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Sugarloaf Key Waterfront Homes For Sale on the Ocean Side of the Island. Oceanfront Homes

Total Listings 28
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$2,250,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,750 SqFt Days Listed: 133
-9.96% ($249,000) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: DavitsConcrete

Tropical Paradise and Boaters Dream!Welcome to this custom-built 3-bedroom, 2-bathroom home in the prestigious Sugarloaf Shores, just 15 minutes from Key West and a short boat ride to the most stunning sandbars in the Florida Keys. Nestled on an expansive 15,000+ sq. ft. corner lot, this all-concrete home offers over 1,700 sq. ft. of beautifully designed living space. The property is fully fenced and surrounded by lush tropical landscaping, providing a private retreat with waterfront views. Step inside to an open-concept floor plan that seamlessly blends elegance and functionality, perfect for entertaining. The kitchen is a chefs dream, featuring custom cabinetry, granite countertops, and stainless-steel appliances. The spacious master suite includes private access to the large balcony overlooking the canal, a luxurious ensuite with a stunning walk-in shower, and dual walk-in closets. On the ground level, youll find a 3-car garage, a separate storage room, and a paved driveway. The outdoor space is an entertainers delight with a sparkling pool, a whole-home generator for peace of mind, and direct access to a wide canal, ideal for boating enthusiasts. With its impeccable design, premium features, and unbeatable location, this Florida Keys gem is truly a must-see. Dont miss your chance to own this slice of paradise!

$2,297,000
Sugarloaf Key
Sugarloaf Beach   - MM: 17.00
2 Bed, 2 Baths, 1,202 SqFt Days Listed: 105
-2.21% ($52,000) 1 Price Change : Last Change 26 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Come explore 17270 Old State Road 4A, a rare gem nestled on almost 3 expansive acres of prime oceanfront land in Sugarloaf Key. This stunning property offers sweeping, unobstructed open ocean views, making it a perfect escape or retreat for those who appreciate natures beauty and tranquility.Featuring large wrap-around decks on both floors, this home is designed to seamlessly blend indoor and outdoor living. Take in the breathtaking vistas, enjoy sunrise and sunset views, or entertain guests in style, all from the comfort of your expansive decks. For a truly panoramic experience, head up to the crows nest viewing area on the roof, where you can enjoy 360-degree views of the surrounding waters and lush landscapes.Enjoy ultimate privacy with a long, 500-foot driveway that leads you to your secluded paradise, away from the bustle of everyday life. Surrounded by natural beauty, this property offers a sense of peace and serenity thats hard to find anywhere else in the Florida Keys.With plenty of room to grow, this property offers endless possibilities. The large cleared lot provides ample space to expand the current footprint of the home, whether by extending out onto the decks or adding additional structures on the land. Whether youre looking to build your dream home or create a larger, more elaborate estate, the options are limitless.This is truly a one-of-a-kind opportunity to own a piece of ocean front paradise in the Florida Keys. Dont miss your chance to own a slice of heaven at 17270 Old State Road 4A, Sugarloaf Key--where luxury meets nature in perfect harmony.

$2,375,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
5 Bed, 5 Baths, 2,772 SqFt Days Listed: 100
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits120ft.Concrete

Beautiful open water 5 bedroom 4 bathroom South Point Sugarloaf Key dream home. Very well laid out for an array of guests or family to gather with a split floor plan including a large master suite with a wall of windows to wake up each morning to the turquoise water of the Florida Keys. Enjoy wall to wall stunning open water views, there are so many areas to bask in this waterfront delight. The 12,500 sq. ft. lot offers an endless array of possibilities for outdoor play or the addition of a pool. The 120 ft. concrete seawall with davits is a boaters delight for great and easy access to world class fishing, diving or lounging at the famous sandbars. The elevated home allows for the entire lower level to be another outdoor lounge and entertainment area. There are two large storage areas to store all your toys and gear as well as plenty of room for parking.Enjoy the magic of peaceful waterfront living in one of the Lower Keys most coveted neighborhoods and also just a 15 minute drive from Key West. Schedule your private showing today, in person or with a live video showing.

$2,495,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,192 SqFt Days Listed: 7
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 40ft.

Welcome to this stunning 3-bedroom, 2-bathroom home perfectly situated on nearly half an acre, offering serene water views and direct canal access. Ideal for boaters and outdoor enthusiasts, the property features a concrete dock--your gateway to waterfront adventures.Step inside to an open floorplan designed for both comfort and entertaining. The heart of the home is a beautifully updated kitchen, complete with modern finishes, ample counter space, and a layout that flows seamlessly into the living and dining areas.Large windows invite natural light and showcase the scenic surroundings, creating a relaxing and inviting atmosphere throughout. The spacious bedrooms offer plenty of room for family or guests, while the bathrooms are tastefully appointed for everyday luxury.Outside, Your brick paved driveway leads you to your elevated home. With space underneath to cook, entertain or just lounge in the shade. NEW POOL is surrounded by your updated and LUSH landscaping creating privacy for your daily dips or after a day on the water! Enjoy the best of Florida Keys living with access to community parks and bike paths, perfect for morning strolls or weekend rides. Whether youre sipping coffee on the patio or setting off from your dock for a day on the water, this property blends comfort, lifestyle, and location in one exceptional package.

