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81486 Overseas Highway
Upper Matecumbe Key Islamorada FL 33036 US

$22,500,000

Active Listing ID 618525
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7 bed
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9.00 Bath (7 Full , 2 Half)
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Lot: 5.82 Acres
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Single Family Residence

$22,500,000

Active Listing ID 618525
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81486 Overseas Highway Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8, 800 square feet of air conditioned living space is thoughtfully designed with bright open interiors which blend sophistication and comfort while framing breathtaking views of Florida Bay. You enter a sunlit two-story foyer leading you upstairs to a bespoke great room, encapsulating a dramatic vaulted wood ceiling, spacious living area, and a custom gourmet chef's kitchen. Floor to ceiling glass doors frame an unobstructed view of the spacious bay-view terrace, which features a 50 foot elevated infinity edge swimming pool and outdoor kitchen with bar. On the upstairs level you will also find a serene primary suite, five generous en-suite guest bedrooms, a powder room, and a large laundry room. The lower level offers a separate one bed en-suite with its own entrance and patio. A media room with adjoining bathroom is the ideal flex space. A 1, 600 square foot three car garage and a carport area completes the lower level. All told, there is nearly 25, 000 square feet under roof cover. The estate's tropical grounds are designed to complement the home's architecture. A private floating dock offers unimpeded views of Florida Bay. Located in the heart of Islamorada, this property offers rare walkability to some of the village's most recognizable attractions. This location allows you unparalleled access to the best of Islamorada's dining, entertainment, and waterfront lifestyle. Isla House represents a rare opportunity to own one of Islamorada's most unrivaled, captivating, and serene waterfront estates--a sanctuary of elegance, craftsmanship, and timeless island charm.

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Property Features

  • Facts
  • Lot Size: 5.82 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 7
  • 1/2 Bathrooms: 2
  • Exterior Finish: Rain Gutters, Storage, Outdoor Kitchen
  • Floor Covering: Tile
  • Roof Type: Metal
  • Additional Features
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 22500000
  • unparsedaddress: 81486 Overseas Highway
  • postalcity: Upper Matecumbe Key Islamorada
  • stateorprovince: FL
  • country: US
  • postalcode: 33036
  • bathroomsfull: 7
  • bathroomshalf: 2
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 5.82
  • lotsizeunits: Acres
  • lotsizearea: 5.82
  • livingarea: 8878
  • livingareaunits: Square Feet
  • latitude: 24.913707
  • longitude: -80.641702
  • listagentfullname: KELLY K SHAW PA
  • listagentemail: Kelly@kellykshaw.com
  • listagentkey: 3yd-FLKEYSMLSFL-20060624040519099643000000
  • listagentmlsid: 20060624040519099643000000
  • listagentpreferredphone: 3056647303
  • listagentofficephone: 3056644966
  • listofficekey: 3yd-FLKEYSMLSFL-20060624040345088531000000
  • listagentstatelicense: 0583328
  • listofficemlsid: 20060624040345088531000000
  • 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: 2026
  • listagenturl: http://www.KellyKShaw.com
  • countyorparish: Monroe
  • parcelnumber: 00404590000000
  • appliances: None
  • constructionmaterials: Concrete
  • flooring: Tile
  • numberofunitstotal: 1
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • parkingfeatures: Carport, Covered, Garage, Guest, RV
  • roof: Metal
  • waterfrontyn: True
  • interiorfeatures: Elevator, Walk-in Closet(s), Storage
  • exteriorfeatures: Rain Gutters, Storage, Outdoor Kitchen
  • waterfrontfeatures: 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: Outdoor Kitchen, Storage
  • accessibilityfeatures: Accessible Elevator Installed
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -80.6417, 24.913708
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"American Caribbean Real Estate", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"Kelly@kellykshaw.com", "ListBrokerageCity":"Islamorada", "ListBrokerageCountry":"US", "ListBrokerageEmail":"joy@joycmartin.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/FLKEYSMLSFL/3c6f6e61847511df917b00219b9aa4d8/20150605180948423.png", "ListBrokerageName":"American Caribbean Real Estate", "ListBrokeragePhone":"(305) 664-4966", "ListBrokeragePostalCode":"33036", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":"PO Box 353", "ListBrokerageUnparsedAddress":"81800 Overseas Highway", "ListBrokerageWebsiteUrl":"http://www.AmericanCaribbean.com", "ListOfficeAddress1":"81800 Overseas Highway", "ListOfficeAddress2":"PO Box 353", "ListOfficeBrokerMlsId":"20060624040512114550000000", "ListOfficeCity":"Islamorada", "ListOfficeCountry":"US", "ListOfficeEmail":"sales@americancaribbean.com", "ListOfficePostalCode":"33036", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential - Single Family - Upper Matecumbe Key Islamorada, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/81486-Overseas-Hwy_Islamorada_FL_33036_M68930-28839?f=listhub&s=FLKEYSMLSFL&m=618525&c=rexren", "MLSModificationTimestamp":"2026-03-06T12:34:16Z", "Neighborhoods":[{"Description":null, "Name":"23 - Upper Matecumbe"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":13278.66, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 3/6/2026 8:00:44 PM GMT
Source Updated Date: 3/27/2026 7:03:21 PM GMT

Courtesy of: KELLY K SHAW PA, American Caribbean Real Estate, Christie's International Real Estate, Kelly@kellykshaw.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.