Basic Information

  • Type Single Family Home
  • Status Active
  • Subdivision/Complex Cutthroat Harbor Est 23.0
  • Year Built 1982
  • Total Sqft 13,979
  • Date Listed 01/09/2026
  • Days on Market 5
Description

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, youre close to marinas, boating, dining, and just a short drive to the vibrant energy of Key West.Property Highlights:Oceanfront with stunning open-water viewsFully renovated interior with Keys coastal finishes Rare double lot for privacy and expansion potential4 spacious bedrooms 3 updated bathroomsExpansive outdoor living sunrisesunset viewing decksQuiet, 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!

Exterior Features

  • Waterfront No
  • Parking Spaces 0
  • Pool No
  • WF Description Ocean
  • Parking Description
  • Exterior Features Privacy WallFence

Interior Features

  • Adjusted Sqft 2,440Sq.Ft
  • Cooling Description Central Air,Ceiling Fanss
  • Floor Description Tile
  • Interior Features Cathedral Ceilings, Walk-in Closets, Granite Counter Top, Entrance Foyer
  • Sqft 2,440 Sq.Ft

Property Features

  • Aprox. Lot Size 13,979
  • Association Fee Frequency None
  • City Cudjoe Key
  • County Monroe
  • Furnished Info No
  • Patio And Porch Features Privacy WallFence
  • Sewer Description Yes
  • Short Sale Regular Sale
  • HOA Fees N/A
  • Subdivision Complex 22542 Jolly Roger
  • Subdivision Info Cutthroat Harbor Est 23.0
  • Tax Amount $12,646
  • Tax Year 2025
  • Type of Property Residential - Single Family
  • Zoning IS - Improved Subivision District

22542 Jolly Roger Dr

Cudjoe Key, FL 33042

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