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720D Simonton Street
Key West FL 33040 US

$4,990,000

Active Listing ID 618363
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4 bed
bath icon
4.00 Bath (4 Full)
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Single Family Residence

$4,990,000

Active Listing ID 618363
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720D Simonton Street KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5, 220sf lot, this 2, 441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.

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Property Features

  • Facts
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • Cooling System: Ceiling Fan(s)
  • Exterior Finish: Detached Guest Qtrs, Water Display, Storage, Privacy Wall/Fence, Outdoor Shower, Lighting
  • Floor Covering: Tile, Wood
  • Roof Type: Metal

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 4990000
  • unparsedaddress: 720D Simonton Street
  • postalcity: Key West
  • stateorprovince: FL
  • country: US
  • postalcode: 33040
  • bathroomsfull: 4
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeunits: Acres
  • livingarea: 2441
  • livingareaunits: Square Feet
  • latitude: 24.55389
  • longitude: -81.799736
  • listagentfullname: The Spottswood Team
  • listagentemail: everyone@thespottswoodteam.com
  • listagentkey: 3yd-KWARFL-20250916203935531640000000
  • listagentmlsid: 20250916203935531640000000
  • listagentpreferredphone: 3054324848
  • listagentofficephone: 3052922244
  • listofficekey: 3yd-KWARFL-20070803221359772367000000
  • listofficemlsid: 20070803221359772367000000
  • 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: 2008
  • listagenturl: http://www.trumanandcompany.com
  • countyorparish: Monroe
  • appliances: Dishwasher, Dryer, Freezer, Microwave, Range, Refrigerator, Washer
  • cooling: Ceiling Fan(s)
  • constructionmaterials: Concrete
  • flooring: Tile, Wood
  • numberofunitstotal: 2
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • roof: Metal
  • view: Water
  • waterfrontyn: False
  • interiorfeatures: Drapes/Blinds Incl, Window Treatments, Walk-in Closet(s), Storage, Built-in Cabinets, Pantry
  • exteriorfeatures: Detached Guest Qtrs, Water Display, Storage, Privacy Wall/Fence, Outdoor Shower, Lighting
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4
  • otherstructures: Storage
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • fencing: Fenced, Privacy
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.799736, 24.55389
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Truman & Co. Real Estate Services", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"everyone@thespottswoodteam.com", "ListBrokerageCity":"Key West", "ListBrokerageCountry":"US", "ListBrokerageEmail":"terri@terrispottswood.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/KWARFL/3cb3c48183e111e19b52123138048d21/20150318142929328.png", "ListBrokerageName":"Truman & Co. Real Estate Services", "ListBrokeragePhone":"(305) 292-2244", "ListBrokeragePostalCode":"33040", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"1205 Truman Avenue", "ListBrokerageWebsiteUrl":"http://www.trumanandcompany.com", "ListOfficeAddress1":"1205 Truman Avenue", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"20080326130947521052000000", "ListOfficeCity":"Key West", "ListOfficeCountry":"US", "ListOfficeEmail":"inquiry@trumanandcompany.com", "ListOfficePostalCode":"33040", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential - Single Family - Key West, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/720D-Simonton-St_Key-West_FL_33040_M52920-71843?f=listhub&s=KWARFL&m=618363&c=rexren", "MLSModificationTimestamp":"2026-02-03T09:47:09Z", "Neighborhoods":[{"Description":null, "Name":"02 - Key West"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":31381, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 2/3/2026 5:09:19 PM GMT
Source Updated Date: 2/4/2026 12:52:35 PM GMT

Courtesy of: The Spottswood Team, Truman & Co. (KW), everyone@thespottswoodteam.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.