Sugarloaf Key Real Estate

Sugarloaf Key Real Estate

Welcome to Sugarloaf Key, a hidden gem nestled in the heart of the Florida Keys, within Monroe County. This idyllic island offers a unique blend of natural beauty, tranquility, and vibrant local culture, making it a perfect destination for those seeking an escape from the hustle and bustle of everyday life.

Sugarloaf Key is characterized by its lush landscapes, crystal-clear waters, and stunning sunsets that paint the sky in breathtaking hues. The island is renowned for its diverse wildlife, including tropical birds and marine life, making it a paradise for nature enthusiasts and outdoor adventurers. With its proximity to the Florida Keys National Marine Sanctuary, residents and visitors alike can enjoy world-class snorkeling, diving, and fishing right at their doorstep.

The community on Sugarloaf Key is warm and welcoming, with a laid-back atmosphere that encourages a strong sense of camaraderie among neighbors. You'll find charming local shops, delightful eateries, and an array of recreational activities that cater to all ages. Whether you’re kayaking through the mangroves, biking along scenic trails, or simply soaking up the sun on a quiet beach, there's something for everyone on this enchanting island.

Real estate opportunities on Sugarloaf Key range from cozy waterfront cottages to luxurious estates, all designed to take full advantage of the stunning surroundings. With its unique combination of natural beauty and community spirit, Sugarloaf Key is not just a place to live; it’s a lifestyle. Discover your piece of paradise today and experience the magic of island living in Sugarloaf Key, Florida!

Newest Listings in Sugarloaf Key

$999,000
621067 MLS
Active Permit! Start building today! Save years of planning and permitting with this exceptional 21,600 sq. ft. waterfront parcel in sought-after Sugarloaf Shores. Situated on a wide canal with ocean-side access, this property includes transferable approvals for a single family home with a 100' dock and a 15,000-lb boat lift, along with engineered plans for a custom pool offering the ultimate head start on your Florida Keys dream home. Sugarloaf Shores is renowned for its crystal clear wide canals, mangrove lined paddle board and kayak trails, quiet residential streets, and estate-sized lots. Full architectural plans, engineering reports, and permit documentation are available upon request.

16770 Cypress Rd, Sugarloaf
$750,000
3 Beds ⋅ 2 Baths ⋅ 620938 MLS
Great opportunity to have your home in a charming neighborhood on Sugarloaf key, MM 19.5. Enjoy your 3-bedroom 2-bath single family home on a large 15000 sq ft lot with screened front porch and open patio in the backyard. This large yard has plenty of room for a pool, Boats, RV, Trailers and your toys! Home is located down the street from Sugarloaf School, 20 miles to Key West and 27 miles to Marathon. Home has been updated with custom kitchen cabinets, updated bathrooms, has central air, stainless steel appliances. Loan is assumable with 2.75% rate with qualification. Easy to show.

19421 Canal Dr, Sugarloaf
$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
$1,155,000
3 Beds ⋅ 2 Baths ⋅ 620753 MLS
Live on the water on one of the largest lots in Sugarloaf Shores, fronting a 70 ft wide crystal clear swimming canal with easy ocean access. Recent upgrades make this home truly turnkey, including a new seawall, a new boat lift 15,000 lbs), and a newer roof. The big ticket items are already done for you. The grounds are the professionally landscaped with mature trees, fruit trees, a custom rock wall, and plenty of space for RVs, boat trailers, or a pool. For boaters and fishermen you'll find a new dock with a covered fish cleaning station with lights and water, and an ice machine. The elevated home itself is fully renovated and fully furnished with a fresh coastal interior. It features Italian porcelain floors, a granite chef's kitchen, and a standout outdoor kitchen, making it a comfortable retreat after a day on the water.

