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150 List Street
Upper Matecumbe Key Islamorada FL 33036 US

$4,900,000

Active Listing ID 618918
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1 bed
bath icon
1.00 Bath (1 Full)
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Single Family Residence

$4,900,000

Active Listing ID 618918
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150 List Street Discover an extraordinary opportunity to own 34, 000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20, 000 lb and 16, 000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to secure a premier bayfront parcel in one of Islamorada's most sought-after locations. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4, 872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This vision blends refined indoor living with outdoor elegance, creating a seamless waterfront sanctuary. Whether you envision a private coastal retreat or an entertainer's paradise, this remarkable bayfront estate offers endless possibilities in an unparalleled setting.

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Property Features

  • Facts
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 1
  • Cooling System: Ceiling Fan(s)
  • Floor Covering: Tile, Wood
  • Roof Type: Concrete
  • Additional Features
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 4900000
  • unparsedaddress: 150 List Street
  • postalcity: Upper Matecumbe Key Islamorada
  • stateorprovince: FL
  • country: US
  • postalcode: 33036
  • bathroomsfull: 1
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeunits: Acres
  • livingarea: 946
  • livingareaunits: Square Feet
  • listagentfullname: Bonnie Ekblom Oliver
  • listagentemail: bonnie.ekblom.oliver@gmail.com
  • listagentkey: 3yd-FLKEYSMLSFL-20121207194202603094000000
  • listagentmlsid: 20121207194202603094000000
  • listagentpreferredphone: 3053941569
  • listagentofficephone: 3057128888
  • listofficekey: 3yd-FLKEYSMLSFL-20100727151734715717000000
  • listagentstatelicense: 3186690
  • 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: 1950
  • listagenturl: https://oceansir.com
  • countyorparish: Monroe
  • parcelnumber: 00399820-000000
  • appliances: Dishwasher, Microwave, Range, Refrigerator, Washer
  • cooling: Ceiling Fan(s)
  • flooring: Tile, Wood
  • numberofunitstotal: 0
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Open
  • roof: Concrete
  • view: Water
  • waterfrontyn: True
  • interiorfeatures: Granite Counter Top
  • waterfrontfeatures: Waterfront
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bedroom 1
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Ocean Sotheby's International Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"bonnie.ekblom.oliver@gmail.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/150-List-St_Islamorada_FL_33036_M56418-18064?f=listhub&s=FLKEYSMLSFL&m=618918&c=rexren", "MLSModificationTimestamp":"2026-03-04T12:22:06Z", "Neighborhoods":[{"Description":null, "Name":"23 - Upper Matecumbe"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":5995.43, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 3/4/2026 8:00:44 PM GMT
Source Updated Date: 3/28/2026 6:51:25 PM GMT

Courtesy of: Bonnie Ekblom Oliver, Ocean Sotheby's International Realty, bonnie.ekblom.oliver@gmail.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.