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22542 Jolly Roger Drive
Cudjoe Key FL 33042 US

$2,100,000

Active Listing ID 618818
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4 bed
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3.00 Bath (3 Full)
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Lot: 0.32 Acres
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Single Family Residence

$2,100,000

Active Listing ID 618818
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22542 Jolly Roger Drive FULLY RESTORED! This 4-bedroom, 3-bathroom home is a testament to coastal architecture. Situated on a double lot, totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking Cudjoe Bay -- a rare and commanding presence on the shoreline.Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living. Large impact glass doors and windows frame ocean views and invite natural light into every room. Soaring, 26' ceilings enhance the open-concept layout with rich wood beams amplifying the aesthetic. The main floor living space includes a renovated and modern kitchen, dining space, living room, laundry, two bedrooms and two bathrooms. Ascend to the upper floor to find a third bedroom perched at the top of the stairs. A catwalk connects the fourth bedroom with ensuite bath and walkout deck that provides spectacular panoramic open water views.The home itself tells a story through design. Restored to its former glory, with additional modern amenities, and blending rustic accents with open, light-filled spaces to showcase the oceanfront setting. This home needs to be seen to be fully appreciated. Schedule your showing today!

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Property Features

  • Facts
  • Lot Size: 0.32 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • Roof Type: Metal
  • Additional Features
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 2100000
  • unparsedaddress: 22542 Jolly Roger Drive
  • postalcity: Cudjoe Key
  • stateorprovince: FL
  • country: US
  • postalcode: 33042
  • bathroomsfull: 3
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.32
  • lotsizeunits: Acres
  • lotsizearea: 0.32
  • livingarea: 2440
  • livingareaunits: Square Feet
  • latitude: 24.661388
  • longitude: -81.482829
  • listagentfullname: Lauren Hoefert Dunn
  • listagentemail: hoefertdunnrealestate@gmail.com
  • listagentkey: 3yd-FLKEYSMLSFL-20210625201915736062000000
  • listagentmlsid: 20210625201915736062000000
  • listagentpreferredphone: 3053943717
  • listagentofficephone: 3056644470
  • listofficekey: 3yd-FLKEYSMLSFL-20060624040347191526000000
  • listagentstatelicense: 3505304
  • 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: 1982
  • listagenturl: http://floridakeys-houses.com
  • countyorparish: Monroe
  • parcelnumber: 00180480-000000
  • appliances: Dishwasher, Dryer, Refrigerator, Washer
  • constructionmaterials: Frame
  • numberofunitstotal: 0
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Covered, Open
  • roof: Metal
  • view: Ocean, Water
  • waterfrontyn: True
  • interiorfeatures: Cathedral Ceilings, Quartz Countertops, Walk-in Closet(s), Granite Counter Top, Built-in Cabinets, Entrance Foyer
  • waterfrontfeatures: Oceanfront, Waterfront
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.48283, 24.661388
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Coldwell Banker Schmitt Islamorada", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"hoefertdunnrealestate@gmail.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":"Residential - Single Family - Cudjoe Key, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/22542-Jolly-Roger-Dr_Summerland-Key_FL_33042_M61219-34402?f=listhub&s=FLKEYSMLSFL&m=618818&c=rexren", "MLSModificationTimestamp":"2026-03-22T10:47:06Z", "Neighborhoods":[{"Description":null, "Name":"07 - Cudjoe Key"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":12645.68, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 4/7/2026 7:00:44 PM GMT
Source Updated Date: 4/13/2026 6:50:03 PM GMT

Courtesy of: Lauren Hoefert Dunn, Coldwell Banker Schmitt Islamorada, hoefertdunnrealestate@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.