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1028 Flagler Avenue
Key West FL 33040 US

$4,650,000

Active Listing ID 621710
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4 bed
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3,589 square feet
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4.00 Bath (3 Full , 2 Half)
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Lot: 0.27 Acres
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Single Family Residence

$4,650,000

Active Listing ID 621710
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1028 Flagler Avenue A CASA MARINA ORIGINAL. Some houses capture a moment in time. Others seem to have understood, from the beginning, what makes Key West such an extraordinary place to live. Built in 1958, 1028 Flagler Avenue is a striking example of tropical mid-century modern architecture, set within a private three-building compound on 11, 586 square feet in Casa Marina, one of the island's most distinguished neighborhoods. Behind substantial privacy walls lies a world of its own. Winding pathways lead through lush native and tropical gardens that seem borrowed from a movie, connecting the main residence, separate two-bedroom guest quarters, and detached garage/workshop. Mature palms, flowering gardens, shaded terraces, and a custom swimming pool create an extraordinary sense of seclusion. Inside, clean architectural lines, high ceilings, and generous proportions celebrate indoor-outdoor living. Expansive living and dining areas, a library, and a separate study offer room to gather or retreat. Impact-rated windows and doors provide modern peace of mind without sacrificing the home's character. The guest quarters include their own living area and kitchen, ideal for family and visitors. Together, the three buildings offer 3, 589 square feet of combined enclosed space: 3, 173 square feet of living area plus a 416-square-foot garage/workshop. Covered outdoor dining, an outdoor kitchen, and abundant off-street parking make this compound as practical as it is beautiful. Just two blocks from Higgs Beach and the Atlantic Ocean, with White Street Pier, waterfront parks, tennis, pickleball, and some of Key West's best-loved restaurants close at hand. Old Town is minutes away, yet the privacy and tranquility of Casa Marina remain entirely your own.

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Property Features

  • Facts
  • Lot Size: 0.27 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • 1/2 Bathrooms: 2
  • Cooling System: Central Air
  • Exterior Finish: Fruit Tree(s), Lighting, Lanai, Outdoor Shower, Privacy Wall/Fence, Sprinkler System
  • Floor Covering: Tile
  • Roof Type: Metal
  • Additional Features
  • Patio
  • Pool

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 4650000
  • unparsedaddress: 1028 Flagler Avenue
  • postalcity: Key West
  • stateorprovince: FL
  • country: US
  • postalcode: 33040
  • bathroomsfull: 3
  • bathroomshalf: 2
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.266
  • lotsizeunits: Acres
  • lotsizearea: 0.266
  • livingarea: 3589
  • livingareaunits: Square Feet
  • latitude: 24.549546
  • longitude: -81.788204
  • listagentfullname: Team Kaufelt
  • listagentemail: teamkaufelt@trumanandcompany.com
  • listagentkey: 3yd-KWARFL-20200102150024995011000000
  • listagentmlsid: kwa.teamkaufelt
  • listagentpreferredphone: 3053931267
  • listagentofficephone: 3053931267
  • 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: 1958
  • listingcontractdate: 2026-10-20
  • listagenturl: http://www.teamkaufelt.com
  • countyorparish: Monroe
  • parcelnumber: 00058290000000
  • appliances: Washer, Dryer, Dishwasher, Refrigerator, Oven, Disposal, Freezer, Gas Appliances
  • cooling: Central Air
  • constructionmaterials: CBS
  • flooring: Tile
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Open
  • roof: Metal
  • view: Water
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Sky Light(s)
  • exteriorfeatures: Fruit Tree(s), Lighting, Lanai, Outdoor Shower, Privacy Wall/Fence, Sprinkler System
  • rooms: Bathroom 1, Bedroom 4, Bathroom 4, Bedroom 1, Bedroom 2, Bathroom 5, Bathroom 3, Bedroom 3, Bathroom 2
  • patioandporchfeatures: Porch
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Privacy
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.7882, 24.549545
  • 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":"teamkaufelt@trumanandcompany.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/1028-Flagler-Ave_Key-West_FL_33040_M63448-89750?f=listhub&s=KWARFL&m=621710&c=rexren", "MLSModificationTimestamp":"2026-10-20 16:05:32", "Neighborhoods":[{"Description":null, "Name":"Martello Towers (1.0)"}], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":24852, "TaxDescription":"Kw Martello Towers Pb1-140 Lots 11-12-13-14 Sqr 2 Tr 27 Or262-233/234 Or629-263/264 Or1122-217 Or1164-1319 Or1392-1475/6", "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/25/2026 3:33:15 AM GMT
Source Updated Date: 10/24/2026 10:55:23 AM GMT

Courtesy of: Team Kaufelt, Truman & Co. (KW), teamkaufelt@trumanandcompany.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.