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$1,595,000
3 Beds ⋅ 3 Baths ⋅ 620823 MLS
Experience classic Florida Keys waterfront living in this spacious canal-front retreat on Sugarloaf Key, offering boating access, expansive indoor-outdoor living, and just a short drive to Key West. 3,000 square feet of finished living space including 4 bedrooms and 3 baths. Situated on a wide canal with ample room for a future dock, offering the opportunity to create your own boating paradise. The massive chef's kitchen features copious marble countertops, abundant cabinetry, generous seating, and opens seamlessly into the impressive great room--ideal for entertaining family and friends. The open concept living spaces open onto a large canal-side deck that extends your living space outdoors. The spacious primary suite offers tranquil canal views and a spa-inspired bath with a soaking tub positioned to take in the waterfront scenery. A skylit bonus room offers endless possibilities as a fitness room, artist's studio, or sunroom. The nicely landscaped 13,000-square-foot property offers a circular drive, mature tropical plantings, and abundant parking for guests, boats, and recreational vehicles. Whether you're seeking a full-time residence, seasonal escape, or exceptional waterfront investment, this distinctive Sugarloaf Key home offers the space, setting, and Florida Keys lifestyle you've been waiting for.

182 Venetian Way, Sugarloaf
$749,900
3 Beds ⋅ 2 Baths ⋅ 620391 MLS
3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size laundry room and on-demand hot water heater. Large master bedroom with en-suite bathroom, dual sink vanity and large walk-in closet. 2 guest bedrooms and full guest bathroom. Large covered porch off the main living/kitchen area, fenced on 3 sides. Newer downstairs storage room, room for boat/trailer; boat ramp is one street over and you are less than a mile from Sugarloaf Elementary and Middle school. Quick access to Key West and bases.

19543 Navajo St, Sugarloaf
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 619901 MLS
Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, fishing, and the easygoing Keys lifestyle right at their doorstep. Set on a quiet street just 15 minutes from Key West, this sturdy concrete 2 bedroom, 2 bath home offers southern exposure overlooking the canal, quick access to open water, and inviting outdoor spaces designed for relaxing after a day on the water. Spend mornings on the screened porch, enjoy afternoon breezes from the private balcony off the primary bedroom, and make the most of a waterfront setting that brings the best of island living together in one place. Inside, the home features an open floor plan with tile floors, high ceilings, a bright living and dining area, and a kitchen with a breakfast bar. The main bedroom includes a walk-in closet and direct balcony access, creating a private spot to enjoy the tropical surroundings. Outside, boaters and water lovers will appreciate the approximately 40-foot dock, dedicated skiff launch/ramp, canal frontage, and quick route to open water. The dock and waterfront setup provide a convenient place to keep a boat, launch a skiff, or head out for a day on the water with ease. The property also offers a garage and carport area, giving plenty of room for parking, storage, and Keys gear. Located in Sugarloaf Shores, this home offers peaceful island living with convenient access to dining, entertainment, and world-class recreation in nearby Key West.

17286 Jamaica Ln, Sugarloaf
$950,000
3 Beds ⋅ 2 Baths ⋅ 619875 MLS
On a quiet dead-end street in the highly sought-after Sugarloaf Shores community, sits this fully renovated tropical retreat thats reminiscent of something straight out of a secret garden. Set on an oversized, gated and partially fenced parcel spanning over a quarter acre, this rare non-waterfront property offers the kind of lush green space that's nearly impossible to find in the Florida Keys. Towering old-growth foliage, vibrant established plantings, fresh new landscaping, and newly laid sod create a private, enchanted oasis where every corner invites you to slow down and stay awhile. Built in 1981 of solid concrete block construction and elevated on slab, this beautifully reimagined 3-bedroom, 2-bathroom home offers 1,548 square feet of airy, light-filled living space with bright neutral finishes and thoughtful details throughout. Every inch has been meticulously renovated, blending modern comfort with effortless island charm. Designed to embrace indoor-outdoor living, the property features multiple lanais and entertaining spaces perfect for morning coffee beneath the palms, sunset dinners with friends, or quiet afternoons surrounded by tropical serenity. The expansive lot offers endless opportunity for future enhancements -- envision a resort-style pool and tiki hut, a greenhouse, outdoor kitchen, play space for the kids, or all of the above. There's room here to truly create your dream Keys compound. Downstairs, nearly 400 additional square feet of enclosed storage and utility space adds incredible flexibility, while the paved 3-car carport with lighting and built-in workspace could easily be transformed into the ultimate outdoor entertaining kitchen or hobby space. Beloved Sugarloaf Shores provides peaceful island living with a scenic miles-long paved path, a laid-back Lower Keys atmosphere, and sought-after school district -- all just 15 minutes from exciting Key West. Rare Keys privacy, greenery, and possibility you may never want to leave.

