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17287 Cayman Dr, Sugarloaf
$970,000
3 Beds ⋅ 2 Baths ⋅ 619597 MLS
Turn key canal front home on Lower Sugarloaf Key. This is a prime location that offers a tranquil setting with NO Route 1 noise, an amazing neighborhood, and a short 17 mile drive to Key West! Property has a large lot that will accommodate a pool, RV, and plenty of room for you to create your own personal oasis. Enjoy your unobstructed views of the adjoining nature preserve with amazing sunrises. The home has an open floor plan that welcomes you upon entry with natural light, warm colors, crown molding and tray ceiling. The split bedroom floor plan allows you total privacy for the master suite while providing comfort to your guests. The canal system offers easy boating access to world-class fishing and diving in the Atlantic Ocean and the Gulf. Imagine arriving at Marvin Key sandbar and the backcountry after a short boat ride. No worries, the nearby Sugarloaf Marina has everything you'll need to enjoy your excursions. There are many fabulous restaurants and coffee houses nearby to also enjoy; South Of The Seven, Square Grouper, Broil, Mangrove Mama's, Baby's Coffee, and Morning Joint to name a few. The home was built to 180 mph wind load standards, (impact-rated windows/doors), has Hardie-board exterior siding, a concrete dock, and low-cost flood insurance. The home is well maintained with multiple upgrades including a new metal roof in 2023. All of the stainless-steel appliances and washer and dryer are included in the sale. Don't wait and schedule your private tour today!

17287 Cayman Dr, Sugarloaf

1129 Hawksbill Ln, Sugarloaf
$950,000
2 Beds ⋅ 2 Baths ⋅ 620550 MLS
Located at the end of a quiet street in Sugarloaf Key, this 2 bedroom, 2 bath canal-front home is only two lots in from open water and offers open water views from the living room and large deck. Start the morning with coffee overlooking the ocean, then hop in the boat and be minutes from Bow Channel with easy access to both the ocean and Gulf side. Inside, the home feels open, warm, and comfortable with vaulted wood-beamed ceilings, a spacious great room, impact windows and doors, and a well-designed kitchen with granite counters, and a large island with extra seating and storage. The primary suite has its own upgraded ensuite bath, walk-in closet, canal views, and private screened balcony with additional stairs to the backyard. The guest bedroom is equipped with a Murphy bed to take your home office to guest ready in minutes. This home also has an additional large walk in, interior storage closet. The large lot offers the convenience of an RV hook-up, plenty of covered parking, shaded outdoor living space, a propane whole-house generator and a 68 ft. concrete dock. For those looking for peace, privacy, nature, and true Keys boating access, this Sugarloaf Key home checks all the boxes.

1129 Hawksbill Ln, Sugarloaf

146 Sugarloaf Dr, Sugarloaf
$935,000
3 Beds ⋅ 3 Baths ⋅ 618234 MLS
Canal-Front Home in Sugarloaf - Boat Lift Included - Enjoy the ultimate Keys lifestyle in this well-maintained 3-bedroom, 2-bath canal-front home in beautiful Sugarloaf Key. Located on a quiet street, this move-in ready property offers direct boating access and your own private dock with boat lift—perfect for easy access to both the Gulf and Atlantic with no bridges. Inside, the home features an open-concept layout with vaulted ceilings, a bright kitchen with stainless steel appliances, and generous living space filled with natural light. Motivated seller - all reasonable offers considered! Just 20 minutes from Key West, close to top-rated schools, dining, and outdoor recreation. Schedule your private showing today—opportunities like this don't last!

146 Sugarloaf Dr, Sugarloaf

17137 W Bonita Ln, Sugarloaf
$850,000
3 Beds ⋅ 2 Baths ⋅ 615651 MLS
Enjoy this ideal custom built Keys home located in beautiful Sugarloaf Shores! A very welcoming home with 3 bedrooms, 2 baths and a lovely enclosed porch with a captivating tong and groove ceiling. Attractive wood flooring throughout the living room, dining area and bedrooms with tile in the kitchen and baths. Two solid wide staircases lead up to the main entrance and another descending to decking on a sparkling wide canal great for swimming, fishing and boating or just relaxing. The home features a walkway 3/4 around the elevated house overlooking a fenced yard with plenty of room for a pool. Downstairs two paved driveways lead to a spacious enclosed storage area for all of your toys and tools, Sugarloaf Shores is known for its Blvd walking path, spacious lots and community socials along with a great location for proximity to the charm and culture of Key West and Big Pine Key. Come see this piece of Paradise and make it your home! Easy to show!

17137 W Bonita Ln, Sugarloaf

17245 Jamaica Ln, Sugarloaf
$825,000
3 Beds ⋅ 2 Baths ⋅ 617093 MLS
Tucked along a quiet canal in Sugarloaf Shores, 17245 Jamaica Lane captures the essence of easy Keys living. This waterfront retreat offers direct access to open water and all things salt life—paddleboarding, kayaking, the iconic jumping bridge, and world-class cycling right out your door. Set on a generous lot, this elevated 3-bedroom, 2-bath home blends laid-back island charm with modern comfort. Inside, 1,248 square feet of light-filled space feature granite countertops, quality appliances, and thoughtful storage throughout. The primary bedroom includes a private bath, while two guest rooms offer flexibility for visitors, a home office, or creative space. A rear balcony overlooks the canal—perfect for morning coffee, evening breezes, or watching the tide roll in. Below, a spacious garage and covered area offer room for storage, a workshop, or shaded lounge space. There's ample parking for vehicles, a boat trailer, or RV, and plenty of room to add a pool or expand your outdoor entertaining area. With quick access to world-class fishing, sandbars, and snorkeling, this home is a true boater's haven. Whether you're looking for a full-time residence, weekend escape, or investment property, 17245 Jamaica Lane delivers relaxed comfort and adventure-ready living in one of the Lower Keys' most desirable neighborhoods—just a short drive from the vibrant energy of Key West.

17245 Jamaica Ln, Sugarloaf

19611 Tequesta St St, Sugarloaf
$810,000
3 Beds ⋅ 3 Baths ⋅ 617787 MLS
Relaxed living at its finest on Sugarloaf Key. This peacefully landscaped 10,000 sq ft double parcel offers a 3 bedroom, 2.5 bath, 1564 sq ft stilted home, with in ground pool, generous off street parking, storage and sheds. Enjoy your morning coffee or afternoon cocktail on one of 3 sprawling porches this home offers. This open concept home provides endless natural light, high ceilings, wooden floors, whirlpool jacuzzi spa tub, walk in primary closet and peaceful mood lighting throughout (Govee Smart System). The outdoor area offers abundant opportunities for entertaining, hobbies, housing your motorized toys or expanding your footprint with a separate structure. (sample plans available upon request). Neighborhood has private beach and boat ramp, picnic area, and kayaks for use.

19611 Tequesta St St, Sugarloaf

17326 Jamaica Ln, Sugarloaf
$750,000
2 Beds ⋅ 2 Baths ⋅ 618733 MLS
Welcome to your slice of Lower Keys paradise--just 17 miles from Key West yet worlds away from the hustle. This elevated 2-bedroom, 2-bath home sits on a generous lot in a fantastic neighborhood, offering the perfect blend of comfort, style, and island living. Inside, vaulted ceilings and impact windows fill the home with natural light and breezy tropical charm. An elevator makes access effortless, and a whole-home generator keeps life running smoothly no matter the weather. Enjoy the peace of mind of the newer AC! Downstairs, you'll find an expansive storage area ideal for a workshop, gear room, or the ultimate hobby space--plenty of room for tools, toys, and all the essentials of Keys life. Step outside and access the convenience clean canal water surrounded by lush, vibrant landscaping that feels like your own private botanical garden. Enjoy gorgeous views of the natural protected preserve right across the canal allowing for phenomenal sunsets. The all-weather decking is made for morning coffee, sunset cocktails, and everything in between. Boaters and water lovers will appreciate the dedicated skiff launch, making it easy to slip out for a day on the water whenever the mood strikes. Boaters will love being less than a 10-minute ride to open water, making sunset cruises, reef fishing, and sandbar days incredibly easy. Enjoy a scenic ride under the historic Jumping Bridge as you head out -- a true local favorite and iconic Keys experience. Whether you're looking for a full-time residence, weekend escape, or investment opportunity, this home delivers the lifestyle buyers come to the Florida Keys for: sunshine, salt air, and quick access to the water. Relax under the palms, tinker in your workshop, or head out for a quick trip to Key West or Marathon, this home delivers the laid-back tropical lifestyle people dream about. It's island living--comfortable, convenient, and full of character. Your Sugarloaf slice of paradise awaits.

