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2309 Flagler Avenue
Key West FL 33040 US

$1,195,000

Active Listing ID 619530
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3 bed
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2.00 Bath (2 Full)
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Lot: 0.17 Acres
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Single Family Residence

$1,195,000

Active Listing ID 619530
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2309 Flagler Avenue Midtown Jewel on Flagler Avenue! This lovely Mid-century modern home is nestled within a private tropical oasis on an oversized 7, 500 sq. ft. lot, offering the perfect blend of architectural character and serene island living. Expansive glass walls and approximately 64 feet of floor-to-ceiling sliders and windows create a greenhouse-like ambiance, filling the home with natural light and showcasing breathtaking views of the lush, mature gardens from nearly every room.The thoughtfully designed three-bedroom, two-bath layout centers around a striking kitchen featuring Macassar Ebony cabinetry, black granite countertops, GE Monogram stainless steel appliances, and a sleek floating island--ideal for both everyday living and entertaining. Concrete floors complement the home's clean, modern aesthetic, while tiled and multi-level living spaces add depth and interest throughout.Step outside to a beautifully curated landscape with crushed granite, Chicago brick, and coral pathways winding through mature palms, fruit trees, and verdant plantings. The fully fenced grounds offer exceptional privacy, enhanced by a gated drive with off-street parking for two vehicles. An outdoor bar and multiple entertaining areas make this property perfect for hosting, with ample space to add a generous pool if desired.Additional features include a newly installed central air system, accordion hurricane shutters, abundant storage, and a versatile third bedroom ideal for a nursery, office, studio, or home gym. Located just a short bike ride from Old Town, this well loved home is a rare opportunity to own a true tropical retreat in one of Key West's most desirable Midtown locations.

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Property Features

  • Facts
  • Lot Size: 0.17 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 2

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 1195000
  • unparsedaddress: 2309 Flagler Avenue
  • postalcity: Key West
  • stateorprovince: FL
  • country: US
  • postalcode: 33040
  • bathroomsfull: 2
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.17
  • lotsizeunits: Acres
  • lotsizearea: 0.17
  • livingarea: 1720
  • livingareaunits: Square Feet
  • latitude: 24.557875
  • longitude: -81.776099
  • listagentfullname: Jennifer M Newman
  • listagentemail: jennifer@jennifernewman.org
  • listagentkey: 3yd-KWARFL-20131105111345781579000000
  • listagentmlsid: 20131105111345781579000000
  • listagentpreferredphone: 3236005678
  • listagentofficephone: 3052922244
  • listofficekey: 3yd-KWARFL-20070803221359772367000000
  • listagentstatelicense: 3283327
  • 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: 1953
  • listagenturl: http://www.trumanandcompany.com
  • countyorparish: Monroe
  • parcelnumber: 00045560-000000
  • appliances: Dishwasher, Dryer, Freezer, Garbage Disposer, Microwave, Refrigerator, Washer
  • numberofunitstotal: 0
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • view: Water
  • waterfrontyn: False
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bedroom 1, Bedroom 2, Bedroom 3
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.7761, 24.557875
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Truman & Co. Real Estate Services", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"jennifer@jennifernewman.org", "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/2309-Flagler-Ave_Key-West_FL_33040_M56437-00562?f=listhub&s=KWARFL&m=619530&c=rexren", "MLSModificationTimestamp":"2026-04-16T17:10:06Z", "Neighborhoods":[{"Description":null, "Name":"03 - Key West"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":6806.41, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 4/17/2026 12:05:22 AM GMT
Source Updated Date: 4/17/2026 12:44:36 PM GMT

Courtesy of: Jennifer M Newman, Truman & Co. (KW), jennifer@jennifernewman.org

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.