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22542 Jolly Roger Drive
Cudjoe Key FL 33042 US

$2,299,000

Active Listing ID 618018
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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

$2,299,000

Active Listing ID 618018
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22542 Jolly Roger Drive Welcome to coastal living in one of the most desirable neighborhoods in Cudjoe Key. This beautifully renovated 4-bedroom, 3-bath oceanfront residence sits proudly on a rare double lot, offering unmatched space, privacy, and breathtaking open-water views. Step inside to discover a bright, airy living space with stylish coastal finishes, vaulted ceilings, and walls of windows that frame the sparkling turquoise sea. The newly upgraded kitchen features high-end appliances, custom cabinetry, and a spacious island perfect for gathering with family and friends. Enjoy seamless indoor-outdoor living with expansive decks overlooking the water--perfect for sunrise coffee, sunset cocktails, or dining al fresco. The oversized property provides plenty of room to unwind, entertain, or dream up future additions like a pool, tiki or guest cottage. With four generous bedrooms--including a serene oceanfront primary suite--everyone has room to relax and recharge. The home is move-in ready with modern updates throughout, including new flooring, fixtures, and fresh coastal-inspired decor. Located in a quiet, sought-after Cudjoe Key neighborhood, you're close to marinas, boating, dining, and just a short drive to the vibrant energy of Key West.Property Highlights:*Oceanfront with stunning open-water views*Fully renovated interior with Keys coastal finishes *Rare double lot for privacy and expansion potential*4 spacious bedrooms / 3 updated bathrooms*Expansive outdoor living & sunrise/sunset viewing decks*Quiet, upscale neighborhood with easy access to boating and Key West.This is Keys living at its absolute finest--your dream home by the sea awaits!

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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
  • Cooling System: Ceiling Fan(s)
  • Exterior Finish: Privacy Wall/Fence
  • Floor Covering: Tile
  • Roof Type: Metal
  • Additional Features
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 2299000
  • 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: Emily Lombard
  • listagentemail: elombard@oceansir.com
  • listagentkey: 3yd-KWARFL-20170512180230503842000000
  • listagentmlsid: 20170512180230503842000000
  • listagentpreferredphone: 3054331900
  • listagentofficephone: 3052941117
  • listofficekey: 3yd-KWARFL-20171117190843578060000000
  • listagentstatelicense: 3383417
  • listofficemlsid: 20171117190843578060000000
  • 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
  • listagenturl: http://www.oceansir.com
  • countyorparish: Monroe
  • parcelnumber: 00180480-000000
  • appliances: Dishwasher, Dryer, Refrigerator, Washer
  • cooling: Ceiling Fan(s)
  • constructionmaterials: Frame
  • flooring: Tile
  • numberofunitstotal: 0
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Covered, Open, RV
  • roof: Metal
  • view: Ocean
  • waterfrontyn: True
  • interiorfeatures: Cathedral Ceilings, Walk-in Closet(s), Granite Counter Top, Entrance Foyer
  • exteriorfeatures: Privacy Wall/Fence
  • 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
  • fencing: Fenced, Privacy
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.48283, 24.661388
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Ocean Sotheby's International Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"elombard@oceansir.com", "ListBrokerageCity":"Key West", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Ocean Sotheby's International Realty", "ListBrokeragePhone":"(305) 294-1117", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"420 Fleming St", "ListBrokerageWebsiteUrl":"http://www.oceansir.com", "ListOfficeAddress1":"1075 Duval Street, 15C", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"20171117204305469866000000", "ListOfficeCity":"Key West", "ListOfficeCountry":"US", "ListOfficeEmail":"russell@oceanreefclubsir.com", "ListOfficePostalCode":"33040", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential - 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=618018&c=rexren", "MLSModificationTimestamp":"2026-01-09T13:57:10Z", "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: 1/9/2026 10:05:26 PM GMT
Source Updated Date: 1/12/2026 6:48:09 PM GMT

Courtesy of: Emily Lombard, Ocean Sotheby's International Realty, elombard@oceansir.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.