Sugarloaf Key FL Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
1,344
Status:
Active
MLS#:
619901
Type:
Single Family
Subdivision:
Orchid Park Sub (17.0)
Lot size:
0.18 Acres
Year built:
2000
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,409
Status:
Active
MLS#:
B26028168
Type:
Single Family
Subdivision:
SUGARLOAF SHORES PLAT #2 SEC C
Lot size:
0.36 Acres
Year built:
2021
Courtesy: Coldwell Banker Schmitt RE Co 305-743-5181
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ADDITIONAL INFORMATION

Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about. Wake up to stunning sunrises, relax by the pool beneath swaying palms, enjoy waterfront dining with guests and friends, or unwind by the fire pit under the stars. Every space was designed to feel warm, inviting, and effortlessly luxurious. More than a home, this is a private sanctuary where memories are made and life slows down.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,548
Status:
Active
MLS#:
619875
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.3 Acres
Year built:
1981
Courtesy: Berkshire Hathaway HomeServices Knight & Gardner Realty 305-294-5155
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,398
Status:
Active
MLS#:
619637
Type:
Single Family
Subdivision:
Vacation Harbor (19.5)
Lot size:
0.14 Acres
Year built:
1987
Courtesy: Coastal Collection Real Estate Inc. 305-731-7910
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ADDITIONAL INFORMATION

Recently updated canal-front home in highly desirable Upper Sugarloaf Key with direct boating access to the world famous Florida Keys back-country and Gulf of America. Located at 885 Hawksbill Lane, this waterfront property sits on a 6,120 sq ft lot and features a concrete seawall with boat davits, pavers and a heated swimming pool and spa completed in 2022. Enjoy canal and mangrove views plus easy access for fishing, kayaking, and boating right from your backyard. Inside, the home offers an open-concept living area with soaring 20-foot cathedral ceilings and abundant natural light. The updated kitchen includes Samsung stainless steel appliances, marble countertops, and a breakfast bar, creating a great space for cooking and entertaining. Glass sliders open to a spacious balcony, ideal for sunrise views, outdoor dining, and relaxing by the water. The flexible floor plan includes a large downstairs guest bedroom, an additional upstairs guest bedroom and a generous master suite with water views. Ample parking, a garage, and dedicated space for an RV or boat trailer provide the storage and convenience that Florida Keys boaters are looking for. This move-in-ready canal-front home is located in an upscale coastal community just about 20 minutes from downtown Key West, offering the perfect blend of privacy, waterfront lifestyle, and easy access to restaurants, shopping, and nightlife.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,624
Status:
Active
MLS#:
619598
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.27 Acres
Year built:
1979
Courtesy: Brenda Donnelly Real Estate LLC 305-304-1116
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ADDITIONAL INFORMATION

A quiet escape with million-dollar views. Situated on an expansive lot of over a quarter-acre, this three-bedroom, two-bathroom home is nestled within the sought-after shores of Sugarloaf Key--tucked away from the highway and just steps from scenic walking and bike paths. The interiors offer a crisp, modern take on coastal comfort, sold fully furnished with a curated collection of new decor and linens. The heart of the home is a chef's kitchen anchored by professional-grade THOR appliances. Built for lasting resilience, the exterior boasts high-durability siding and a metal roof, complemented by impact-rated windows and doors throughout for total peace of mind. An expansive wrap-around porch with low-maintenance composite decking encircles the home, providing the perfect vantage point to enjoy constant island breezes and panoramic open-water views. Secured by a fenced perimeter and private gated entrance, the grounds serve as a premier nautical enclave. A concrete dock and a rare, on-site boat ramp offer effortless access to world-class fishing and the Keys' signature turquoise waters. Functional details include covered parking and a generous downstairs storage area for dive gear and island essentials. This is the ultimate waterfront retreat--combining the polish of new construction with exceptional privacy, without the wait.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,488
Status:
Active
MLS#:
619597
Type:
Single Family
Subdivision:
Orchid Park Sub (17.0)
Lot size:
0.18 Acres
Year built:
2013
Courtesy: Homecoin.com 888-400-2513
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ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
984
Status:
Active
MLS#:
619536
Type:
Single Family
Subdivision:
Vacation Harbor (19.5)
Lot size:
0.5 Acres
Year built:
1994
Courtesy: Buy The Keys 305-916-9020
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,288
Status:
Active
MLS#:
619431
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.38 Acres
Year built:
2025
Courtesy: Truman & Co. (KW) 305-292-2244
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ADDITIONAL INFORMATION

