Divider
Content Divider
Total Listings 31
Order By:

$1,240,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,528 SqFt Days Listed: 285
-8.15% ($110,000) 3 Price Changes : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Cut/Natural

This lovely, beautifully landscaped waterfront home, is located on a quiet street in the very desirable neighborhood of Sugarloaf Key. Move-in ready and equipped for easy Keys living. This CB constructed home features granite countertops , stainless appliances, impact windows, a large screened in porch and storage-up and down. All insurances under 5K and is assumable. With 3 bedrooms, one with a murphy bed and 2 baths, this low maintenance home allows you to enjoy all the Keys has to offer. Located on a private peaceful canal, you are just minutes from the back country and ocean waters. Dock Permit is in hand. Close to Sugarloaf schools and just minutes from Key West.

$1,199,000
Sugarloaf Key
Orchid Park Subdivision   - MM: 17.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 10
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 80ft.Concrete

Located in the highly desirable Sugarloaf Shores neighborhood this 3 Bedroom, 2 Bath canal front home features an open concept floorplan encased in natural light and glass windows looking out to views of privately owned conservation land across the canal. Opening to the Living Room the Kitchen is well equipped with quartz countertops, stainless steel Whirlpool appliances, shaker cabinets and center island for entertaining. The Primary Suite enjoys a large walk-in closet and luxury bath with glass shower, soaking tub, double sinks and quartz countertops. Morning coffee is enjoyed on the wrap-around Porch with pretty canal and preserve views. Plenty of room for all of your toys at the full length 80 concrete dock offering easy ocean access and underwater lighting. The beautifully landscaped lot provides for ultimate privacy and seclusion and is adorned with lots of mature plants and trees including mahogany, buttonwood, pear and a variety of palms. Built in 2018 to the new 180 mpg wind codes the home is storm ready with hurricane impact doors and windows, metal roof and whole house generator. A full irrigation system, landscape lighting and four 125-gal propane tanks complete his wonderful home.

$1,149,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
2 Bed, 2 Baths, 1,875 SqFt Days Listed: 43
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Nestled along a serene boating canal, this exceptional 2-bedroom, 2-bathroom home is a true masterpiece, crafted entirely from luxurious teak wood. With its timeless beauty and durable design, this home perfectly complements its natural surroundings, offering a tranquil retreat for water lovers.Step inside to find soaring cathedral ceilings that elevate the spacious living areas, flooding the space with natural light and creating a warm, open atmosphere. The heart of the home includes a beautifully designed living area that flows seamlessly into the screened-in back porch, ideal for enjoying year-round outdoor living.Enjoy a unique, carved swimming area, perfect for cooling off or simply relaxing by the water. With direct access to the canal, this home is perfect for boating enthusiasts, offering convenience and charm right at your doorstep.Additional perks include ample parking and abundant storage space, making this home as practical as it is stunning.Dont miss your chance to own this one-of-a-kind teak beauty. Schedule your showing today and experience waterfront living at its finest!

$1,129,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,859 SqFt Days Listed: 18
-0.88% ($10,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift55ft.

Located on the tranquil side of Sugarloaf Key, this stunning 1,859 square ft home offers the ultimate boating access -- no bridges to navigate and direct access to the pristine waters of the Florida Keys. The 55-foot dock with a 10K boat lift ensures seamless access to world-class fishing and diving, right from your own backyard. Perfect for water lovers and outdoor enthusiasts, this home is an entertainers dream. Inside, soaring ceilings and rich wood floors exude warmth and charm, while a cozy wood-burning fireplace adds an element of rustic elegance. Expansive sliding glass doors open to a sprawling veranda that captures cool ocean breezes and enhances the flow between indoor and outdoor living.The gourmet kitchen boasts custom wood cabinetry, high-end stainless steel appliances, and plenty of prep space, making it perfect for preparing meals for family and friends. The open layout allows easy flow from kitchen to dining to living spaces, creating the perfect environment for entertaining.Three generously-sized bedrooms provide comfort, privacy, and ample storage space. A dedicated laundry room offers convenience, while the fully permitted two-car garage underneath provides secure parking, with extra space for trailers, boats, and additional vehicles.Step outside to the screened-in patio, featuring a heated jetted swim spa -- the perfect place to unwind after a day of fishing, diving, or simply enjoying the water. Surrounded by lush, tropical landscaping, this home offers unmatched access to open water, giving you the freedom to explore the Keys from your doorstep.The roof was replaced in 2018 with durable, long-lasting metal, ensuring peace of mind and protection for years to come.With the added benefit of being located just minutes from local shops, restaurants, and attractions, this home provides an unmatched blend of relaxation, adventure, and convenience. Designed for those who want to live the ultimate Florida Keys lifestyle

