729 Windsor Ln

723 Sq. Ft.
$1,314 / Sq. Ft.
723
Sq. Ft.
$1,314
per Sq. Ft.

Description

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...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.
  1. Listed by Amber DeBevec • LoKation Real Estate

Property Details for 729 Windsor Lane

Waterfront
None
Waterfront
No
Zoning
HMDR - Historic Medium Density Residential
Subdivision
William's Court (1.0)
Building Style
Shotgun
Vehicle Storage
Carport, Trailer Storage, Off Street Parking
Pets
Pets Allowed

Open Houses

Saturday, Feb 28th

11:00 AM - 1:00 PM

Public

LISTING UPDATED: 02/23/2026 02:33 PM

Property Details for 729 Windsor Lane

StatusContingent / Show
MLS #615169
Days on Market275
Taxes$10,362 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1928
Lot Size0.07 AC / 2,992 SF
CountyMonroe County

Location

Listing Courtesy of LoKation Real Estate
Add your commute

Building Information for 729 Windsor Lane

Stories1Year Built1928Building Size-Lot Size0.07 AC / 2,992 SF

Payment Calculator

$5,494 per month

30 year fixed, 6.15% Interest

Principal and Interest

$4,630

Property Taxes

$864

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 729 Windsor Lane

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.797714
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Negotiable
  • Tax Year: 2024
  • Tax Exemptions: Homestead
Property
Lot Information
  • Acres: 0.07
  • Parcel #: 00018790-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT OF TR 5 OR27-439/40 OR27-441/42 OR569-423/24 OR921-640/41 OR921-642 OR2694-1238 OR3159-1522 OR3269-2308
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 35
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Cable Available, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: No
  • Porch/Balcony: Open Porch/Balcony, Patio
Interior and Exterior Features
Interior Features
  • Floor: Tile, Wood
  • Interior Features: Dade County Pine, Quartz Countertops, Storage
  • Appliances: Washer, Stainless Steel Appliance(s), Microwave, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Shutters: Panel
  • Construction: Frame
  • Dockage: None
  • Exterior Features: Fencing, Storage, Shed, Privacy Wall/Fence, Detached Guest Qtrs
  • Windows/Doors: Wood Windows, Impact Rstnce Doors

Property History for 729 Windsor Lane

DateEvent & SourcePriceAppreciation
Feb 23, 2026

Backup Contract

FKMLS #615169

May 24, 2025

Price Change

FKMLS #615169

$1,395,000
May 24, 2025

Price Change

FKMLS #615169

$1,195,000
May 24, 2025

Price Change

FKMLS #615169

$1,175,000
May 24, 2025

Listed (Active)

FKMLS #615169

$950,000
Mar 19, 2018

Temp Off Market

FKMLS #574236

Feb 9, 2017

Listed (Active)

FKMLS #574236

$1,200,000
DateEvent & SourcePrice
02/23/2026

Backup Contract

FKMLS #615169

05/24/2025

Price Change

FKMLS #615169

$1,395,000
05/24/2025

Price Change

FKMLS #615169

$1,195,000
05/24/2025

Price Change

FKMLS #615169

$1,175,000
05/24/2025

Listed (Active)

FKMLS #615169

$950,000
03/19/2018

Temp Off Market

FKMLS #574236

02/09/2017

Listed (Active)

FKMLS #574236

$1,200,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 729 Windsor Lane

Taxable ValueLand$1,172,984Additions$103,473Total$1,276,457
Tax Record2024$10,362 ($863 / month)
Home Facts
Beds2Baths1Total Finished SqFt723 SqFtAbove Grade Finished SqFt723 SqFtStories1Lot Size2,725 SqFtStyleSingle Family ResidenceYear Built1928Year Renovated1989CountyMONROEAPN00018790-000000

Schools near 729 Windsor Lane

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Public - K to 5
Public - K to 12
Rating
School
Distance
Horace O'bryant School
PublicPK to 8

Key West High School
Public9 to 12

Monroe Virtual Instruction Program
PublicK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of LoKation Real Estate

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.