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83407 Old Highway
Upper Matecumbe Key Islamorada FL 33036 US

$6,750,000

Active Listing ID 619150
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6 bed
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5.00 Bath (5 Full)
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Lot: 0.57 Acres
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Single Family Residence

$6,750,000

Active Listing ID 619150
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83407 Old Highway This breathtaking three-story beachfront estate offers the ultimate blend of resort-style living and refined comfort. Featuring six spacious bedrooms and five luxurious bathrooms, and three inviting living rooms, home is designed to accommodate both relaxation and entertainment with ease. Set in a serene cove with a pristine natural beach, the home showcases floor-to-ceiling windows that frame sweeping180-degree views. Every space is thoughtfully curated with elegant, coastal-inspired decor, creating an atmosphere that feels both sophisticated and personal. Located in downtown Islamorada in the Florida Keys, the property includes a private beach, a tranquil oceanfront pool, and a charming tiki hut perfect for shaded lounging. Outdoor living is elevated by a cozy firepit, offering an intimate setting for gatherings. As a vacation rental, this home presents a high-yield investment opportunity in a highly sought-after area. This home is a true masterpiece, offering unparalleled luxury, privacy, and breathtaking views.

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Property Features

  • Facts
  • Lot Size: 0.57 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 5
  • Cooling System: Ceiling Fan(s)
  • Exterior Finish: Chickee Hut, Storage, Sandy Beach, Privacy Wall/Fence, Fencing
  • Floor Covering: Tile
  • Roof Type: Metal
  • Additional Features
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 6750000
  • unparsedaddress: 83407 Old Highway
  • postalcity: Upper Matecumbe Key Islamorada
  • stateorprovince: FL
  • country: US
  • postalcode: 33036
  • bathroomsfull: 5
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.57
  • lotsizeunits: Acres
  • lotsizearea: 0.57
  • livingarea: 4566
  • livingareaunits: Square Feet
  • latitude: 24.935158
  • longitude: -80.614289
  • listagentfullname: Cheri Tindall
  • listagentemail: cheri@floridakeysbestbuys.com
  • listagentkey: 3yd-FLKEYSMLSFL-20060624040501175719000000
  • listagentmlsid: 20060624040501175719000000
  • listagentpreferredphone: 3056647661
  • listagentofficephone: 3057128888
  • listofficekey: 3yd-FLKEYSMLSFL-20100727151734715717000000
  • listagentstatelicense: 0411868
  • listofficemlsid: 20100727151734715717000000
  • disclaimer: Copyright © 2026 Florida Keys Board 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: FLKEYSMLSFL
  • yearbuilt: 1992
  • listagenturl: http://www.floridakeysbestbuys.com
  • countyorparish: Monroe
  • parcelnumber: 00404020000000
  • appliances: Dishwasher, Dryer, Garbage Disposer, Microwave, Range, Refrigerator, Washer
  • cooling: Ceiling Fan(s)
  • flooring: Tile
  • numberofunitstotal: 0
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 3
  • parkingtotal: 0
  • parkingfeatures: Open
  • roof: Metal
  • view: Ocean
  • waterfrontyn: True
  • interiorfeatures: Drapes/Blinds Incl, Quartz Countertops, Window Treatments, Storage, Entrance Foyer
  • exteriorfeatures: Chickee Hut, Storage, Sandy Beach, Privacy Wall/Fence, Fencing
  • waterfrontfeatures: Oceanfront, Waterfront
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5
  • otherstructures: Storage
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • fencing: Fenced, Privacy
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -80.61429, 24.935158
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Ocean Sotheby's International Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"cheri@floridakeysbestbuys.com", "ListBrokerageCity":"Islamorada", "ListBrokerageCountry":"US", "ListBrokerageEmail":"russell.post@sothebysrealty.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Ocean Sotheby's International Realty", "ListBrokeragePhone":"3057128888", "ListBrokeragePostalCode":"33036", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"81888 Overseas Hwy", "ListBrokerageWebsiteUrl":"http://www.oceansir.com", "ListOfficeAddress1":"81888 Overseas Hwy", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"20200515211417486585000000", "ListOfficeCity":"Islamorada", "ListOfficeCountry":"US", "ListOfficeEmail":"russell.post@sothebysrealty.com", "ListOfficePostalCode":"33036", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential - Single Family - Upper Matecumbe Key Islamorada, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/83407-Old-Hwy_Islamorada_FL_33036_M50823-90020?f=listhub&s=FLKEYSMLSFL&m=619150&c=rexren", "MLSModificationTimestamp":"2026-03-21T07:25:32Z", "Neighborhoods":[{"Description":null, "Name":"23 - Upper Matecumbe"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":31796.02, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 3/21/2026 2:00:45 PM GMT
Source Updated Date: 3/26/2026 7:28:29 AM GMT

Courtesy of: Cheri Tindall, Ocean Sotheby's International Realty, cheri@floridakeysbestbuys.com

Copyright © 2026 Florida Keys Board 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.