$1,100,000
Sugarloaf Key
Vacation Harbor   - MM: 19.50
3 Bed, 3 Baths, 1,152 SqFt Days Listed: 14
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Step into your own private paradise! This beautifully maintained home offers 3 bedrooms, an office space, and 2 full bathrooms, making it the perfect retreat. Situated on a deep-water canal with 68 feet of dockage, youre just minutes away from the open Atlantic or the serene backcountry sandbars. Whether from the living room, bedrooms, or expansive screened porch, youll enjoy breathtaking views of the open water at every turn.The home has been thoughtfully upgraded both inside and out. The kitchen is a chefs dream with modern GE profile appliances and the luxury of gas cooking. The sleek quartz countertops and bamboo flooring throughout the home provide a modern yet inviting atmosphere. If youve been dreaming of a tranquil sanctuary to call home, look no further--this is the place where you can truly unwind and embrace the waterfront lifestyle.

$1,075,000
Sugarloaf Key
Orchid Park Subdivision   - MM: 17.00
3 Bed, 3 Baths, 1,248 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Welcome to 17245 Jamaica Lane, a waterfront 3-bedroom, 2-bathroom home in the desirable Sugarloaf Shores. This elevated residence offers 1,248 square feet of comfortable living space with beautiful canalfront views and direct canal access for boating and fishing enthusiasts. This home offers distinct living, dining, and kitchen areas, creating a natural flow. The kitchen includes granite countertops, modern appliances, and ample storage, providing a functional and stylish space for cooking and entertaining. The primary bedroom offers plenty of natural light with an en suite bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. Enjoy serene canal views from the rear balcony, perfect for relaxing or unwinding after a day on the water. With direct boating access, youre just minutes from world-class fishing, sandbars, and the best of the Lower Keys. The spacious lot offers room for a pool, allowing you to create your own private backyard oasis. On the ground level, youll find a garage and covered space--ideal for storage, a workshop, or a shaded outdoor lounge. Plus, off-street parking provides plenty of room for vehicles, a boat, or even an RV. Located in a quiet neighborhood, this home is perfect as a primary residence, weekend retreat, or vacation rental opportunity. Dont miss your chance to own a slice of paradise--schedule your private showing today!

$999,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
2 Bed, 2 Baths, 1,344 SqFt Days Listed: 7
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

Located in the heart of Sugarloaf Shores, this 1,344 sq ft, 2-Bedroom waterfront Pool home boasts a resort-style outdoor setting on a large corner lot. Hidden behind the luscious landscape is a sparkling pool adorned with lots of pavers and 2 well equipped Tikis providing plenty of shade and space to entertain friends. Enter into the spacious Great Room highlighted by soaring ceilings and many picture windows allowing an abundance of natural light and pretty views of the gardens. The open Kitchen features stainless steel appliances, beverage cooler, granite countertops, lots of wood cabinetry and center island for people to gather around. A large pantry/laundry room could easily be converted to a 2nd bath. Each Bedroom has ample closet space and private entry to the full Bathroom with the Primary Bedroom having direct access to the outdoor shower and water closet on the adjacent Porch. Located on the no bridge side of Sugarloaf Key with quick ocean access through Tarpon Creek. This elevated home offers plenty of covered parking and room for all your recreational vehicles and boat trailers. Offering a ton of privacy this property is unique and perfectly melds the outdoor and indoor spaces to provide the ultimate Florida Keys lifestyle.

$989,000
Sugarloaf Key
Indian Mound Estates   - MM: 19.50
2 Bed, 2 Baths, 1,160 SqFt Days Listed: 15
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Motivated seller! Bring all Reasonable offers. for this Oversized Double Lot with 2 bedrooms, 1.5 baths. A beautiful custom-designed CBS pool with a sandy beach. There is a private boat ramp and dock at the homeowners park at the end of the street. Located in the established Indian Mound Estates neighborhood, its just minutes from shops, restaurants, and within walking distance to schools. You can also bike ride in the nature wildlife reserve. Plenty of room for all your Toys!!! Conveniently close to Key West.

