Refine Search
Map
Sort by
$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
$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
$3,199,000
4 Beds ⋅ 4 Baths ⋅ 618532 MLS
Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable saltwater swim. Outdoor lighting perfects this entire property along and under the dock and seawall as well. A new higher end fiberglass pool and spa made by Latham which are built with double thick fiberglass complete with heater and chiller is just waiting for you to enjoy after a day on the water or an evening of entertaining. The adjoining new tiki hut, complete with a NewAge summer kitchen, a dining area and ready for happy hours and fish tales. The bar and lounging area located across from the tiki hut provides a comfortable lounging area complete with a nice storage area. Pavers adorn all the open spaces surrounded by new exquisite, lush landscaping maintained by a 5-zone irrigation system. A new standing seam metal roof was installed in 2024. Oh and did I mention a real fire pit. This gorgeous home is all about being outdoors and enjoying the Florida Keys tropical ambiance. The main living area has an open kitchen concept with a center island, gas stove, new appliances, and dining table. Guest bedroom is on the main floor with a full bath and walk in shower. Upstairs has two master suites, one with a stand-alone tub and walk in shower and the other with a walk-in shower only. Two of the bedrooms have balconies overlooking this peaceful, delightful, property. All the furniture is brand new and comes included with the purchase. With the proximity to Key West, and all the excitement and nightlife and the world class fishing and diving out your back door, the world is your oyster in this Fabulous Florida Keys slice of paradise. Don't let this one get away.

17183 Coral Dr, 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
$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