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, a hidden gem nestled in the enchanting Little Torch Key, Florida, within the picturesque Monroe County. This charming subdivision is a paradise for those seeking a serene waterfront lifestyle, where the gentle sway of palm trees meets the soothing sounds of the ocean.

Jolly Roger Estates boasts an impressive selection of homes, many of which feature stunning canal front waterfront properties. Imagine waking up to the tranquil views of sparkling waters right outside your window, with the possibility of hopping on your boat for a day of adventure on the beautiful Florida Keys. The canal access provides not only a gateway to endless aquatic activities like fishing, kayaking, and paddleboarding but also the perfect backdrop for idyllic sunset views that will leave you in awe.

The community is characterized by its friendly atmosphere and well-maintained properties, making it a perfect haven for families, retirees, or anyone looking to escape the hustle and bustle of city life. Residents enjoy a laid-back lifestyle, where neighbors become friends, and weekend barbecues turn into cherished memories.

With its unique blend of natural beauty and convenient access to local amenities, Jolly Roger Estates is not just a place to live; it's a lifestyle to embrace. Whether you’re looking to invest in a vacation home or a permanent residence, this enchanting community offers the best of Florida living. Come explore the magic of Jolly Roger Estates and discover the waterfront home of your dreams!

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

$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
$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
$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
$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
$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
$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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