$874,000
Sugarloaf Key
Indian Mound Estates   - MM: 19.50
3 Bed, 3 Baths, 1,560 SqFt Days Listed: 50
-2.78% ($25,000) 1 Price Change : Last Change 4 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp,None

ASSUMABLE VA LOAN for qualified Buyer with an approximate remaining balance of $785,000 at 3.75%! Welcome to your dream conch style house, a true gem designed for those who appreciate character and charm. Nestled on a fully fenced generous 10,000 square-foot lot surrounded by protected land, this property offers a remarkable level of privacy and tranquility, all without the burden of extra costs. This distinctive eyebrow house boasts three spacious bedrooms located on the upper level, ensuring a perfect split floor plan that enhances both comfort and functionality. The main level features a cozy living area, a bright dining space, and an expansive Florida room, offering versatility for use as an additional bedroom, a home office, or a play area for kids. Natural light pours in through the wraparound windows at the back of the house, creating a warm and inviting atmosphere. Outside, the tropical yard is a private oasis, featuring an above-ground pool, swing set, and lush, mature landscaping dotted with flourishing fruit trees. Located in the sought-out family neighborhood of Indian Mounds on Sugarloaf Key where they have holiday traditions year-round! There is a community boat ramp approximately a half a mile from the house with key access for you to launch your boat, or other water toys for a day of fun in the sun! With its many unique features and undeniable charm, this home is a must-see. Come experience it for yourself and envision the possibilities that await! Tour the tropical yard with endless fruit trees including a mango tree (which produced 100 mangos last year), banana tree, orange tree, fig tree, avocado, papaya and pineapple! Newer appliances; metal roof along with impact windows and doors equals affordable insurance! Approximately 15 miles from Key West and 30 miles from Marathon.

$659,000
Sugarloaf Key
Indian Mound Estates   - MM: 19.50
2 Bed, 2 Baths, 1,129 SqFt Days Listed: 87
-5.72% ($40,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled in a quiet and charming neighborhood on Sugarloaf Key, this beautifully remodeled 2-bedroom, 2-bathroom home offers a perfect blend of modern updates and coastal charm. With plenty of natural light throughout and crown molding accenting every room, this home feels both elegant and welcoming. The kitchen features newer, stainless steel appliances and stylish finishes, making it ideal for both everyday meals and entertaining. The spacious primary bedroom boasts a large, updated en suite bathroom. The second bedroom and additional bath are equally well-appointed, making this home perfect for both family living and hosting guests. Located just down the street from a private neighborhood boat ramp that can only be accessed with a resident key, this home offers easy access to the crystal-clear waters of the Florida Keys. The large yard provides plenty of room for trailer storage, so you can easily store your boat, RV, or other toys. Theres also ample space to add a pool, creating your oasis in the heart of the Keys. Built with durability in mind, the home features impact windows, a metal roof, insulation in the attic, and hurricane shutters for added peace of mind and protection from the elements. This combination of energy efficiency and storm preparedness ensures that you can enjoy both comfort and security in your new home. Whether youre relaxing in the cozy interior or spending time outside, this home offers the perfect spot to unwind and enjoy the laid-back Keys lifestyle. Dont miss the opportunity to own this turnkey gem in a prime location!

$630,000
Sugarloaf Key
Indian Mound Estates   - MM: 19.50
2 Bed, 2 Baths, 989 SqFt Days Listed: 30
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to 19557 Mayan St, a solid CBS 2-bedroom, 2-bath home Nestled in the sought-after Indian Mounds neighborhood on Sugarloaf Key. The perfect Florida Keys bungalow, this home has been completely updated and features an open floor plan, brand new appliances + quartz countertops, renovated bathrooms, and new floors throughout. The property has a separate room (currently used for utility/ storage) and features 473 sf of screened in porches offering true indoor outdoor living. This home sits on a 5,000sf lot and in addition to the PRIVATE boat ramp, there is a community only beach for residents to enjoy as well. Set in a quiet, welcoming neighborhood, this home is also just a short walk to the Key Deer Preserve, Sugarloaf School, and a 5 minute drive to the famous Babys Coffee shop. For boaters, the location offers quick access to the Gulfside sandbars in just 15 minutes.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 03-14-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA