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Sold for $865,000
  • $865,000

    729 Windsor Ln, Key West, FL 33040

    2beds
    723sqft
    Single Family Residence
    Built in 1928
    3,049.2 Square Feet Lot
    $866,300 Zestimate®
    $1,196/sqft
    $3,699 Estimated rent

    Home value

    $866,300

    $762,000 - $988,000

    $3,699/mo

    Zestimate® history
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    What's special

    Contemporary cabinetryStylish tileworkUpdated fixturesThoughtfully updated interiorOff-street parkingSleek countertopsPrivate setting
    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Amber Debevec,

    LoKation Real Estate

    Bought with:

    Elaine S Coyle, 704304

    Keller Williams Key West Compass Realty

    Source: FLKMLS,MLS#: 615169MLS LogoOriginating MLS: Key West Association

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 2
    • Bathrooms: 1
    • Full bathrooms: 1
    Cooling
    • Ceiling Fans(s), Ductless
    Appliances
    • Included: Washer, Stainless Steel Appliance(s), Microwave, Range, Refrigerator, Dishwasher, Dryer
    Features
    • Dade County Pine, Quartz Countertops, Storage
    • Flooring: Tile, Wood
    • Doors: Impact Rstnce Doors
    • Windows: Wood Frames, Panel
    Interior area
    • Total interior livable area: 723 sqft

    Property

    Parking
    • Parking features: Carport, Trailer Storage, Off Street
    • Has carport: Yes
    Features
    • Levels: One
    • Stories: 1
    • Patio & porch: Open Porch/Balcony, Patio
    • Exterior features: Storage
    • Fencing: Fenced,Privacy
    • Water view: None
    • Waterfront features: None, Dockage: None
    Lot
    • Size: 3,049 sqft
    • Features: Less Than 1/4 Acre
    Details
    • Additional structures: Shed(s), Detached Guest Qtrs
    • Parcel number: 00018790000000
    • Zoning: HMDR
    • Zoning description: Historic Medium Density Residential

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Shotgun
    • Property subtype: Single Family Residence
    Materials
    • Frame
    • Roof: Metal
    Condition
    • Year built: 1928

    Utilities & green energy

    • Sewer: Municipal Sewer, Public Sewer
    • Utilities for property: FKAA, Cable Available

    Community & neighborhood

    Location
    • Region: Key West
    • Subdivision: William's Court (1.0)

    HOA & financial

    HOA
    • Has HOA: No
    • Services included: None

    Other

    Other facts
    • Listing terms: Cash,FHA,VA Loan,Conventional

    Price history

    DateEventPrice
    3/23/2026Sold$865,000-8.9%$1,196/sqft
    Source: FLKMLS #615169 Report a problem
    3/3/2026Pending sale$950,000$1,314/sqft
    Source: FLKMLS #615169 Report a problem
    2/23/2026Contingent$950,000$1,314/sqft
    Source: FLKMLS #615169 Report a problem
    1/12/2026Price change$950,000-19.1%$1,314/sqft
    Source: Key West AOR #615169 Report a problem
    11/19/2025Price change$1,175,000-1.7%$1,625/sqft
    Source: FLKMLS #615169 Report a problem
    8/23/2025Price change$1,195,000-14.3%$1,653/sqft
    Source: Key West AOR #615169 Report a problem
    5/24/2025Listed for sale$1,395,000+16.3%$1,929/sqft
    Source: FLKMLS #615169 Report a problem
    3/19/2018Listing removed$1,200,000$1,660/sqft
    Source: Ocean Sotheby's International Realty #574236 Report a problem
    7/11/2017Price change$1,200,000-6.6%$1,660/sqft
    Source: Engel & Volkers Key West #574236 Report a problem
    4/4/2017Price change$1,285,000-1.2%$1,777/sqft
    Source: Engel & Volkers Key West #574236 Report a problem
    2/12/2017Listed for sale$1,300,000$1,798/sqft
    Source: Engel & Voelkers Florida Keys (KW) #574236 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$10,681 +3.1%$1,276,457 +2.4%
    2024$10,362 +2.2%$1,246,417 +3.6%
    2023$10,137 +61.8%$1,202,793 +84.9%
    2022$6,266 +54.4%$650,403 +47.9%
    2021$4,059 +7.9%$439,661 +7.9%
    2020$3,763 $407,578 +4.7%
    2019$3,763 +3.7%$389,122 +6.6%
    2018$3,628 $365,022 +0.2%
    2017-- $364,422 -6.3%
    2016$3,524 -7%$389,023 +0.8%
    2015$3,789 $385,811

    Find assessor info on the county website

    Neighborhood: Old Town

    Nearby schools

    GreatSchools rating
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    Estimated market value
    $866,300
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $866,300