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$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
$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
$1,710,000
4 Beds ⋅ 2 Baths ⋅ 617353 MLS
Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy. Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring by paddleboard or kayak, or heading out on your boat to world-class fishing and diving, this location makes it effortless. The backyard is designed for relaxation and connection, featuring a pool, spa, and multiple outdoor patio areas, all surrounded by lush, mature tropical landscaping. Inside, the home features a renovated kitchen, bright open living spaces, and a large enclosed back porch that extends your living area and overlooks the pool, spa, and canal. With four bedrooms, generous square footage, and seamless indoor-outdoor flow, the home is ideal as a primary residence, seasonal getaway, or investment property with tremendous upside. Located just minutes from Key West yet surrounded by the peace and natural beauty of Sugarloaf, this property offers the best of both worlds—space, privacy, and direct water access that's hard to find, along with the freedom to create your ideal island retreat.

1481 Sugarloaf Blvd, Sugarloaf
$1,950,000
2 Baths ⋅ 617065 MLS
Renovated Commercial Space - The Alamo Building, Sugarloaf Key (MM 20) Prime, newly updated commercial space available on Sugarloaf Key, directly across from Mangrove Mama's Restaurant. This high-visibility property on US-1 has been completely renovated inside and out, offering a clean, modern look with flexible space suited for a wide range of uses. Currently operated as a welcome center for Sugarloaf Key RV Resort and Cottages, the property is ideal for retail, showroom, professional services, fitness/yoga studio, coffee/juice bar, or even restaurant spaces (no commercial kitchens currently on premises). The layout supports both customer interaction and back-office functionality, with open areas, private offices, and refreshed restrooms. A spacious outdoor patio provides even more possibilities. This property offers excellent US-1 exposure with a steady flow of daily traffic, making it ideal for attracting customers and visibility. There is ample paved parking with convenient highway access, ensuring easy entry for clients and deliveries. The building includes approximately 2,520 square feet of usable commercial space situated on a 31,000-square-foot lot, offering flexibility for a variety of business operations. It is located just minutes from Key West and Big Pine, in the prime, central Lower Keys corridor. Buyer to verify zoning and permitted uses with Monroe County.

19980 Overseas Hwy, 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
$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