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1014 Flagler Avenue
Key West FL 33040 US

$4,700,000

Active Listing ID 618577
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3 bed
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3,104 square feet
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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

$4,700,000

Active Listing ID 618577
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1014 Flagler Avenue A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11, 730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3, 104 square feet. 11, 730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

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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: Wall/Window Unit(s), Central Air, Window Unit(s)
  • 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: 4700000
  • 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: Wall/Window Unit(s), Central Air, Window Unit(s)
  • constructionmaterials: CBS
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • 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 3, Bedroom 2, Bedroom 1, Bathroom 1, Bathroom 2, Bedroom 3, Bathroom 4
  • utilities: Cable Available
  • patioandporchfeatures: Patio, Porch
  • 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://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/1014-Flagler-Ave_Key-West_FL_33040_M93681-64671?f=listhub&s=KWARFL&m=618577&c=rexren", "MLSModificationTimestamp":"2026-10-01 14:07:04", "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: 10/3/2026 3:15:34 AM GMT
Source Updated Date: 10/6/2026 12:47:03 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.