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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.
Featured Listing
417 Pirates Road, Little Torch Key (Jolly Roger Estates) - courtesy of Maggie Beall, LoKation Real Estate
Full photos, details, and current price are at the link below.
View 417 Pirates Road listing details
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
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
MOTIVATED SELLER! Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in r...
- 3 Beds
- 2 Baths
- 620124 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
Stunning furnished 3-bedroom, 2-bath waterfront retreat in the sought-after Jolly Rogers subdivision, featuring a deep flow-through canal with no bridges to open water, p...
- 3 Beds
- 2 Baths
- 619662 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
Discover waterfront living in Jolly Roger Estates on Little Torch Key. This beautifully maintained 3 bedroom, 3 bathroom canal-front home offers quick boating access to o...
- 3 Beds
- 3 Baths
- 619055 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
This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishin...
- 3 Beds
- 3 Baths
- 614486 MLS
Welcome to this beautifully updated canal-front home in the highly desirable Jolly Roger Estates on Little Torch Key! Offering 3 bedrooms, 2 baths, 1,170 sq ft of living ...
- 3 Beds
- 2 Baths
- 618340 MLS
Located near a canal 'T', this oceanside property offers easy docking for larger boats and sailboats in the 50 ft. wide, flow-through canal, putting the Atlantic and back...
- 2 Beds
- 2 Baths
- 618566 MLS
Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this prop...
- 3 Beds
- 2 Baths
- 617991 MLS
