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421 - 423 Simonton Street Key West FL 33040US6 Bed, 8.00 Bath (6 Full Bath , 2 Half Bath), 614546
421 - 423 Simonton Street Key WestFL33040
5850000.0000 1/1/1900 12:00:00 AM
Realty Executives Florida Keys (New Town)
3706 N Roosevelt Blvd. , Suite 208 Upper FloorKey WestFL33040
305-501-4229
1 /

Courtesy of: Will Langley, Berkshire Hathaway HomeServices Knight & Gardner Realty, will@keysrealestate.com

421 - 423 Simonton Street
Key West FL 33040 US

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1 /

Courtesy of: Will Langley, Berkshire Hathaway HomeServices Knight & Gardner Realty, will@keysrealestate.com

Realty Executives Florida Keys (New Town)
3706 N Roosevelt Blvd. , Suite 208 Upper Floor
Key West, FL, US 33040
305-501-4229

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421 - 423 Simonton Street
Key West FL 33040 US

$5,850,000

Active Listing ID 614546
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6 bed
bath icon
8.00 Bath (6 Full , 2 Half)
lot icon
Lot: 0.08 Acres
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Multi Family

$5,850,000

Active Listing ID 614546
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Maps

421 - 423 Simonton Street Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool--perfect for cooling off after a day in the sun or enjoying a quiet evening under the palms.Whether you're looking for a investment opportunity, a vacation retreat with rental flexibility, or a mix of both, this unique setup delivers unmatched versatility just steps from the vibrant restaurants, galleries, and nightlife of Duval Street.

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Property Features

  • Facts
  • Lot Size: 0.08 Acres
  • Property Type: Residential Multi Family
  • Property Sub-type: Multi Family
  • Features
  • Full Bathrooms: 6
  • 1/2 Bathrooms: 2
  • Cooling System: Ceiling Fan(s)
  • Exterior Finish: Privacy Wall/Fence
  • Roof Type: Metal

Property

  • propertytype: Residential Multi Family
  • propertysubtype: Multi Family
  • listprice: 5850000
  • unparsedaddress: 421 - 423 Simonton Street
  • postalcity: Key West
  • stateorprovince: FL
  • country: US
  • postalcode: 33040
  • bathroomsfull: 6
  • bathroomshalf: 2
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.08
  • lotsizeunits: Acres
  • lotsizearea: 0.08
  • livingarea: 3010
  • livingareaunits: Square Feet
  • latitude: 24.557125
  • longitude: -81.801587
  • listagentfullname: Will Langley
  • listagentemail: will@keysrealestate.com
  • listagentkey: 3yd-KWARFL-20110223211150165049000000
  • listagentmlsid: 20110223211150165049000000
  • listagentpreferredphone: 3052945155
  • listagentofficephone: 3052945155
  • listofficekey: 3yd-KWARFL-20070803221344494963000000
  • listagentstatelicense: 3242135
  • listofficemlsid: 20070803221344494963000000
  • disclaimer: Copyright © 2025 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: 2020
  • listagenturl: http://www.will-langley.com
  • countyorparish: Monroe
  • parcelnumber: 00006360-000000
  • appliances: Dryer, Microwave, Range, Refrigerator
  • cooling: Ceiling Fan(s)
  • numberofunitstotal: 2
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • roof: Metal
  • view: Water
  • waterfrontyn: False
  • franchiseaffiliation: Berkshire Hathaway HomeServices
  • interiorfeatures: Built-in Cabinets, Smoke Alarms
  • exteriorfeatures: Privacy Wall/Fence
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • fencing: Fenced, Privacy
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.80159, 24.557125
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Berkshire Hathaway Keys Real Estate | Knight & Gardner Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"susan@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":"20110223211150165049000000", "ListOfficeCity":"Key West", "ListOfficeCountry":"US", "ListOfficeEmail":"info@keysrealestate.com", "ListOfficePostalCode":"33040", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Multi-family - Key West, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/421-Simonton-St_Key-West_FL_33040_M55178-53474?f=listhub&s=KWARFL&m=614546&c=rexren", "MLSModificationTimestamp":"2025-12-09T13:04:55Z", "Neighborhoods":[{"Description":null, "Name":"02 - Key West"}], "PostalCode":null, "RawPropertySubType":"Multi-family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":26522.53, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 12/9/2025 9:06:42 PM GMT
Source Updated Date: 12/30/2025 7:20:07 PM GMT

Courtesy of: Will Langley, Berkshire Hathaway HomeServices Knight & Gardner Realty, will@keysrealestate.com

Copyright © 2025 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.

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