$1,175,000
$220K PRICE DROP

Estimated payment $7,032/month

Total Views 16,926
2 Beds
1 Bath
723 Sq Ft
$1,625 Price per Sq Ft

About This Home

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.

Listing Agent

Amber DeBevec

LoKation Real Estate License #3484789 Listed on: 05/24/2025

LoKation Real Estate

Map

Home Details

Home Type

Single Family

Est. Annual Taxes

$10,137

Year Built

1928

Lot Details

0

Listing Details

  • Property Type: Residential
  • Style: Single Family
  • As Is Right To Inspect: Yes
  • First Right of Refusal: No
  • Mandatory HOA: No
  • Fee Includes: None
  • Key Island: Key West
  • K W Neighborhood: Old Town-N of Truman
  • Limited Representation: No
  • Marathon Neighborhood: N/A
  • Mile Marker: 1.00
  • Min Rental Days: 28.00
  • M L S Identifier: 20060123165453488875000000
  • Pets: Pets Allowed
  • Property Group I D: 19990816212109142258000000
  • Side: Median
  • State Province: FL
  • Taxes: 10361.58
  • Title: Negotiable
  • Vehicle Storage: Carport, Trailer Storage, Off Street Parking
  • Year Built: 1928
  • Alternate Key Number: 1019445
  • Building Style: Conch
  • Cooling Heating: Ceiling Fans(s), Ductless
  • Lot Sq Ft: 2992.00
  • Porch Balcony: Open Porch/Balcony, Patio
  • Shutters: Panel
  • Tax Exemptions: Homestead
  • Building Style Above Flood: Yes
  • Building Style Stories: 1 Story
  • Estimated Living Sq Ft: 723.00
  • Sewer Hook Up: Yes
  • Statistical Purposes Only: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Interior Amenities: Dade County Pine, Quartz Countertops, Storage
  • Total Bathrooms: 1.00
  • Full Bathrooms: 1
  • Appliances: Washer, Stainless Steel Appliance(s), Microwave, Range, Refrigerator, Dishwasher, Dryer
  • Floor: Tile, Wood
  • Windows/Doors: Wood Windows, Impact Rstnce Doors
  • Total Bedrooms: 2

Exterior Features

  • Dockage: None
  • Waterfront: None
  • Waterfront: No
  • Construction: Frame
  • Exterior Features: Fencing, Storage, Shed, Privacy Wall/Fence, Detached Guest Qtrs
  • Roof: Metal Roof
  • Waterview: No Waterview
  • Pool: No

Utilities

  • Utilities: FKAA, Cable Available, Municipal Sewer

Lot Info

  • Deed Restrictions: Unknown
  • Flood Zone: AE
  • Parcel Number: 00018790-000000
  • Land Size: Less Than 1/4 Acre
  • Acres: 0.07

Rental Info

  • Rentals Allowed: With Restrictions
  • Furnished: Negotiable

Tax Info

  • Tax Year: 2024

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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Average Value
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $10,137 $1,246,417 -- --
2023 $10,137 $1,202,793 $1,110,780 $92,013
2022 $6,266 $802,912 $710,899 $92,013
2021 $4,059 $439,661 $0 $0
2020 $3,763 $407,578 $0 $0
2019 $3,628 $389,122 $0 $0
2018 $3,474 $365,022 $0 $0
2017 $3,524 $364,422 $0 $0
2016 $3,789 $389,023 $0 $0
2015 $3,858 $385,811 $0 $0
2014 $2,718 $278,912 $0 $0
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
11/19/2025 11/19/25 Price Changed $1,175,000 -1.7% $1,625 / Sq Ft
08/23/2025 08/23/25 Price Changed $1,195,000 -14.3% $1,653 / Sq Ft
05/24/2025 05/24/25 For Sale $1,395,000 -- $1,929 / Sq Ft
Source: Key West Association of REALTORS®

Purchase History

Date Type Sale Price Title Company
Interfamily Deed Transfer -- Attorney
Deed $8,000 --
Source: Public Records

Source: Key West Association of REALTORS®

MLS Number: 615169

Key West Association of REALTORS®

APN: 00018790-000000