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, within the stunning Monroe County. This charming subdivision is the perfect blend of tropical paradise and serene living, making it an ideal choice for those seeking a slice of paradise in the Florida Keys.

Jolly Roger Estates boasts a variety of homes for sale, each offering unique architectural styles and features that cater to diverse tastes. Whether you’re looking for a cozy waterfront retreat, a spacious family home, or a modern getaway, you’ll find it here. Many properties in this vibrant community come equipped with lush landscaping, private docks, and breathtaking views of the sparkling waters that surround the area.

Living in Jolly Roger Estates means embracing the laid-back Florida lifestyle. Residents enjoy access to a plethora of outdoor activities, from boating and fishing to kayaking and snorkeling in the nearby coral reefs. The community's proximity to local parks, beaches, and nature trails ensures that adventure is always just around the corner.

With its friendly atmosphere and close-knit community, 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 next chapter in life. Whether you’re looking to retire, invest, or simply escape to a warmer climate, Jolly Roger Estates offers an unparalleled lifestyle that is hard to resist. Come experience the magic of Florida living!

Newest Jolly Roger Estates (28.5) Homes for Sale

569 Pirates Rd, Little Torch
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 621484 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 wetlands and inviting deck and Tiki! 3Bd/2Ba home features quartz counters, tile floors throughout impact-resistant windows & doors, metal roof, paver drive, and two storage enclosures below. 50 ft wide flow through canal and 15,000 lb boat lift.

569 Pirates Rd, Little Torch
400 La Fitte Rd, Little Torch
$939,000
2 Beds ⋅ 2 Baths ⋅ 621295 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 knowing the ocean is just moments away. Welcome to 400 La Fitte Road, a furnished canal-front home in Little Torch Key's desirable Jolly Roger Estates, ideally located on the oceanside at Mile Marker 28.5. Positioned on a spacious corner lot, this approximately 1,080-square-foot home offers two bedrooms, two bathrooms, durable CBS construction, tile flooring, accordion shutters, and a 40-foot concrete dock. Covered parking, garage and storage space, plus room for an RV or boat trailer, make it especially well suited for the relaxed Keys lifestyle. Boaters will appreciate the convenient ocean access, approximately three feet of reported control depth, and the neighborhood's community boat ramp. Why it stands out for retirement or investment: Offered furnished for an easier transition 28-day minimum rentals offering potential monthly income Quieter residential atmosphere without frequent weekly guest turnover Municipal sewer and FKAA water Spacious corner lot with room for recreational vehicles Close to Big Pine Key's shopping, dining, services, and National Key Deer Refuge Approximately 26-27 miles from Key West International Airport--normally about a 38-minute drive, depending on traffic Whether you envision a peaceful retirement retreat, a Florida Keys getaway, or an income-producing investment near Key West, this property offers the flexibility to enjoy it now while keeping future possibilities open. Come furnished. Bring the boat. Start living the Keys lifestyle.

400 La Fitte Rd, Little Torch
335 Pirates Rd, Little Torch
$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
257 La Fitte 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
662 Blackbeard 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
28560 Doubloon 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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