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22542 Jolly Roger Drive
Cudjoe Key FL 33042 US

$1,725,000

Active Listing ID 619558
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4 bed
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3.00 Bath (3 Full)
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Lot: 0.15 Acres
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Single Family Residence

$1,725,000

Active Listing ID 619558
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22542 Jolly Roger Drive Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. 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: 0.15 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • Cooling System: Central Air
  • Roof Type: Metal
  • Additional Features
  • Patio
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 1725000
  • unparsedaddress: 22542 Jolly Roger Drive
  • postalcity: Cudjoe Key
  • stateorprovince: FL
  • country: US
  • postalcode: 33042
  • bathroomsfull: 3
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.15
  • lotsizeunits: Acres
  • lotsizearea: 0.15
  • livingarea: 2440
  • livingareaunits: Square Feet
  • latitude: 24.661387
  • longitude: -81.482829
  • listagentfullname: Lauren Hoefert Dunn
  • listagentemail: hoefertdunnrealestate@gmail.com
  • listagentkey: 3yd-KWARFL-20210625201915736062000000
  • listagentmlsid: 3505304
  • listagentpreferredphone: 3053943717
  • listofficekey: 3yd-KWARFL-20060624040347191526000000
  • listofficemlsid: 3146
  • disclaimer: Copyright © 2026 Key West Association 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: KWARFL
  • yearbuilt: 1982
  • listingcontractdate: 2026-04-13
  • listagenturl: floridakeys-houses.com
  • countyorparish: Monroe
  • parcelnumber: 00180480000000
  • appliances: Washer, Dryer, Dishwasher, Refrigerator, Oven, Wine Cooler, Stainless Steel Appliance(s)
  • cooling: Central Air
  • constructionmaterials: Frame
  • 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, Walk-in Closet(s), Quartz Countertops
  • waterfrontfeatures: Ocean Front
  • rooms: Bedroom 1, Bedroom 4, Bedroom 3, Bathroom 2, Bathroom 3, Bedroom 2, Bathroom 1
  • patioandporchfeatures: Porch, Deck
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.48283, 24.661386
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Coldwell Banker Schmitt Islamorada", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"hoefertdunnrealestate@gmail.com", "ListBrokerageCity":"Islamorada", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Coldwell Banker Schmitt Islamorada", "ListBrokeragePhone":"3056644470", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"85990 Overseas Highway ", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"85990 Overseas Highway ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"20060624040347191526000000", "ListOfficeCity":"Islamorada", "ListOfficeCountry":"US", "ListOfficeEmail":"customercare@cbschmitt.com", "ListOfficePostalCode":"33036", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Cudjoe Key, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/22542-Jolly-Roger-Dr_Cudjoe-Key_FL_33042_M61219-34402?f=listhub&s=KWARFL&m=619558&c=rexren", "MLSModificationTimestamp":"2026-05-23 18:15:48", "Neighborhoods":[{"Description":null, "Name":"Cutthroat Harbor Est (23.0)"}], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":12646, "TaxDescription":"Bk 19 Lt 36 Cutthroat Harbor Estates Cudjoe Key Pb4-165 Or222-580 Or781-1811D/C Or781-1812/14 Or781-1815 Or781-1818/19 O", "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 6/3/2026 4:37:30 AM GMT
Source Updated Date: 6/4/2026 12:54:43 AM GMT

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

Copyright © 2026 Key West Association 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.