123 Venetian Way, Sugarloaf
$2,299,999
3 Beds ⋅ 3 Baths ⋅ 619431 MLS
Experience the best of waterfront living in this brand-new home on Lower Sugarloaf Key. Thoughtfully designed and meticulously built, this 3-bedroom, 2.5-bath residence offers 2,288 square feet of modern coastal comfort. Situated on an expansive 16,445-square-foot lot, the property features a private seawall for direct boating access and a sparkling pool perfect for relaxing after a day on the water. The home's elevated design provides a generous covered area beneath, ideal for parking multiple vehicles, storing watercraft, or hosting outdoor gatherings. Inside, the open-concept layout seamlessly connects the living, dining, and kitchen spaces, all oriented to capture natural light and water views. The primary suite is a serene retreat with a spa-inspired bath, while two additional bedrooms offer flexibility for guests or family. Located just minutes from Key West yet tucked away in the quiet beauty of Lower Sugarloaf, this lushly landscaped home is an exceptional opportunity to enjoy the Florida Keys lifestyle. *Adjacent Vacant Lot also available. **Seller is a licensed FL Realtor

17210 Angelfish Ln, Sugarloaf
$998,000
3 Beds ⋅ 2 Baths ⋅ 619159 MLS
Botanical Waterfront Compound ~ 3 bedroom/2 bath elevated CBS home on a fenced half-acre, just 20 minutes from Key West and near Sugarloaf schools. Potential for a fourth (4) bedroom, office, hobby room, etc.. Features a swimming pool with full screened outdoor patio surround, and lush tropical landscaping with palms, orchids, agave, and mature mango trees. Two cistern tanks for watering plants, washing boats & vehicles @ approximately 2,500 gallons each tank. Enjoy quick boating access to the Gulf side for premier tarpon, bonefish and permit flats, and close proximity to Sugarloaf Marina for shallow draft outboard vessels. This canal-front property includes a 30' composite dock with fish cleaning station and launching for kayak or paddle board. Additional highlights: detached carport/workshop, storage shed, and large cistern for irrigation and cleaning boats and vehicles etc.. **VA assumable loan @ 2.25% - VA must approve** **VA Assumable Loan @ 2.25% may be a possibility to a qualified VA Buyer** SELLER'S INSURANCES: FLOOD $2,318, WIND $6,683, HOMEOWNERS $2,159.75 **Canal entrance is 3'+/- at low tide**Shallow draft outboard vessels**Buyer to verify if suitable for Buyers' boating needs**

83 Sugarloaf Dr, Sugarloaf
$2,375,000
5 Beds ⋅ 4 Baths ⋅ 617951 MLS
Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views. The primary suite is a private sanctuary, highlighted by a wall of windows that greets each morning with sweeping vistas of the open Atlantic—an ever-changing canvas of blues that defines life in the Florida Keys. Throughout the home, wall-to-wall water views create a seamless connection between indoor comfort and the surrounding seascape, offering multiple spaces to relax, entertain, and soak in the coastal atmosphere. Set on an impressive 12,500-square-foot lot, the property provides ample room for outdoor living, recreation, and plenty of room for a pool. Boaters will appreciate the 120-foot concrete seawall with davits, delivering effortless access to world-class fishing, diving, and the iconic Lower Keys sandbars. The elevated design allows the entire lower level to transform into an expansive open-air lounge and entertainment area, complemented by a generous storage room for all your boating and island gear, plus abundant parking. Located in one of the Lower Keys' most sought-after neighborhoods, this peaceful waterfront escape is just 15 minutes from Key West, offering the perfect balance of privacy and convenience. Schedule your private showing today—available in person or via live video—and discover the essence of luxury island living.

