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Jolly Roger Estates is located near Mile Marker 28.5 on the ocean side of Little Torch Key in the Lower Florida Keys, south of Big Pine Key. Homes here sit on flow-through canals leading to open water and under a five-minute idle zone out to the Atlantic. The neighborhood is well established and popular with serious boating, fishing, and diving households. Properties range from updated single-family homes to larger luxury builds and pre-construction projects. Big Pine Key is about 10 minutes north, Marathon roughly 25 minutes, and Key West about 35 minutes south.
Active MLS Listings are shown below. If you are particularly interested in this neighborhood, click to view the updated Market Report for Jolly Roger Estates. You will see all active listings, pending sales (if available), and home sales within the past two years.
Jolly Roger Estates
Welcome to your piece of paradise in the Florida Keys! This beautifully situated 3-bedroom, 2-bathroom canal-front home offers the perfect combination of comfort, privacy...
- 3 Beds
- 2 Baths
- 621786 MLS
Searching for your piece of Keys paradise? Here it is! This tropical gem offers island living inside and out, excellent oceanside boating, sunset views over protected wet...
- 3 Beds
- 2 Baths
- 621484 MLS
Your Florida Keys Retirement Retreat--and Investment Opportunity--Minutes from Key West Imagine waking up in the Florida Keys, stepping outside to your boat, and knowi...
- 2 Beds
- 2 Baths
- 621295 MLS
Rare actively permitted waterfront homesite with existing concrete seawall/dock on Little Torch Key with exceptional boating access, approved engineered house plans, and ...
- 620926 MLS
Canal-front vacant land with a building permit already in process -- Permit #SFDUP-2025-0096, holding 41.5 ROGO points, buy and build later. Plans are drawn for a 3,497 s...
- 620488 MLS
Canal-front with Open Water Views on a corner lot vacant land with a building permit already in process -- Permit #SFDUP-2025-0111, holding 41.5 ROGO points. Plans are dr...
- 620486 MLS
Location, location, location. This home has stunning sunrise and ocean views from this one- of-a kind Open Water property. Picture perfect views from theFrench Doors of...
- 2 Beds
- 2 Baths
- 619868 MLS
Pre-Construction Luxury Home | Jolly Roger Estates Introducing a rare pre-construction opportunity in the desirable waterfront community of Jolly Roger Estates. This...
- 5 Beds
- 4 Baths
- 619117 MLS
Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covere...
- 3 Beds
- 2 Baths
- 617537 MLS
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Homes over $3 million
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