Welcome to coastal living in one of the most desirable

swipe instructions
Tap to see more photos

Home For Sale

22542 Jolly Roger Drive

Cudjoe Key, Florida 33042

Monroe County

Beachfront: Yes

Ocean View: Yes

Community: Cutthroat Harbor Est (23)

map
$2,299,000 4 br, 3.0 bath 2440 sq. ft. 0.320 acres

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!

Interior:
  • Bedrooms: 4
  • Baths: 3.0
  • Sq Ft: 2440
  • Year Built: 1982
  • Utilities: 
  • Fireplaces: 
  • Stories: 
  • Heat/AC: 
  • Garage: Covered, Open, RV
Exterior:
  • Lot Size: 0.320 acre
  • Lot Dimensions: 
  • Beachfront: Yes
  • View Types: Ocean
  • Yard: 
  • Siding: Frame
  • Roof: Metal
  • Property Taxes: $12,646
  • MLS #: 618018
Get More Info
static map
Contact Information:
Beach Home For Sale in Cudjoe Key, Florida
Listing Agent: Emily Lombard, Ocean Sotheby's International Realty, 305-433-1900, 305-294-1117 Listing Site, Listing Status: Active
Copyright © 2025 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.
Ad Number: 7110317
Viewed 59 times.
Updated: Jan 09, 2026

This property is a Home located at 22542 Jolly Roger Drive, Cudjoe Key, Florida 33042, and is currently For Sale at $2,299,000. This Home has 4 bedrooms, 3.0 baths, 2440 sq ft.