205 S Point Dr, Sugarloaf
$899,000
3 Beds ⋅ 2 Baths ⋅ 618853 MLS
Set on over an acre of land, 19267 Hansen Trail is a truly one-of-a-kind property where modern luxury meets refined homestead living. Offering nearly 2,000 square feet of beautifully remodeled living space, this 3-bedroom, 2-bathroom residence has been thoughtfully upgraded with high-end finishes, all new impact windows and doors, and smart-home conveniences throughout. The open-concept design creates a seamless flow from the spacious living room into the designer kitchen and adjoining bonus space -- perfect for entertaining, working from home, or creating a private retreat -- all leading effortlessly to the expansive backyard. The oversized primary suite serves as a true sanctuary, complete with a spa-inspired en suite bathroom and a generous walk-in closet. Every detail has been carefully considered, including towel warmers in both bathrooms, automatic blinds on every window, and a smart refrigerator integrated into the modern kitchen. Built with durability and peace of mind in mind, the home features a whole-house generator and three large propane tanks -- ensuring reliability and comfort year-round. With ample space to expand, garden, entertain, or simply enjoy the privacy of acreage living, this property offers a rare opportunity to enjoy both luxury upgrades and the freedom of wide-open space. Schedule your private showing today and experience everything 19267 Hansen Trail has to offer.

19267 Hansen Trl, Sugarloaf
$8,995,000
6 Beds ⋅ 5 Baths ⋅ 617329 MLS
Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach — a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and diving. A protected 6-boat basin with room for extra boats is the centerpiece of the waterfront, complete with 25K and 16K lifts, a boat ramp, sandy beach, lookout point, and composite observation deck. After a day on the water, unwind in the lagoon-style saltwater pool with heater, chiller, and custom water features. The expansive tiki bar includes TVs, True refrigerator/freezer drawers, and an ice machine—perfect for effortless outdoor entertaining. Additional features include a firepit, private sandy beach, and a full outdoor kitchen equipped with built-in BBQ, Viking appliances, and True refrigeration. The upper level offers a bright and open Great Room with sweeping ocean views, a spacious dining area, and a chef's kitchen with stainless appliances. Two covered verandas provide ideal spaces for taking in the breezes and panoramic vistas. The primary suite features an office, en suite bath, walk-in closet with laundry, sunroom, and loft. Two additional upstairs guest rooms comfortably accommodate visitors, while the separate downstairs living area offers three more guest bedrooms for privacy and flexibility. Designed for hosting and convenience, the home is equipped with a Sonos sound system, property-wide Wi-Fi, abundant storage, a two-car garage with fishing lockers, and generous parking along a winding paver driveway. Lush, mature landscaping surrounds the property, creating a serene and secluded Sugarloaf Key retreat. Call for more information today!

16750 Old State Road 4a, Sugarloaf
$5,200,000
4 Beds ⋅ 4 Baths ⋅ 618184 MLS
Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound. Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT impact windows/doors, and Hardi board siding. Inside, enjoy a sunlit open-concept floor plan with soaring ceilings, a gourmet kitchen with quartz counters, premium stainless appliances, gas stove, a hidden butler's pantry, and a waterfront Bedroom wing, all oriented to frame the water from every room. Step outside and immerse yourself in resort-style living with a heated and chilled waterfront pool, soothing spa, hot tub, invigorating cold plunge, and a fire pit encircled by flickering tiki torches to gather with friends and family while sipping cocktails as the sun melts into the horizon. Lounge on the expansive covered porch while enjoying views of the peaceful nature preserve for incredible bird watching, and a setting that offers total privacy and serenity. Boaters will love the protected canal access with 2 boat lifts (8K & 12K lbs), just minutes from open water. Additional features include a 4-car garage with EV charger, covered RV Tiki with 50 amp service, whole-house 35kW generator (750-gal tank), whole house water softening system and Sonos throughout, including garage and outdoor zones. Whether you're seeking a private sanctuary, a trophy lot, or the ultimate Florida Keys lifestyle, Blue Sky Pointe delivers. This is the most premiere lot on Sugarloaf Key — a once-in-a-lifetime opportunity.

