,422,500 | 03/12/26 | 5 | 5.5 | 3,006 | |
0.35 | Single-Family Home | $3,300,000 | 05/21/26 | 5 | 6 | 3,667 | |
0.33 | Single-Family Home | $3,500,000 | 08/08/25 | 6 | 5 | 3,171 | |
0.31 | Single-Family Home | $4,425,000 | 05/26/26 | 4 | 4.5 | 3,336 | |
0.26 | Single-Family Home | $4,700,000 | 04/30/26 | 4 | 3.5 | 3,026 | |
0.31 | Single-Family Home | $2,750,000 | 06/29/26 | 5 | 4.5 | 2,721 | |
0.24 | Single-Family Home | $6,500,000 | 06/17/26 | 11 | 11 | 3,034 | |
0.22 | Single-Family Home | $3,750,000 | 10/20/25 | 4 | 3 | 2,173 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 744 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.
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