Jolly Roger Estates (28.5) Homes for Sale

Jolly Roger Estates (28.5) Homes for Sale

Welcome to Jolly Roger Estates, a hidden gem nestled in the heart of Little Torch, Florida! This enchanting subdivision, set in the picturesque Monroe County, offers an idyllic blend of tropical charm and laid-back living that makes it a prime destination for homebuyers seeking their slice of paradise.

Jolly Roger Estates is renowned for its serene atmosphere and stunning waterfront views, making it a perfect haven for nature lovers and boating enthusiasts alike. With direct access to the crystal-clear waters of the Florida Keys, residents can enjoy a variety of water activities, from fishing and kayaking to simply soaking up the sun on your private dock. The lush landscaping and vibrant tropical flora surrounding the community create a tranquil environment that’s hard to resist.

For those looking to purchase a home, Jolly Roger Estates boasts a diverse selection of properties for sale. Whether you're in search of a cozy retreat or a spacious family home, this subdivision has something for everyone. Many homes feature modern amenities, open floor plans, and breathtaking views, ensuring that you can enjoy the best of Florida living.

In addition to the beautiful homes, the community is conveniently located near local shops, restaurants, and recreational opportunities. With its warm weather, friendly neighbors, and vibrant lifestyle, Jolly Roger Estates is not just a place to live; it’s a place to thrive. Explore the homes for sale today and discover the perfect backdrop for your new chapter in sunny Florida!

Newest Jolly Roger Estates (28.5) Homes for Sale

$1,099,999
3 Beds ⋅ 2 Baths ⋅ 621077 MLS
Escape to paradise with this incredible waterfront property located on a deep boating canal in the heart of the Lower Florida Keys. Perfectly suited for boating enthusiasts and water lovers, this home offers dockage and a boat lift, and direct, easy access to the open waters of the Atlantic Ocean and Gulf of Mexico, making it a dream come true for those who enjoy fishing, cruising, or simply relaxing by the water. Featuring a spacious layout with multiple outdoor living areas (540 sqft of porches), this property is designed to maximize your waterfront lifestyle. Enjoy breathtaking sunset views over the salt ponds, tranquil breezes, and the peaceful surroundings of this serene neighborhood. Whether you're looking for a weekend getaway or a year-round retreat, this is the ultimate location for enjoying all that the Florida Keys have to offer. Built to the latest building code, this home provides peace of mind with robust construction that makes insurance a breeze - the lowest rates possible - around $8000 annually. 15,000 pound boat lift, perfect for any kind of boating needs! Tenant occupied, notice and pre approval required for showings. Seller is a FL licensed real estate agent.

335 Pirates Rd, Little Torch
$894,000
3 Beds ⋅ 2 Baths ⋅ 620124 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 ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for coastal living. Built for both comfort and peace of mind, the home features a metal roof installed in 2018 along with impact-rated windows and doors throughout. Enjoy added privacy and nightly sunset views over the protected salt marsh directly across the street--an unspoiled natural backdrop that will never be developed. Boaters will appreciate the free-flowing, clear-water canal with excellent access to both the ocean and the bay. The private dock with a 7,000-lb side-lift boat elevator makes heading out for fishing, diving, or sunset cruises effortless. The spacious lot offers a large driveway, double covered parking, and ample room for boat trailers and additional vehicles. Downstairs, a full concrete pad and enclosed angler's room provide the perfect space for storing fishing gear, dive equipment, and all your island toys. Located near mile marker 28.5, Jolly Roger Estates is a peaceful, palm-lined waterfront community on the Atlantic side of Little Torch Key, offering direct access to Pine Channel and world-class boating, fishing, and diving at nearby Looe Key Reef. Just 24 miles from Key West, this exceptional property delivers the perfect blend of island tranquility and convenient access to dining, entertainment, and amenities--an ideal full-time residence, second home, or investment in the Florida Keys lifestyle.

437 Pirates Rd, Little Torch
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619868 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 off of the living room leading onto a sprawling deck overlooking the turquoise water. This home has a pool and is a spacious 2 Bedroom 1.5 Bath with a loft. Dock with 7,000lb. boat lift and storage enclosure.

257 La Fitte Rd, Little Torch
$2,100,000
5 Beds ⋅ 4 Baths ⋅ 619117 MLS
Pre-Construction Luxury Home | Jolly Roger Estates Introducing a rare pre-construction opportunity in the desirable waterfront community of Jolly Roger Estates. This CBS-built, fortress-like home is designed for durability, efficiency, and modern coastal living. The two-story floor plan offers 5 bedrooms, 4 bathrooms, and 2,886 square feet of living space, along with a spacious downstairs storage area--perfect for all your boating and outdoor gear. The property will feature a 10' x 23' swimming pool with an integrated jacuzzi, outdoor kitchen, and a TPO roof with a rooftop observation deck, ideal for taking in open water views, sunsets, and the surrounding Keys landscape. For boating enthusiasts, this home checks every box. The property will feature a 60' x 8' composite dock equipped with a 10,000-pound boat lift, set along deep, clear, flow-through canals with approximately 4 feet of draft-providing excellent accommodation for larger vessels and quick, easy ocean access with no bridges. Built with sustainability in mind, this Green Build Certified home includes features such as solar panels and a 1,000 gallon cistern, offering long-term value and reduced environmental impact. Conveniently located less than 5 minutes from restaurants, grocery stores, and shopping, and just 30 minutes from Key West, this property delivers the perfect balance of privacy, accessibility, and upscale waterfront living.

662 Blackbeard Rd, Little Torch
$1,349,000
3 Beds ⋅ 3 Baths ⋅ 619055 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 open water, making it ideal for fishing and island adventures. Designed for the Florida Keys lifestyle, the property features a private pool, tiki hut, and spacious outdoor entertaining areas overlooking the canal. Boaters will appreciate the dock and 14,000-lb boat lift, providing easy access for larger vessels. Whether you're seeking a full-time residence or a luxury island retreat, this home delivers the perfect blend of comfort, boating, and relaxed Keys living.

845 Pirates Rd, Little Torch
$1,299,999
3 Beds ⋅ 2 Baths ⋅ 617537 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 covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the upper-level. The main level of this Glenn Gray-designed, 1820 sq. ft. home has quartzite kitchen counters and abundant cabinets, comfortable living and dining areas, washer/dryer, and tile floors. The upper level has the third, primary bedroom with a small refrigerator in the ensuite bath, and another porch with views of neighborhood views and glimpses of Newfound Harbor. A convenient second staircase leads from the large back porch to the back yard and dock. Hardie plank siding, metal roof; some of the upper-level windows are impact-resistant; doors and remaining windows have shutters. Solar-assisted water heater. Although not currently in use, the 2,500-gallon rainwater cistern provides the potential of supplemental water for plants and washing vehicles.

28560 Doubloon Rd, Little Torch
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