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Under contract
  • Price cut: $300K (4/25)
    $4,950,000

    314 Simonton St, Key West, FL 33040

    8beds
    8,472sqft
    : 
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    Multi Family
    Built in 1921
    -- sqft lot
    $-- Zestimate®
    $584/sqft
    $-- HOA

    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.
    587 days
    |
    265
    |
    10
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Team Gardner/Langley 305-902-2447,

    Berkshire Hathaway HomeServices Knight & Gardner Realty

    Source: FLKMLS,MLS#: 612250MLS LogoOriginating MLS: Key West Association

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 8
      • Bathrooms: 11
      • Full bathrooms: 7
      • 1/2 bathrooms: 4
      Appliances
      • Included: YES
      Features
      • Doors: Sliding Glass Doors
      Interior area
      • Total interior livable area: 8,472 sqft

      Property

      Features
      • Levels: 3 Stories
      • Stories: 3
      • Has private pool: Yes
      • Pool features: In Ground, Concrete
      • Water view: None
      • Waterfront features: None, Dockage: None
      Lot
      • Size: 7,840 Square Feet
      • Features: Less Than 1/4 Acre
      Details
      • Parcel number: 00004210000000
      • Zoning: HNC
      • Zoning description: (1-3) Hist Nghborhd Comml 1 - 3 Coastal Med

      Construction

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

      Utilities & green energy

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

      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: $584/sqft
      • Annual tax amount: $13,667
      • Date on market: 11/14/2024

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $3,151/mo

        Price history

        DateEventPrice
        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.

        Monthly payment

        Est. payment

          Payment breakdown

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          All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
          HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
          Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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          Climate risks

          Neighborhood: Historic Seaport

          Getting around

          95 / 100
          Walker's Paradise
          28 / 100
          Some Transit
          92 / 100
          Biker's Paradise

          Nearby schools

          GreatSchools rating

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