17326 Jamaica Ln, Sugarloaf

17230 Angelfish Ln, Sugarloaf
$687,500
616647 MLS
Build Your Dream Home in Sugarloaf Shores! Don't miss this rare opportunity to own a waterfront lot in the desirable Sugarloaf Shores! This high and dry, cleared 8,165 sq. ft. parcel offers a fresh canvas for your vision of paradise in the Florida Keys. The property features a brand-new concrete seawall, perfect for the boating enthusiast, with direct access to both the Atlantic Ocean and the Gulf of Mexico. Permits for construction have already been awarded and await final release upon plan updates by the builder, saving valuable time in your development process. Just one lot in from Sugarloaf Sound, this prime location offers the potential for stunning open-water views, making it an ideal site for your custom home. Located just 15 minutes from the vibrant attractions of Key West to the south and the serene natural beauty of Big Pine Key to the north, this property perfectly balances convenience and tranquility. Whether you're looking to design your dream home or an investment property, this lot is a boater's dream and a unique chance to create your personal paradise in the Florida Keys. *Seller is a licensed FL Realtor

17230 Angelfish Ln, Sugarloaf

19591 Navajo St, Sugarloaf
$649,000
2 Beds ⋅ 2 Baths ⋅ 619153 MLS
INDIAN MOUNDS SPECIAL!!!! Two balconies with ocean views and a hot tub to enjoy them with!!! Just one block from the private community boat ramp, this elevated 2 bed, 2 bath home sits on a large oversized corner lot. There is plenty of room for parking your toys and a downstairs enclosure for additional storage. Hardibacker siding and a metal roof provide peace of mind. Upon entering, you'll find the spacious living room, access to the first balcony with a hot tub, the kitchen, laundry closet, guest room and bathroom with tub. Up the spiral staircase, you'll find the master suite and the door to the second balcony. Local school is walking distance for kids. Local neighborhood hosts a multitude of annual events such as July 4th fireworks, in addition to Holiday and Halloween block parties. Neighborhood boat ramp provides a 15 minute boat ride to Gulfside Sandbars and SUNSETS!!!! Dolphins, Lobster, Stone Crab, Tarpon, Permit, Bonefish, Snapper, Sea trout, and Rays are all prevalent in Bow Channel, right near the ramp. Call today for your private showing! It would be my pleasure to help you join this amazing community.

19591 Navajo St, Sugarloaf

19264 Acosta Trl, Sugarloaf
$475,000
2 Beds ⋅ 2 Baths ⋅ 619336 MLS
Prime Sugarloaf Key Opportunity - Over 2 Acres of Privacy & Potential Nestled on highly desirable Sugarloaf Key, this elevated 2-bedroom, 2-bath home sits on over 2 acres of lush, private land--offering a rare opportunity to create your own piece of paradise in the Lower Florida Keys. There is a bonus room that can be used as a 3rd bedroom The existing stilted structure provides a solid footprint and a starting point for those with vision. Whether you choose to renovate and reimagine the current home or build a custom coastal retreat, the possibilities here are truly exceptional. Surrounded by natural beauty and mature vegetation, the property offers unparalleled privacy while still being conveniently located less than 20 minutes from Key West. The expansive lot allows ample space for a new build, outdoor living areas, storage for boats or RVs, and more--making it ideal for those seeking both seclusion and flexibility. There is a 12,000 gallon cistern as well. Opportunities like this--large acreage in a prime location--are increasingly rare in the Keys. Bring your contractor, your architect, and your imagination. Key Features: 2 Bedrooms / 2 Bathroom elevated home Over 2 acres of land Exceptional privacy and natural surroundings Endless potential: renovate or build new Located in sought-after Sugarloaf Key. Buyer to verify all details.

19264 Acosta Trl, Sugarloaf