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314 Simonton Street
Key West FL 33040 US

$4,950,000

Active Under Contract Listing ID 612134
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8 bed
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9.00 Bath (7 Full , 4 Half)
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Lot: 0.18 Acres
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Other

$4,950,000

Active Under Contract Listing ID 612134
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314 Simonton Street 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.

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Property Features

  • Facts
  • Lot Size: 0.18 Acres
  • Property Type: Commercial Sale
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 7
  • 1/2 Bathrooms: 4
  • Cooling System: Window Unit(s), Wall/Window Unit(s)
  • Floor Covering: Combo

Property

  • propertytype: Commercial Sale
  • propertysubtype: Other
  • listprice: 4950000
  • unparsedaddress: 314 Simonton Street
  • postalcity: Key West
  • stateorprovince: FL
  • country: US
  • postalcode: 33040
  • bathroomsfull: 7
  • bathroomshalf: 4
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.18
  • lotsizeunits: Acres
  • lotsizearea: 0.18
  • livingarea: 8472
  • livingareaunits: Square Feet
  • latitude: 24.558333
  • longitude: -81.803104
  • listagentfullname: Team Gardner/Langley
  • listagentemail: commercial@keysrealestate.com
  • listagentkey: 3yd-KWARFL-20080619155121704955000000
  • listagentmlsid: kwa.2032
  • listagentpreferredphone: 3059022447
  • listofficekey: 3yd-KWARFL-20070803221344494963000000
  • listofficemlsid: kwa.10017
  • disclaimer: Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: KWARFL
  • yearbuilt: 1921
  • listingcontractdate: 2024-11-05
  • listagenturl: http://www.keysrealestate.com
  • countyorparish: Monroe
  • parcelnumber: 00004210-000000
  • cooling: Window Unit(s), Wall/Window Unit(s)
  • constructionmaterials: Combo Construction
  • flooring: Combo
  • numberofunitstotal: 8
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 3
  • parkingtotal: 0
  • parkingfeatures: Off Street, Covered
  • view: Water
  • waterfrontyn: False
  • franchiseaffiliation: Berkshire Hathaway HomeServices
  • rooms: Bedroom 7, Bathroom 4, Bathroom 9, Bedroom 3, Bedroom 5, Bedroom 1, Bedroom 2, Bedroom 8, Bathroom 2, Bathroom 7, Bathroom 10, Bathroom 6, Bedroom 6, Bathroom 1, Bathroom 8, Bathroom 5, Bedroom 4, Bathroom 3, Bathroom 11
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.8031, 24.558332
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Berkshire Hathaway Keys Real Estate | Knight & Gardner Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"commercial@keysrealestate.com", "ListBrokerageCity":"Key West", "ListBrokerageCountry":"US", "ListBrokerageEmail":"info@keysrealestate.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/KWARFL/060114707e9011e1b78c12313904e194/20190802195037982.png", "ListBrokerageName":"Berkshire Hathaway Keys Real Estate | Knight & Gardner Realty", "ListBrokeragePhone":"(305) 294-5155", "ListBrokeragePostalCode":"33040", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"336 Duval St", "ListBrokerageWebsiteUrl":"http://www.keysrealestate.com", "ListOfficeAddress1":"336 Duval St. ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"20070803221344494963000000", "ListOfficeCity":"Key West", "ListOfficeCountry":"US", "ListOfficeEmail":"info@keysrealestate.com", "ListOfficePostalCode":"33040", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"COMMERCIAL - Key West, FL", "ListingURL":null, "MLSModificationTimestamp":"2026-04-28 19:33:28", "Neighborhoods":[{"Description":null, "Name":"Old Town - Unlisted (1.0)"}], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":13668, "TaxDescription":"KW PT LT 2 SQR 24 OR252-75/76 OR625-467/68 OR742-76 OR845-822 OR1648-526/27 OR2519-148/49 OR2852-2389/90", "TaxYear":"2023"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 5/21/2026 11:17:36 PM GMT
Source Updated Date: 5/26/2026 6:40:34 PM GMT

Courtesy of: Team Gardner/Langley, Berkshire Hathaway HomeServices Knight & Gardner Realty, commercial@keysrealestate.com

Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.