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,522
Status:
Active
MLS#:
619394
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.28 Acres
Year built:
1988
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
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ADDITIONAL INFORMATION

This beautifully remodeled waterfront bungalow is nestled in the heart of Sugarloaf Shores ,one of the Lower Florida Keys' most desirable boating communities. Set on an expansive 12,500 sq ft lot surrounded by lush tropical landscaping, this elevated two-story home offers the perfect blend of privacy, comfort, and island charm. With 3 Bedrooms plus a Loft and 2 Bathrooms, the layout is thoughtfully designed to accommodate both entertaining and relaxation. The main living level features two Guest Bedrooms and a full Bath, along with an inviting open-concept living and dining area filled with natural light. The updated kitchen is a standout, complete with dining bar, stainless steel appliances and a gas rang which is ideal for preparing fresh local catch after a day on the water. Upstairs, the private Primary Suite and Loft create a peaceful retreat, offering separation and elevated views of the surrounding tropical setting. Outdoor living is where this property truly shines. Multiple Porches and a screened Lanai provide serene spaces to enjoy balmy breezes, while the expansive backyard leads to your dock along a clear, turquoise 80' wide canal with quick access to open water. Whether you're boating, fishing, paddleboarding, or kayaking through nearby mangrove creeks, adventure is always just moments away. After a day in the sun, relax in the outdoor hot tub and take in the tranquil surroundings. Additional features include bamboo flooring in the Bedrooms and a durable metal roof. Located just 15 minutes from Key West, Sugarloaf Shores offers a rare combination of peaceful island living with convenient access to dining, entertainment, and world-class recreation. Whether you're searching for a vacation home or a full-time waterfront residence, this property captures the essence of the Florida Keys lifestyle.

Beds:
2
Baths:
2.00
Sq.Ft.:
832
Status:
Active
MLS#:
619336
Type:
Single Family
Subdivision:
Sugarloaf Acres (19.5)
Lot size:
4.03 Acres
Year built:
1987
Courtesy: Bluescape Real Estate 305-203-2537
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,288
Status:
Active
MLS#:
619254
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.56 Acres
Year built:
2025
Courtesy: Truman & Co. (KW) 305-292-2244
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ADDITIONAL INFORMATION

A rare double-parcel waterfront opportunity in Lower Sugarloaf Key - offering a newly constructed home plus an adjacent buildable lot, creating the ultimate private boating compound. The newly built 3BD/2.5BA residence with an office/den & laundry/utility room spans 2,288sf on a 16,445sf lot and is thoughtfully designed with an open-concept layout, abundant natural light, and sweeping water views throughout. The primary suite features a spa-inspired bath, while outdoor living is elevated with an expansive balcony, private pool, tiki hut, custom landscaping, and a concrete seawall providing direct boating access (18' x 24'). The elevated construction offers a spacious carport and generous covered area, ideal for parking, storage, or entertaining. Included in the offering is the adjacent 8,165sf cleared waterfront lot, complete with a 70' concrete seawall and active building permits, perfect for a guest residence, additional structure, or expanded outdoor living space. This parcel also allows ample room for trailers, RV parking, or enhanced privacy through additional landscaping. Situated on a deepwater canal with direct access to both the Atlantic Ocean and Gulf of Mexico, this property is a boater's dream offering immediate access to world-class fishing, sandbars, and reef snorkeling, with capacity for a large vessel. Located just minutes from Key West, this is a rare opportunity to own a turn-key waterfront home with expansion potential in one of the Lower Keys' most desirable boating communities. *Seller is a licensed Florida Realtor.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,225
Status:
Active
MLS#:
619159
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.49 Acres
Year built:
1976
Courtesy: Coldwell Banker Schmitt Real Estate Co. (KW) 305-296-7727
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ADDITIONAL INFORMATION