17183 W Green Turtle Ln, 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
$3,750,000
4 Beds ⋅ 4 Baths ⋅ 619842 MLS
Morning Glory - The Dolphin House is one of those rare oceanfront sanctuaries where time softens, stress fades, and every sunrise feels like it was created just for you. Welcome to Morning Glory - The Dolphin House. There are homes you visit... and there are homes you feel the moment you arrive. Perfectly positioned on an oversized direct oceanfront lot, this extraordinary 4-bedroom, 3.5-bathroom residence with 2,478 square feet invites you into a lifestyle many dream about--but few ever experience. As you step inside, you are greeted by tasteful coastal elegance, natural light, and sweeping blue-water views that instantly quiet the mind. Every room feels intentional, warm, and beautifully curated. The décor blends sophistication with comfort, creating a space where luxury feels effortless. Imagine waking each morning in your private suite as the first golden light rises over the Atlantic. Open your eyes to endless turquoise water, soft breezes, and the promise of another perfect day. Walk onto the expansive veranda with your morning coffee, where the sunrise slowly paints the sky. In the evening, the moonrise becomes your private show--silver light dancing across the water while the world grows still. Outside, the experience becomes unforgettable. Spend afternoons floating in the pool beneath swaying palms. Gather friends and family for waterfront dining as laughter mixes with the ocean breeze. Slip into the hammock with soft music and your favorite book. End the night beside the fire pit with a warm drink, toasted marshmallows, and stories under a sky full of stars. This is more than a beautiful home. It is where memories are created. Where families reconnect. Where success is celebrated. Where peace returns. For the buyer who has worked hard and now wants to truly live well, Morning Glory - The Dolphin House is not just a property. This is more than a beautiful oceanfront home. It is where memories are created. Where families reconnect. Where success is celebrated. Where peace returns. For the buyer who has worked hard and is ready to live well, truly, Morning Glory - The Dolphin House is not just a property. It is a reward. It is a retreat. It is a lifestyle. It is your chance to own a piece of oceanfront paradise.

17387 E Dolphin St, Sugarloaf
$799,000
3 Beds ⋅ 2 Baths ⋅ 619536 MLS
Opportunities like this are hard to find in the Lower Keys--this fully renovated 3-bedroom, 2-bath home sits on a generous half-acre lot in the highly desirable Sugarloaf Key area, offering space, privacy, and modern upgrades throughout. Designed for easy coastal living, the home features durable Hardie board siding, a long-lasting metal roof, tile flooring throughout, and an energy-efficient tankless water heater. Inside, you'll find a bright, open layout that flows effortlessly to an expansive screened porch--perfect for relaxing or entertaining. Step outside to a 24' x 24' sun deck overlooking the oversized yard, where there's ample room to add a pool, store your toys, utilize the existing RV hookup, or enjoy fresh mangos right off the trees. The ground level provides covered parking for two vehicles and an abundance of space for additional uncovered parking. Ideally located near multiple boat ramps, this property is a dream for boating and fishing enthusiasts. You'll also be just minutes from the natural beauty of the Upper Sugarloaf Nature Preserve, the local Sugarloaf School, and a variety of popular dining spots. Whether you're searching for a full-time residence, vacation home, or investment property in the Florida Keys, this move-in-ready home checks all the boxes.

937 Loggerhead Ln, Sugarloaf
$699,000
619430 MLS
Build Your Dream Home in Sugarloaf Shores! Discover the rare opportunity to develop your very own piece of paradise in the exclusive Sugarloaf Shores! This 8,165 sq. ft. waterfront lot is high, dry, and cleared, offering a perfect blank slate for your dream home in the Florida Keys. With a full 70' concrete seawall, this property is a boater's paradise, providing direct access to both the Atlantic Ocean and the Gulf of Mexico. All permits for construction have been awarded and are in hand, streamlining your path to creating the perfect coastal retreat. Conveniently located just 15 minutes north of Key West and 15 minutes south of Big Pine Key, this property offers the ideal balance of serene living and easy access to vibrant island life. Don't miss your chance to design and build your custom home in one of the most sought-after waterfront communities in the Keys. Imagine enjoying breathtaking water views and endless boating adventures right from your backyard! *Seller is a licensed FL Realtor

17220 Angelfish Ln, 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
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