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89505 Old Highway
Plantation Key FL 33070 US

$26,400,000

Active Listing ID 620022
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7 bed
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8.00 Bath (6 Full , 4 Half)
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Lot: 7.64 Acres
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Single Family Residence

$26,400,000

Active Listing ID 620022
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89505 Old Highway Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind gates on Plantation Key, this secluded retreat combines lush tropical landscaping with unmatched privacy for the ultimate island escape. The 8, 988-square-foot main residence showcases exceptional craftsmanship and thoughtful design. One wing features a dramatic two-story primary suite with a private office, while the opposite wing includes four additional bedrooms and four bathrooms across two levels. A separate two-bedroom guest house provides extra space for visitors, and a whole-house generator adds convenience and peace of mind. Inside, custom woodwork, coffered ceilings, built-ins, and high-end finishes create a warm yet refined atmosphere. Amenities include a chef's kitchen, wine cellar, private gym, elevator, and seamless indoor-outdoor living spaces ideal for entertaining or relaxing by the water. Resort-style outdoor features include a custom pool, tiki bar, outdoor kitchen, beachside fire pit, putting green, observation pier, and a lighted tennis court with cabana. Convenient access by seaplane, helicopter, or a 90-minute drive from Miami makes travel effortless. Perfect for boating enthusiasts, the estate is near dockage and concierge dry storage options. Located in the heart of Islamorada, Palm Paradise offers easy access to world-class fishing, boating, dining, and the laid-back luxury of the Florida Keys. Offered at $26.4M, Palm Paradise is a rare opportunity to own a private waterfront compound ideal for luxury living, family retreats, or executive escapes.

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Property Features

  • Facts
  • Lot Size: 7.64 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 6
  • 1/2 Bathrooms: 4
  • Cooling System: Ductless, Central Air
  • Exterior Finish: Bar, Built-in Grill, Chickee Hut, Fencing, Gazebo, Detached Guest Qtrs, Hot Tub, Lighting, Lanai, Outdoor Kitchen, Outdoor Shower, Privacy Wall/Fence, Sandy Beach, Sprinkler System, Storage, Tennis Court(s), Water Display
  • Floor Covering: Tile, Wood, Marble
  • Roof Type: Metal
  • Heating Fuels: Central
  • Additional Features
  • Patio
  • Pool
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 26400000
  • unparsedaddress: 89505 Old Highway
  • postalcity: Plantation Key
  • stateorprovince: FL
  • country: US
  • postalcode: 33070
  • bathroomsfull: 6
  • bathroomshalf: 4
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 7.64
  • lotsizeunits: Acres
  • lotsizearea: 7.64
  • livingarea: 8988
  • livingareaunits: Square Feet
  • latitude: 24.989133
  • longitude: -80.53931
  • listagentfullname: Leslie Leopold
  • listagentemail: LLeopold@Oceansir.com
  • listagentkey: 3yd-FLKEYSMLSFL-20060624040453046599000000
  • listagentmlsid: 3071091
  • listagentpreferredphone: 3059420215
  • listagentofficephone: 3059420215
  • listofficekey: 3yd-FLKEYSMLSFL-20100727151734715717000000
  • listagentstatelicense: 3071091
  • listofficemlsid: 2022737
  • 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: 2008
  • listingcontractdate: 2026-05-24
  • listagenturl: liveislamorada.com
  • countyorparish: Monroe
  • parcelnumber: 00092570000100
  • appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Gas Appliances, Ice Machine, Wine Cooler, Stainless Steel Appliance(s)
  • cooling: Ductless, Central Air
  • constructionmaterials: CBS, Concrete
  • flooring: Tile, Wood, Marble
  • heating: Central
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Open
  • roof: Metal
  • view: Ocean, Water
  • waterfrontyn: True
  • franchiseaffiliation: None
  • interiorfeatures: Built-in Cabinets, Granite Counter Top, Elevator, Security System, Storage, Walk-in Closet(s), Bar, Gym, Loft, Sauna, Sun/Florida Room
  • exteriorfeatures: Bar, Built-in Grill, Chickee Hut, Fencing, Gazebo, Detached Guest Qtrs, Hot Tub, Lighting, Lanai, Outdoor Kitchen, Outdoor Shower, Privacy Wall/Fence, Sandy Beach, Sprinkler System, Storage, Tennis Court(s), Water Display
  • waterfrontfeatures: Ocean Front
  • rooms: Bedroom 6, Bathroom 3, Bedroom 7, Bathroom 4, Bathroom 2, Bathroom 9, Bathroom 7, Bedroom 3, Bathroom 1, Bedroom 5, Bedroom 1, Bathroom 8, Bathroom 10, Exercise Room, Bathroom 6, Bedroom 2, Bathroom 5, Bedroom 4
  • securityfeatures: Security System
  • otherstructures: Gazebo, Storage, Outdoor Kitchen
  • utilities: Cable Available
  • patioandporchfeatures: Patio, Porch, Deck
  • accessibilityfeatures: Accessible Elevator Installed
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Fenced, Privacy
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -80.53931, 24.989134
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Ocean Sotheby's International Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"LLeopold@Oceansir.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":"20100727151734715717000000", "ListOfficeCity":"Islamorada", "ListOfficeCountry":"US", "ListOfficeEmail":"russell.post@sothebysrealty.com", "ListOfficePostalCode":"33036", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Plantation Key, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/89505-Old-Hwy_Tavernier_FL_33070_M58986-74140?f=listhub&s=FLKEYSMLSFL&m=620022&c=rexren", "MLSModificationTimestamp":"2026-05-24 14:14:14", "Neighborhoods":[{"Description":null, "Name":"Trop Coral Reef (89.0)"}], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":58331, "TaxDescription":"5 63 38 Plantation Key Or Long Island Pt Govt Lot 6 & Adj Bay Btm Se'ly G37-221 Or186-271(Ii Deed 22485) Or556-986/89 Or", "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 5/25/2026 3:16:37 AM GMT
Source Updated Date: 5/26/2026 6:40:34 PM GMT

Courtesy of: Leslie Leopold, Ocean Sotheby's International Realty, LLeopold@Oceansir.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.