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**

Beds:
3
Baths:
2.00
Sq.Ft.:
2,224
Status:
Active
MLS#:
619134
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.29 Acres
Year built:
2001
Courtesy: Suzanne Moore Real Estate 305-797-0699
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ADDITIONAL INFORMATION

Welcome to your private waterfront retreat in the highly sought-after Southpoint neighborhood of Sugarloaf Key - where space, privacy and effortless access to the open water redefine the Lower Keys Lifestyle. Positioned along a crystal clear canal just moments from the Bay, this elevated residence offers over 2200 sq.ft of thoughtfully designed living space, featuring three spacious bedrooms and two beautifully renovated bathrooms. Clean lines, natural light and an easy indoor/outdoor flow create that relaxed atmosphere that you expect in a Modern Florida Keys Home. At the heart of the Home, the gourmet kitchen is designed for both everyday living and entertaining, complete with premium finishes, abundant cabinetry, a walk-in pantry and an adjacent oversized laundry room for added convenience. Step outside to experience what truly sets this property apart from its competition. Situated on a generous 12,500 Sq Ft lot, the grounds have been recently meticulously landscaped to create a magnificent garden, with stunning palms and tropical foliage at every turn. The rear elevated deck is the ideal spot for an evening cocktail while the pool offers a refreshing escape after a day on the water. For boating and fishing enthusiasts, the private dock and boat lift provide immediate access to the open water, placing world class fishing, snorkeling and island hopping just minutes from your backyard. The ground level is designed for relaxed island living and entertaining featuring a covered outdoor living area with grill, sink, icemaker and refrigerator. Brick Paver walkways, easy to maintain artificial turf and manicured landscaping. Additional features include covered parking for multiple vehicles, boat trailer storage and a dedicated workshop for tools, gear and all your water toys. Located in one of the Lower Keys' most desirable neighborhoods, this stunning home delivers space & privacy that is increasingly hard to find.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,170
Status:
Active
MLS#:
618874
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.36 Acres
Year built:
2000
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,968
Status:
Active
MLS#:
618853
Type:
Single Family
Subdivision:
Sugarloaf Acres (19.5)
Lot size:
1.01 Acres
Year built:
1978
Courtesy: Expert Realty LLC (HQ) 305-587-7330
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,812
Status:
Active
MLS#:
618746
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.29 Acres
Year built:
1978
Courtesy: The Agency Florida Keys 305-916-1105
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ADDITIONAL INFORMATION

OPEN WATER RESORT STYLE CONCRETE POOL home on sought after Southpoint, Sugarloaf Shores. This exceptional 4-bedroom, 3-bath concrete waterfront residence captures breathtaking open water views from nearly every room and delivers the ultimate Florida Keys lifestyle. Positioned on a generous, beautifully landscaped lot with mature palms and established tropical greenery, the property welcomes you with a paved circular driveway, garage, expansive storage area, and pristine curb appeal. Inside, soaring cathedral ceilings elevate the open-concept living and dining area, where walls of glass frame endless turquoise water views and natural light pours in. The thoughtfully designed floor plan offers flexibility for luxury living and hosting. The second level features a spacious guest suite ideal as an alternate primary, 2 guest bedrooms, while the entire third level is dedicated to an enormous primary retreat. This private sanctuary includes a separate sitting area, panoramic open water vistas, and a stunning spa-inspired bathroom with soaking tub and refined finishes. Outdoor living is where this home truly shines. A screened-in porch overlooks the sparkling pool and unobstructed open water, creating the perfect setting for sunset cocktails or morning coffee. The expansive waterfront patio, low-maintenance turf, and fenced yard provide both privacy and ease of upkeep. Boaters will appreciate the concrete seawall and boat lift with immediate access to world-class fishing, diving, and offshore adventures. Concrete block construction, generous interior storage, dedicated laundry room, and meticulous landscaping complete this exceptional home. Rarely does a true open water pool home in this coveted Southpoint location combine views, elevation, lot size, and boating access so seamlessly. Private resort style home ideal for entertaing. Updated and move-in ready. Call to view this beautiful home in person.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,520
Status:
Active
MLS#:
618733
Type:
Single Family
Subdivision:
Orchid Park Sub (17.0)
Lot size:
0.18 Acres
Year built:
1987
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

