Jolly Roger Estates (28.5) Homes with Canal Front Waterfront features

Jolly Roger Estates (28.5) Homes with Canal Front Waterfront features

Welcome to Jolly Roger Estates, an idyllic subdivision nestled in the heart of Little Torch Key, Florida, within the stunning Monroe County. This charming community is a hidden gem that offers a perfect blend of natural beauty, tranquil living, and waterfront access, making it an ideal place for those seeking a slice of paradise.

Jolly Roger Estates boasts an impressive array of homes, many of which feature breathtaking canal-front waterfront properties. Imagine waking up each morning to the gentle sounds of water lapping against your dock, with the sun rising over the serene canals that weave through this picturesque neighborhood. These homes are designed for those who appreciate the joys of waterfront living, offering direct access to the crystal-clear waters of Florida Bay and the Atlantic Ocean beyond.

The subdivision is not just about beautiful homes; it’s a vibrant community where neighbors become friends. Residents enjoy a laid-back lifestyle, complete with opportunities for boating, fishing, and exploring the natural wonders of the Florida Keys. With its lush tropical landscaping and friendly atmosphere, Jolly Roger Estates provides a welcoming environment for families, retirees, and everyone in between.

Whether you’re looking for a cozy getaway or a permanent residence, Jolly Roger Estates offers a unique opportunity to own a piece of paradise. With its stunning canal-front homes and the allure of waterfront living, this subdivision is truly a dream come true for anyone who loves the beauty of the Florida Keys. Come and discover your new home in Jolly Roger Estates, where every day feels like a vacation!

Newest Jolly Roger Estates (28.5) Homes with Canal Front Waterfront features

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
28525 Jolly Roger Dr, Little Torch
$800,000
620926 MLS
Rare actively permitted waterfront homesite with existing concrete seawall/dock on Little Torch Key with exceptional boating access, approved engineered house plans, and protected salt-pond and nature-preserve views across the street. The property is offered with an active Monroe County building permit and approved plans for an elevated concrete 3-bedroom, 2-bath residence with approximately 1,818 square feet of air-conditioned living area and nearly 500 square feet of covered porches. The home was thoughtfully designed and engineered by respected longtime local engineer Carl H. Schror, P.E., with an open great-room layout and generous outdoor living suited to the Florida Keys lifestyle. In the current ROGO and permitting environment, the active permit, completed engineering, surveys, environmental review, and county-approved plans represent substantial value. A buyer may proceed with the approved home or explore revisions to create a more personalized design, subject to Monroe County approval. As a longtime Lower Keys builder and developer, the listing broker can attest that design, engineering, ROGO, and county plan review are often among the most expensive, uncertain, and time-consuming parts of building in the Keys. Much of that initial work has already been completed here. Approximately 4 feet of controlling depth provides excellent boating, with immediate access to Pine Channel and quick access to both the Atlantic Ocean and backcountry. Premier fishing, diving, snorkeling, and sandbar destinations are within easy reach. The homesite offers canal frontage and a seawall at the rear, while the front overlooks salt ponds and protected natural land rather than another residence. Quiet Little Torch Key location convenient to restaurants, grocery stores, marinas, boat ramps, and everyday services. Please verify permit status, approved plans, controlling depth, and any proposed plan modifications directly with Monroe County and the appropriate profe

28525 Jolly Roger Dr, Little Torch
28587 Peg Leg Rd, Little Torch
$595,000
620488 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 square-foot, four-bedroom, three-bathroom residence with a rooftop terrace offering open ocean views. Dock and full architectural plans are included. A local builder is ready to build to the buyer's specifications, with price and terms to be negotiated. Located on Little Torch Key, just 28 miles from Key West, with quick no-bridge access to open water. Buy now, build on your timeline.

28587 Peg Leg Rd, Little Torch
28597 Peg Leg Rd, Little Torch
$595,000
620486 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 drawn for a 3,809 square-foot, four-bedroom, four-bathroom residence with open water views. A separate dock permit is also in process -- Permit #R-DOCK-2025-0302 -- along with full architectural plans, all included in the purchase. A local builder is ready to build to the buyer's specifications, with price and terms to be negotiated. Located at Mile Marker 28.5 on Little Torch Key, just 28 miles from Key West, with quick no-bridge access to open water. Buy now, build later!

28597 Peg Leg 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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