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For sale
  • Price cut: $400K (7/28)
    $5,500,000

    314 Simonton St, Key West, FL 33040

    8beds
    8,472sqft
    : 
    Multi Family
    Built in 1921
    -- sqft lot
    $-- Zestimate®
    $649/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.
    270 days
    on Zillow
    |
    4,153
    |
    224
    |

    Zillow last checked: 7 hours ago

    Listing updated: July 28, 2025 at 12:08am

    Listed by:

    Team Gardner/Langley 305-902-2447,

    Berkshire Hathaway HomeServices Knight & Gardner Realty

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

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 314 Simonton St.

    Next available tour time:Today at 11am

    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: 7,840.8 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: $649/sqft
    • Annual tax amount: $13,667
    • Date on market: 11/14/2024
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