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. Whether you're relaxing under the palms, tinkering in your workshop, or heading 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. Make it yours today!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,096
Status:
Active
MLS#:
618713
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.39 Acres
Year built:
1968
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,528
Status:
Active
MLS#:
618625
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.18 Acres
Year built:
2008
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
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ADDITIONAL INFORMATION

Completely reimagined and absolutely stunning, this beautifully remodeled home in Sugarloaf Shores showcases a full renovation, including a brand new dock. The beautiful 3 Bedroom 2 Bathroom home features commercial grade luxury vinyl floors, beautiful new finishes, custom cabinetry, new appliances, and fresh paint inside and out. Every detail was thoughtfully selected, creating a clean, modern coastal aesthetic that feels both stylish and inviting. Built for durability and peace of mind, the home features solid concrete construction, a metal roof, and impact windows, contributing to exceptionally low insurance costs. Recent updates include a newer AC system and water heater, making this a truly low maintenance property. The thoughtfully designed layout includes a beautiful primary suite with an en suite bathroom and walk in closet, along with two guest bedrooms that provide comfortable space for family or visitors. An open and spacious balcony extends the living area outdoors, offering the perfect place to grill, dine, or simply relax and enjoy the tropical surroundings. Positioned on a quiet street on Lower Sugarloaf Key the setting offers a lush tropical feel with brand new landscaping. With no neighbors across the canal and no possibility of future development, the property enjoys a uniquely peaceful backdrop. The spacious lot offers ample room for a pool, providing excellent potential for outdoor living. Enjoy excellent boating access with no bridges to the ocean. Located in the highly desirable Sugarloaf Shores neighborhood, just 20 minutes from Key West, this home offers the perfect combination of modern updates, solid construction, and the Lower Keys lifestyle.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,060
Status:
Active
MLS#:
618536
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.59 Acres
Year built:
1970
Courtesy: Expert Realty LLC (HQ) 305-587-7330
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ADDITIONAL INFORMATION

Experience the ultimate island lifestyle in this breathtaking waterfront residence located in the prestigious Sugarloaf Shores subdivision. Situated on a massive 25,482 sq. ft. lot, this property offers rare privacy with plenty of room to breathe. Built with solid CBS construction, this 5-bedroom, 4-bath home is designed to capture the beauty of its surroundings. The open living space and full-service kitchen flow seamlessly, creating a wonderful feeling throughout the home that is perfect for entertaining or relaxing. Step outside to your own private paradise. The grounds are impeccably maintained with mature, well-manicured landscaping that frames stunning open water and canal views. Wake up to spectacular sunrises and enjoy the best of waterfront living with an impressive 215 feet of canal frontage, including a 65-foot seawall. Unique to this property is a private sandy beach, providing perfect access for swimming, kayaking, and launching wave runners directly from your backyard. Active families will love the private basketball court, while the expansive outdoor space invites you to soak up the sun and the views. For boating enthusiasts, there's easy access to backcountry fishing, beaches, and the ocean. Although Sugarloaf is known for its peaceful neighborhoods, it is only minutes from the magic of Key West and all it offers, including fine dining, theater, museums, and of course, shopping. This is more than a home; it's a retreat offering space, seclusion, and premier water access. Don't miss this opportunity to own a slice of paradise.

