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82719 Old Highway
Upper Matecumbe Key Islamorada FL 33036 US

$24,995,000

Active Listing ID 619281
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7 bed
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11.00 Bath (10 Full , 1 Half)
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Lot: 1.83 Acres
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Single Family Residence

$24,995,000

Active Listing ID 619281
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82719 Old Highway Experience unparalleled oceanfront living at the Chateau on the Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly unforgettable. Completely reimagined and newly constructed in 2023, this residence showcases exceptional modern design, engineering, and craftsmanship. Set on just under 2 acres of pristine coastline, the property offers 19, 784 SF of total living and entertaining space, including 10, 182 SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors with natural light and highlighting refined, couture-level finishes. Amenities include a fitness center, indoor basketball and pickleball court, a Baccarat-inspired grand ballroom, and a custom Glamour Suite. Outdoors, a mosaic pool and spa overlook the Atlantic Ocean, complemented by alfresco dining, a firepit lounge, and multiple terraces with sweeping coastal views. A 300 inch outdoor LED theater and rooftop terrace elevate the experience. A 100ft private dock provides direct ocean access. Approved plans include 6 additional suites, including 2 oceanfront residences, allowing expansion into a multi-structure compound. A rare legacy estate defined by privacy, scale, and presence

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Property Features

  • Facts
  • Lot Size: 1.83 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 10
  • 1/2 Bathrooms: 1
  • Exterior Finish: Bar, Water Display, Storage, Shed, Sandy Beach, Privacy Wall/Fence, Outdoor Shower, Outdoor Kitchen, Lighting, Hot Tub, Rain Gutters, Built-in Grill
  • Floor Covering: Concrete, Marble, Wood
  • Roof Type: Concrete
  • Additional Features
  • Fireplace
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 24995000
  • unparsedaddress: 82719 Old Highway
  • postalcity: Upper Matecumbe Key Islamorada
  • stateorprovince: FL
  • country: US
  • postalcode: 33036
  • bathroomsfull: 10
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 1.83
  • lotsizeunits: Acres
  • lotsizearea: 1.83
  • livingarea: 10182
  • livingareaunits: Square Feet
  • latitude: 24.92643
  • longitude: -80.623116
  • listagentfullname: Pamela DiMartino
  • listagentemail: pamdimar@aol.com
  • listagentkey: 3yd-FLKEYSMLSFL-20260402121550546460000000
  • listagentmlsid: 20260402121550546460000000
  • listagentpreferredphone: 3058077089
  • listagentofficephone: 3059318266
  • listofficekey: 3yd-FLKEYSMLSFL-20220617193416974778000000
  • listagentstatelicense: 3123363
  • listofficemlsid: 20220617193416974778000000
  • 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: 1995
  • listagenturl: http://www.pamdimartino.com
  • countyorparish: Monroe
  • parcelnumber: 00401300000000
  • appliances: Dishwasher, Dryer, Freezer, Garbage Disposer, Microwave, Range, Refrigerator, Washer
  • constructionmaterials: Concrete
  • flooring: Concrete, Marble, Wood
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 3
  • parkingtotal: 0
  • parkingfeatures: Carport, Garage
  • roof: Concrete
  • view: Ocean, Water
  • waterfrontyn: True
  • interiorfeatures: Drapes/Blinds Incl, Built-in Cabinets, Bar, Window Treatments, Whirlpool Bath Tub, Walk-in Closet(s), Storage, Smoke Alarms, Security System, Fire Sprinkler, Elevator, Granite Counter Top, Entrance Foyer, Pantry, Intercom, Fireplace(s), Split Bedroom, Cathedral Ceilings, Wet Bar
  • exteriorfeatures: Bar, Water Display, Storage, Shed, Sandy Beach, Privacy Wall/Fence, Outdoor Shower, Outdoor Kitchen, Lighting, Hot Tub, Rain Gutters, Built-in Grill
  • 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
  • securityfeatures: Security System
  • otherstructures: Outdoor Kitchen, Packing Shed, Shed(s), Storage
  • accessibilityfeatures: Accessible Elevator Installed
  • dock: False
  • poolprivateyn: False
  • spayn: True
  • fencing: Fenced, Privacy
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -80.623116, 24.92643
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Coldwell Banker Realty - Adventura", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"pamdimar@aol.com", "ListBrokerageCity":"Aventura", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Coldwell Banker Realty - Adventura", "ListBrokeragePhone":"(305) 931-8266", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":"#102", "ListBrokerageUnparsedAddress":"20803 Biscayne Blvd", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"20803 Biscayne Blvd", "ListOfficeAddress2":"#102", "ListOfficeBrokerMlsId":"20220617193757731051000000", "ListOfficeCity":"Aventura", "ListOfficeCountry":"US", "ListOfficeEmail":"donna.reid@floridamoves.com", "ListOfficePostalCode":"33180", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential - Single Family - Upper Matecumbe Key Islamorada, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/82719-Old-Hwy_Islamorada_FL_33036_M65850-75535?f=listhub&s=FLKEYSMLSFL&m=619281&c=rexren", "MLSModificationTimestamp":"2026-04-16T08:18:02Z", "Neighborhoods":[{"Description":null, "Name":"23 - Upper Matecumbe"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":54965.67, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 4/16/2026 4:00:44 PM GMT
Source Updated Date: 4/17/2026 6:44:12 PM GMT

Courtesy of: Pamela DiMartino, Coldwell Banker Realty - Aventura, pamdimar@aol.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.