17013 Coral Dr, Sugarloaf
$19,750,000
6 Beds ⋅ 7 Baths ⋅ 617534 MLS
RARE PRIVATE SANDY BEACH | OCEANFRONT ESTATE | 30 MINUTES TO KEY WEST A truly extraordinary opportunity on coveted Sugarloaf Beach--over 5 acres of private oceanfront property offering endless open-water views, exceptional privacy and a rare natural sandy beach in the Lower Keys. This remarkable estate includes two County-recognized residential dwelling units with an established history of permitted vacation-rental use, creating a valuable combination of existing residential rights, income potential and future redevelopment opportunity. The main residence offers 4 bedrooms and 4 bathrooms, complemented by a second 2-bedroom, 2.5-bath residence, currently configured as luxury vacation rentals. A newly reconstructed 430-foot dock with stainless-steel pilings, stainless-steel support beams and composite decking provides exceptional boating access, with approximately 5-foot draft accommodating larger vessels. World-class fishing, diving and boating begin at your doorstep, with American Shoal Lighthouse approximately five miles offshore. A recent professional environmental and development review identifies existing developed and disturbed areas as particularly valuable for future redevelopment and notes potential to enlarge, replace or substantially reconfigure the two existing residences, subject to applicable approvals. The adjoining vacant parcel also contains a preliminary upland opportunity area identified for further development evaluation, adding another compelling dimension to this exceptional offering. With its private beach, expansive open-water setting, established residences, vacation-rental history and substantial waterfront infrastructure, this is a rare opportunity to create an extraordinary private compound or reimagine an iconic oceanfront retreat in one of the Florida Keys' most secluded settings. Future development and redevelopment are subject to applicable governmental approvals, environmental requirements and permitting.

15760 Old State Road 4a, Sugarloaf
$2,849,000
3 Beds ⋅ 2 Baths ⋅ 618874 MLS
Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid house for the gardening enthusiast. The main living level showcases a stunning Great Room with soaring tongue-and-groove ceilings and panoramic water views. The open kitchen overlooks Sugarloaf Sound and offers bar seating, stainless appliances, and gas range. A dining area with Dade County Pine accent wall adds warmth and character. The entire second floor is devoted to the private Primary Suite retreat, complete with walk-in closet, sitting room, and spectacular water views for morning coffee with the sunrise and evenings watching the Keys' famous sunsets. Outdoor living is exceptional with a waterfront heated and chilled pool, covered lanai for entertaining, outdoor shower, tiki hut, and private dock with 12,000 lb boat lift offering easy open water access. Every evening, the sky ignites in gold and crimson as the sun melts into Sugarloaf Sound. This is not just a home, it is a front-row seat to one of the Florida Keys' most extraordinary natural performances.

17041 Marlin Dr, Sugarloaf
$3,899,000
4 Beds ⋅ 3 Baths ⋅ 618713 MLS
Positioned on a rare west facing point lot with 270 ft of sparkling open water frontage on Sugarloaf Sound, this fully reimagined 3 Bedroom 3 Bathroom estate captures breathtaking sunset views across endless turquoise waters. Privately set on a gated 17,000 SF lot, the property lives like a private island compound framed by swaying palms, lush tropical landscaping, and the endless blue waters of the sound. The CBS constructed residence is complemented by a new aluminum standing seam metal roof and a complete set of impact windows/doors, offering exceptional structural integrity paired with refined island sophistication. Walls of glass flood the expansive open concept living area with natural light and showcase panoramic water views from nearly every vantage point, immersing the home in its spectacular waterfront setting. The coastal modern interior features tile plank flooring throughout, clean architectural lines, and a serene coastal palette that reflects its tropical surroundings. The chef's kitchen is anchored by an oversized waterfall edge island, custom cabinetry, high end stainless appliances, wine refrigeration, and designer lighting, all positioned to embrace the open water backdrop. The spacious primary suite overlooks the sound and serves as a private retreat, featuring a spa inspired bath with dual vanities, custom tile work, and a frameless glass walk in shower. Two additional ensuite guest bedrooms are beautifully appointed, offering privacy and comfort for family and visitors. Outdoors, the brand new concrete pool and inviting tiki hut create a true resort style setting, complemented by expansive lawn space rarely found in the Keys. After a day of world class fishing and diving in the Lower Keys, dock your vessel on the 14,000 lb boat lift, an exceptional enhancement to the waterfront lifestyle. Completely renovated and move in ready, this extraordinary estate defines sophisticated island living at its finest.

17015 W Wahoo Ln, Sugarloaf