Beds:
4
Baths:
4.00
Sq.Ft.:
1,744
Status:
Active
MLS#:
618532
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.27 Acres
Year built:
1997
Courtesy: Coldwell Banker Schmitt RE Co. 305-872-3050
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ADDITIONAL INFORMATION

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 (buyers choice), 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. All 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 awa

Beds:
4
Baths:
4.00
Sq.Ft.:
2,660
Status:
Active
MLS#:
618184
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.77 Acres
Year built:
1981
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
1,804
Status:
Active
MLS#:
618105
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.56 Acres
Year built:
1985
Courtesy: The Agency Florida Keys 305-916-1105
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ADDITIONAL INFORMATION

Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted 37,139 sqft lot point lot with A massive 362 FT OF WATERFRONTAGE on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. (24,662 sqft Upland & 12,477 submerged). These point lots are extremely limited and among the most sought-after properties on Sugarloaf, prized for their expansive water frontage and commanding views of sunrise, sunset, and moonrise. Set on a massive, fenced, and lushly landscaped lot, this extraordinary waterfront retreat enjoys no bridges to open water, making it ideal for boaters with T-tops and tuna towers. The open water side remains unobstructed, while the canal side features three boat lifts,a 10,000-lb lift, a 5,000-lb lift, and a 5,000-lb jet ski lift, thoughtfully positioned to preserve the spectacular open water views. The private sandy beach is perfect for launching paddleboards, kayaks, and water toys, while the pool creates a serene resort-style setting for relaxation and entertaining. The property is configured as a charming coastal compound, featuring a main residence with 2 bedrooms and 2 bathrooms, complemented by two separate studio cottages, each with its own bathroom, ideal for guests, extended family, or a private retreat feel. Nestled within a quiet, upscale waterfront neighborhood, Sugarloaf Shores is known for its pristine canals, biking and hiking trails, and relaxed island atmosphere, all while being just minutes to shops and restaurants and only 20 minutes from the magic of Key West. This is an incredible opportunity to own one of Sugarloaf Key's most exceptional and rare point lots where privacy, open water beauty, and effortless boating come together in perfect harmony.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,700
Status:
Active
MLS#:
618059
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.23 Acres
Year built:
2026
Courtesy: Expert Realty LLC (HQ) 305-587-7330
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ADDITIONAL INFORMATION

Modern luxury seamlessly blends with relaxed tropical living in this oversized, brand-new construction home located on Sugarloaf Key. This elevated three-story residence features 5 bedrooms and 5 bathrooms all en suite, offering approximately 3,700 square feet of thoughtfully designed living space on a 10,000-square-foot lot. Designed with both lifestyle and functionality in mind, the home showcases top-of-the-line Sub-Zero and Wolf appliances, a full Smart Home system, and the largest residential elevator permitted, providing effortless access between levels. An enclosed garage and expansive storage areas beneath the home offer ample space for vehicles, toys, and fishing gear. The outdoor living is equally impressive. A large private heated pool sits along the side of the home, surrounded by artificial turf, professional landscape lighting, and outdoor speakers, creating a serene tropical setting ideal for entertaining or unwinding in complete privacy. Boaters will appreciate the 100 feet of canal frontage with a 3-foot control depth, making this an ideal property for everything from offshore fishing adventures to relaxed sandbar cruising. Whether you're a serious angler or simply enjoy life on the water, this home delivers. Just 20 minutes from Key West, Sugarloaf offers the perfect balance of convenience and tranquility—close enough to enjoy the energy of downtown, yet far enough to experience true seclusion. This exceptional waterfront home is a rare opportunity and a must-see. Listing Broker Owned / Interest.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,272
Status:
Active
MLS#:
618014
Type:
Single Family
Subdivision:
Gulf Shores (19.5)
Lot size:
0.28 Acres
Year built:
1984
Courtesy: Island Life Realty Experts 305-766-0585
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ADDITIONAL INFORMATION

