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1014 Flagler Avenue
Key West FL 33040 US

$4,995,000

Active Listing ID 618577
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3 bed
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4.00 Bath (3 Full , 1 Half)
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Lot: 0.27 Acres
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Single Family Residence

$4,995,000

Active Listing ID 618577
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1014 Flagler Avenue Some homes are built; others are authored. This is one of the latter-an architectural landmark shaped by David Wolkowsky, whose vision helped define Key West itself, with architecture by award-winning architect Rob Delaune that thoughtfully carries that legacy forward. This three-bedroom, three-and-a-half-bath estate, built in 1999 and comprehensively updated from the ground up, has been meticulously restored to museum-level standards with all-new systems, impact-rated windows and doors, and 10-foot doors and sliders throughout. The dramatic main living space is defined by soaring 22-foot ceilings, refinished custom teak columns and doors, expansive walls of glass, and a striking floor-to-ceiling built-in bookcase spanning the full height and length of the living room wall, complete with a concealed automatic disappearing television, while a thoughtfully designed chef's kitchen anchors the home with both beauty and functionality for everyday living and entertaining. Set on a rare, fully walled corner double lot spanning more than 11, 700 square feet, the property is enveloped by indigenous and exotic landscaping and hardscape design by Craig Reynolds Landscape Architecture, creating a private, resort-style environment centered around an oversized 40' x 20' custom heated swimming pool and generous outdoor living areas-an extraordinary sense of scale and seclusion in the heart of Casa Marina. The main residence offers two bedrooms and two-and-a-half bathrooms, complemented by a separate one-bedroom, one-bath guest house with its own kitchen, washer and dryer, and private garden, providing ideal accommodations for guests, extended family, or additional flexibility, all located on one of the most desirable blocks in one of Key West's premier neighborhoods, where privacy, scale, architectural pedigree, and legacy converge.

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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: 1
  • Cooling System: Window Unit(s), Wall/Window Unit(s), Central Air
  • Exterior Finish: Detached Guest Qtrs, Rain Gutters, Lighting, Privacy Wall/Fence, Sprinkler System, Water Display
  • Roof Type: Metal
  • Additional Features
  • Patio
  • Pool

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 4995000
  • unparsedaddress: 1014 Flagler Avenue
  • postalcity: Key West
  • stateorprovince: FL
  • country: US
  • postalcode: 33040
  • bathroomsfull: 3
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.2693
  • lotsizeunits: Acres
  • lotsizearea: 0.2693
  • livingarea: 3104
  • livingareaunits: Square Feet
  • latitude: 24.549132
  • longitude: -81.788857
  • listagentfullname: Team Kaufelt
  • listagentemail: teamkaufelt@trumanandcompany.com
  • listagentkey: 3yd-KWARFL-20200102150024995011000000
  • listagentmlsid: kwa.teamkaufelt
  • listagentpreferredphone: 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: 1998
  • listingcontractdate: 2026-02-10
  • listagenturl: http://www.teamkaufelt.com
  • countyorparish: Monroe
  • parcelnumber: 00058260-000000
  • appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s)
  • cooling: Window Unit(s), Wall/Window Unit(s), Central Air
  • constructionmaterials: CBS
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 1
  • parkingtotal: 0
  • parkingfeatures: Off Street
  • roof: Metal
  • view: Water
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Built-in Cabinets, Sky Light(s), Walk-in Closet(s), Tray Ceilings
  • exteriorfeatures: Detached Guest Qtrs, Rain Gutters, Lighting, Privacy Wall/Fence, Sprinkler System, Water Display
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bedroom 3, Bathroom 3, Bathroom 2, Bedroom 2, Bedroom 1, Bathroom 4
  • utilities: Cable Available
  • patioandporchfeatures: Porch, Patio
  • accessibilityfeatures: Accessible Approach with Ramp
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Privacy
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.78886, 24.549131
  • 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://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":"20070803221359772367000000", "ListOfficeCity":"Key West", "ListOfficeCountry":"US", "ListOfficeEmail":"inquiry@trumanandcompany.com", "ListOfficePostalCode":"33040", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Other - Key West, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/1014-Flagler-Ave_Key-West_FL_33040_M93681-64671?f=listhub&s=KWARFL&m=618577&c=rexren", "MLSModificationTimestamp":"2026-05-14 16:25:02", "Neighborhoods":[{"Description":null, "Name":"Martello Towers (1.0)"}], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":28772, "TaxDescription":"KW MARTELLO TOWERS PB1-140 LOTS 1-2-3-4 AND PT LOTS 20 AND 21 SQ 2 TR 27 G31-441/444 OR470-742D/C OR1009-253(AFFD) OR10", "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 5/21/2026 11:17:23 PM GMT
Source Updated Date: 7/3/2026 12:50:12 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.