x
Showing 1 of 0
X
Save

720D Simonton Street
Key West FL 33040 US

$4,950,000

Active Listing ID 621632
bed icon
4 bed
rule icon
2,441 square feet
bath icon
4.00 Bath (4 Full)
lot icon
Lot: 0.12 Acres
home icon
Single Family Residence

$4,950,000

Active Listing ID 621632
Save

720D Simonton Street DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY 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.

Collapse all

Property Features

  • Facts
  • Lot Size: 0.12 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • Cooling System: Central Air
  • Exterior Finish: Detached Guest Qtrs, Lighting, Outdoor Shower, Privacy Wall/Fence, Storage, Water Display
  • Floor Covering: Wood, Tile
  • Roof Type: Metal
  • Additional Features
  • Patio
  • Pool

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 4950000
  • unparsedaddress: 720D Simonton Street
  • postalcity: Key West
  • stateorprovince: FL
  • country: US
  • postalcode: 33040
  • bathroomsfull: 4
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.1198
  • lotsizeunits: Acres
  • lotsizearea: 0.1198
  • livingarea: 2441
  • livingareaunits: Square Feet
  • latitude: 24.55389
  • longitude: -81.799736
  • listagentfullname: The Spottswood Team
  • listagentemail: everyone@thespottswoodteam.com
  • listagentkey: 3yd-KWARFL-20250916203935531640000000
  • listagentmlsid: kwa.thespottswoodteam
  • listagentpreferredphone: 3054324848
  • listagentofficephone: 3054324848
  • listofficekey: 3yd-KWARFL-20070803221359772367000000
  • listofficemlsid: kwa.10208
  • 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
  • listingcontractdate: 2026-10-14
  • listagenturl: http://www.trumanandcompany.com
  • countyorparish: Monroe
  • appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Microwave, Freezer, Wine Cooler
  • cooling: Central Air
  • constructionmaterials: CBS, Concrete, Combo Construction
  • flooring: Wood, Tile
  • numberofunitstotal: 2
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Off Street
  • roof: Metal
  • view: Water
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Built-in Cabinets, Storage, Walk-in Closet(s)
  • exteriorfeatures: Detached Guest Qtrs, Lighting, Outdoor Shower, Privacy Wall/Fence, Storage, Water Display
  • rooms: Bedroom 3, Bathroom 3, Bathroom 1, Bedroom 4, Bathroom 4, Bathroom 2, Bedroom 2, Bedroom 1
  • otherstructures: Storage
  • patioandporchfeatures: Porch, Patio
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: 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, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"everyone@thespottswoodteam.com", "ListBrokerageCity":"Key West", "ListBrokerageCountry":"US", "ListBrokerageEmail":"terri@terrispottswood.com", "ListBrokerageLogoUrl":"http://lh.rdcpix.com/3cb3c48183e111e19b52123138048d21k-c739538518r.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":"20070803221359772367000000", "ListOfficeCity":"Key West", "ListOfficeCountry":"US", "ListOfficeEmail":"inquiry@trumanandcompany.com", "ListOfficePostalCode":"33040", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential, Key West, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/720D-Simonton-St_Key-West_FL_33040_M52920-71843?f=listhub&s=KWARFL&m=621632&c=rexren", "MLSModificationTimestamp":"2026-10-14 21:38:17", "Neighborhoods":[{"Description":null, "Name":"Old Town - Unlisted (1.0)"}], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":32510, "TaxDescription":"KW PT LOT 3 SQR 2 TR 4 OR172-109/10 OR190-476/77 OR333-396/97 OR610-518/19", "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/14/2026 9:42:08 PM GMT
Source Updated Date: 10/16/2026 12:52:22 AM 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.