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219 Preston Street
Upper Matecumbe Key Islamorada FL 33036 US

$895,000

Active Listing ID 617660
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4 bed
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2.00 Bath (2 Full)
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Lot: 0.19 Acres
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Multi Family

$895,000

Active Listing ID 617660
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219 Preston Street Back on market with Huge Price Improvement! Rare Downtown Islamorada Opportunity... Just steps to the ocean, sunrises and sunsets. Walk to everything you love in Islamorada! Located just off the Old Hwy, oceanside, in the sought-after Matecumbe Beach neighborhood on Upper Matecumbe Key. This versatile property features two charming cottages on one property, just steps from festivals, the Arts District, Library Beach, Cheeca Lodge, Historical Hurricane Monument and some of the island's finest dining. The front cottage offers 2 bedrooms and 1 bath with +/-866 sq. ft., while the back cottage includes 2 bedrooms and 1 bath with +/-900 sq. ft. Enjoy the option to live in one and rent the other, or maximize income by renting both. An exceptional investment in a prime location, right in the heart of Islamorada's most vibrant and walkable district.Important Note: This property is also listed separately in the MLS under 2 different classifications intentionally: Single Family Home and Duplex/multifamily as it can be used for both.

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Property Features

  • Facts
  • Lot Size: 0.19 Acres
  • Property Type: Residential Multi Family
  • Property Sub-type: Multi Family
  • Features
  • Full Bathrooms: 2
  • Cooling System: Ceiling Fan(s)

Property

  • propertytype: Residential Multi Family
  • propertysubtype: Multi Family
  • listprice: 895000
  • unparsedaddress: 219 Preston Street
  • postalcity: Upper Matecumbe Key Islamorada
  • stateorprovince: FL
  • country: US
  • postalcode: 33036
  • bathroomsfull: 2
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.19
  • lotsizeunits: Acres
  • lotsizearea: 0.19
  • livingarea: 1766
  • livingareaunits: Square Feet
  • latitude: 24.915581
  • longitude: -80.63573
  • listagentfullname: Patti Stanley
  • listagentemail: Patti.Stanley@me.com
  • listagentkey: 3yd-FLKEYSMLSFL-20060624040502629399000000
  • listagentmlsid: 20060624040502629399000000
  • listagentpreferredphone: 3053934433
  • listagentofficephone: 3056644470
  • listofficekey: 3yd-FLKEYSMLSFL-20060624040347191526000000
  • listagentstatelicense: 0427521
  • listofficemlsid: 20060624040347191526000000
  • 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: 1934
  • listagenturl: http://www.floridakeysnativeconnection.com/
  • countyorparish: Monroe
  • parcelnumber: 00401940-000000
  • appliances: Range, Refrigerator
  • cooling: Ceiling Fan(s)
  • constructionmaterials: Frame, Stucco
  • numberofunitstotal: 0
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • view: Water
  • waterfrontyn: False
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -80.63573, 24.91558
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Coldwell Banker Schmitt Islamorada", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"Patti.Stanley@me.com", "ListBrokerageCity":"ISLAMORADA", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Coldwell Banker Schmitt Islamorada", "ListBrokeragePhone":"(305) 664-4470", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"85996 Overseas Highway", "ListBrokerageWebsiteUrl":"http://www.realestatefloridakeys.com", "ListOfficeAddress1":"85990 Overseas Highway", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"20060624040415714463000000", "ListOfficeCity":"ISLAMORADA", "ListOfficeCountry":"US", "ListOfficeEmail":"marysanchez14@yahoo.com", "ListOfficePostalCode":"33036", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Multi-family - Upper Matecumbe Key Islamorada, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/219-Preston-St_Islamorada_FL_33036_M56104-66217?f=listhub&s=FLKEYSMLSFL&m=617660&c=rexren", "MLSModificationTimestamp":"2026-02-27T11:46:51Z", "Neighborhoods":[{"Description":null, "Name":"23 - Upper Matecumbe"}], "PostalCode":null, "RawPropertySubType":"Multi-family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":7749.71, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 2/27/2026 8:00:45 PM GMT
Source Updated Date: 2/28/2026 12:46:59 PM GMT

Courtesy of: Patti Stanley, Coldwell Banker Schmitt Islamorada, Patti.Stanley@me.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.