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Sold for $4,500,000
  • $4,500,000

    314 Simonton St, Key West, FL 33040

    8beds
    8,472sqft
    Multi Family
    Built in 1921
    -- sqft lot
    $4,515,100 Zestimate®
    $531/sqft
    $3,174 Estimated rent

    Home value

    $4,515,100

    $4.02M - $5.06M

    $3,174/mo

    Zestimate® history
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    $3,174/mo

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    $27,126/mo

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    $27,126/mo

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    What's special

    Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Don't miss the chance to own a piece of Key West's past while shaping its future with this truly one-of-a-kind property.

    Zillow last checked:

    Listing updated:

    Listed by:

    Team Gardner/Langley 305-902-2447,

    Berkshire Hathaway HomeServices Knight & Gardner Realty

    Bought with:

    Berkshire Hathaway HomeServices Knight & Gardner Realty

    Source: FLKMLS,MLS#: 612250MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 8
    • Bathrooms: 11
    • Full bathrooms: 7
    • 1/2 bathrooms: 4
    Interior area
    • Total structure area: 8,472
    • Total interior livable area: 8,472 sqft

    Property

    Features
    • Has private pool: Yes
    • Pool features: In Ground, Concrete
    Lot
    • Size: 7,840 Square Feet
    Details
    • Parcel number: 00004210000000
    • Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med

    Construction

    Type & style
    • Home type: MultiFamily
    • Architectural style: Other
    • Property subtype: Multi Family
    Materials
    • Combo Construction
    Condition
    • Year built: 1921

    Community & HOA

    Community
    • Subdivision: Old Town - Unlisted (1.0)
    HOA
    • Has HOA: No
    • Services included: None
    Location
    • Region: Key West

    Financial & listing details

    • Price per square foot: $531/sqft
    • Annual tax amount: $13,667
    • Date on market: 11/14/2024

    Price history

    DateEventPrice
    7/6/2026Sold$4,500,000-9.1%$531/sqft
    Source: FLKMLS #612250 Report a problem
    4/28/2026Contingent$4,950,000$584/sqft
    Source: FLKMLS #612250 Report a problem
    4/25/2026Price change$4,950,000-5.7%$584/sqft
    Source: Key West AOR #612250 Report a problem
    1/12/2026Price change$5,250,000-4.5%$620/sqft
    Source: Key West AOR #612250 Report a problem
    7/28/2025Price change$5,500,000-6.8%$649/sqft
    Source: FLKMLS #612250 Report a problem
    5/20/2025Price change$5,900,000-7.8%$696/sqft
    Source: FLKMLS #612250 Report a problem
    4/1/2025Price change$6,400,000-7.2%$755/sqft
    Source: Key West AOR #612250 Report a problem
    11/14/2024Listed for sale$6,900,000$814/sqft
    Source: Key West AOR #612250 Report a problem

    Public tax history

    Tax history is unavailable.

    Neighborhood: Historic Seaport

    Nearby schools

    GreatSchools rating
    Get a cash offer in 3 minutes
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    Estimated market value
    $4,515,100
    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
    $4,515,100