Escape to your own private paradise at 19881 Date Palm Drive in Sugarloaf Key! This beautifully updated single-family home sits on a fenced double lot and offers 100 feet of pristine canal frontage with a cut-in boat slip--perfect for boating enthusiasts with no neighbors across the canal! Step inside to find rich Brazilian hardwood floors, custom wood cabinetry, and sleek concrete countertops that bring warmth and modern character to the living space. A spacious legal lower enclosure (over 1,400 sq. ft.) adds versatility--ideal for storage, hobby space, or entertaining. Enjoy island living on your expansive deck with a wraparound catwalk, or take in the lush, tropical landscaping from your composite dock. The fully fenced lot also includes a detached shed, and there's ample room to add a pool or park your RV. Don't miss this rare canalfront gem in one of the Lower Keys' most desirable areas. Schedule your private showing today and make island life a reality!

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Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.




Sugarloaf Key Real Estate

Sugarloaf Key is located in Florida. Sugarloaf Key, Florida has a population of 3,304.

The median household income in Sugarloaf Key, Florida is $95,365. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Sugarloaf Key is 50.4 years.

Sugarloaf Key Weather

The average high temperature in July is 89.4 degrees, with an average low temperature in January of 63.4 degrees. The average rainfall is approximately 44.4 inches per year, with 0 inches of snow per year.

Sugarloaf Key Map

Sugarloaf Key Real Estate Market Conditions

  • Median sales price

    $1,329,500
    -3276800%
    change since last quarter
  • # Active listings

    49
    30-day change

Sugarloaf Key Schools and Demographics

Education near Sugarloaf Key, FL

City County
High School Graduates 96.84 92.07
College Degree - 2 year 7.68 7.93
College Degree - 4 year 41.72 35.69
Graduate Degree 10.7 9.88
Expenditures per Student 20,907 20,907
Students per Teacher 14.7 14.7

Elementary Schools near Sugarloaf Key, FL

Grades Students P/T Ratio ZIP
Gerald Adams Elementary School PK - 05 544 13.3 33040
Horace O'Bryant School PK - 08 1,059 14.3 33040
Key West Montessori Charter School KG - 08 149 16.6 33040
Monroe Virtual Instruction Program (District Provided) KG - 05 6 33040
Poinciana Elementary School PK - 05 663 15.1 33040
Sigsbee Charter School KG - 08 478 17.1 33040
Stanley Switlik Elementary School PK - 05 566 14.2 33050
Sugarloaf School PK - 08 526 15 33042
Treasure Village Montessori Charter School PK - 08 213 14.2 33036

Middle Schools near Sugarloaf Key, FL

Grades Students P/T Ratio ZIP
Glynn Archer Elementary School PK - 05 394 15.8 33040

High Schools near Sugarloaf Key, FL

Grades Students P/T Ratio ZIP
Key West Collegiate School 09 - 12 78 15.3 33040
Key West High School 09 - 12 1,193 16.8 33040

Ungraded Schools near Sugarloaf Key, FL

Grades Students P/T Ratio ZIP
* Keys Center 08 - 12 11 11 33040
Academic Connections for Excellence 06 - 12 11 33040
Adult/Vocational/Community Education AE - AE 0 33040
Marathon School 06 - 12 667 18.5 33050
Monroe Virtual Academy (Course Offerings) 06 - 12 0 33040
Monroe Virtual Franchise 06 - 12 4 33040
Monroe Virtual Instruction Program KG - 12 0 33040

Demographics near Sugarloaf Key, FL

City County
Neighborhood Type Small town
Population 3,304 82,244
Population Density 259 84
Median Age 50.4 48
People per Household 2.4 2.4
Median Household Income 95,365 73,153
Average Income per Capita 61,118 50,050

Real estate near Sugarloaf Key