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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 This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces to showcase a breathtaking oceanfront setting. 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 along the shoreline.Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living, while large impact glass doors and windows frame sweeping ocean views and invite natural light into every room. Soaring ceilings enhance the open-concept layout with dark wood beams amplifying the impact. The main floor living space includes a fully renovated kitchen, dining space, capacious living room, laundry, two bedrooms and two bathrooms. Ascend to the top 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 the home's optimal panoramic views.The home itself tells a story through design; masterfully blending opposites in a way to complement each other: masculine and feminine, modern lines and traditional warmth, cozy intimacy within spacious rooms. The thoughtful juxtaposition and melding of these elements transform the residence into a statement of artistic expression. Whimsical, eclectic touches are paired with bold architectural features, creating visual intrigue throughout.

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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
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-FLKEYSMLSFL-618818", "OpenHouseEndTime": "2026-02-28T18:00:00+00:00", "OpenHouseId": "618818", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-02-28T16:00:00+00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • 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":"2026-02-26T10:14:48Z", "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: 2/26/2026 6:00:43 PM GMT
Source Updated Date: 2/27/2026 7:07:01 AM 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.