$2,499,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,288 SqFt Days Listed: 19
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

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 homes 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.

$3,499,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,472 SqFt Days Listed: 103
-9.70% ($375,900) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Welcome to the most exceptional home and premier lot currently available in the prestigious Sugarloaf Shores neighborhood. This property is a masterpiece of luxury, craftsmanship, and natural beauty, offering a lifestyle that truly must be experienced in person to be fully appreciated.Situated on an expansive 13,000+ square foot private point lot, this home boasts over 230 feet of crystal-clear waterfront, providing unmatched panoramic open-water views. Facing west, the property delivers daily breathtaking sunsets over gin-clear turquoise waters--a sight that no other lot can compare to.Completely remodeled with no detail overlooked, the home features an open-concept design with brand-new stainless steel appliances, quartz countertops, and elegant warm tile flooring throughout. The spacious master suite opens to a covered porch, while the living rooms fully pocketing sliding doors blur the line between indoors and outdoors. Over 550 square feet of covered porches create an ideal space to relax and take in the stunning surroundings.The exterior is equally impressive. A brand-new custom concrete pool, both heated and chilled, includes a built-in spa, while the yard is entirely landscaped with turf and river stone accents for easy maintenance. Boaters will love the 15,000 lb boat lift, kayak pier, and the newly thatched tiki hut with a fan for shaded relaxation.Practicality meets peace of mind with impact hurricane windows and doors paired with roll-down or accordion shutters, a new roof, and spray foam attic insulation. The lower level features over 1,100 square feet of enclosed space, including a workshop and extra-height garage door for storing small vessels on trailers.Located just 20 minutes from Key West Airport, world-class restaurants, and shopping. With its one-of-a-kind views and unmatched design, privacy, and location, this property stands as one of the finest offerings in the Keys today.

$3,795,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 3,086 SqFt Days Listed: 251
-15.57% ($700,000) 3 Price Changes : Last Change 17 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Exquisite Open Water Estate on Prestigious Southpoint, Sugarloaf Key! Experience unparalleled luxury at this stunning solid concrete open water property, located just 20 minutes from the magic of Key West and Key West Airport. Situated on prestigious Southpoint, Sugarloaf Key, this magnificent estate offers breathtaking open water views and a lifestyle of elegance and comfort.Spanning 3,086 square feet of refined living space, this home features 3 bedrooms, 2 bathrooms, plus a versatile office/den and a large laundry room. The expansive 19,300 square foot lot is a tropical paradise, beautifully landscaped with fruit trees, an orchid house, landscape lighting, and irrigation from cisterns.Step inside to discover poured concrete floors that exude modern sophistication. The chefs kitchen is a culinary dream, equipped with Miele appliances and a Sub-Zero refrigerator. Entertain with ease in the separate bar area and enormous living space. The property also boasts a ducted vacuum system and a commercial-grade metal roof for added convenience and durability. Outdoor living reaches new heights with a stunning new pool, featuring a long ledge perfect for relaxing with cocktails. The large tiki hut serves as an outdoor lounge, complimented by a separate bar area under the house adjacent to the pool. The dock and boat lift provide direct access to the open water, making this home a boaters dream. Enjoy the convenience of an elevator, granting access from the garage and ground level to all floors. The rooftop deck offers 360-degree views, including vistas of the open ocean, perfect for sunset soirees or stargazing nights. This estate is designed for the discerning luxury buyer, offering the perfect blend of sophistication, comfort, and tropical charm. Dont miss the opportunity to own a piece of paradise on Sugarloaf Key! Low Insurances. Call for your private showing today! Video tour https://tinyurl.com/16705Tam

$4,950,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
4 Bed, 4 Baths, 2,907 SqFt Days Listed: 167
-9.90% ($544,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift100ft.

Huge Price Improvement! Welcome to your waterfront paradise! This solid concrete, newly built 4-bedroom, 4.5-bath home offers unparalleled luxury finishes and an open floor plan designed for modern coastal living. The chefs kitchen is a culinary dream, featuring state-of-the-art appliances and an open layout flowing seamlessly into the spacious living and dining areas. Expansive balconies offer beautiful views and include a summer kitchen for outdoor dining and entertaining. The master suite is a private oasis on its own floor, complete with a sun deck, walk-in closets, and a large balcony perfect for relaxation.With a 100-foot seawall, a 25,000 lb boat lift, and a floating dock for jet skis, this property is an ideal base for water enthusiasts. Relax in the heated pool or enjoy the thoughtfully designed outdoor spaces for cooking and lounging. Just 20 minutes from Key West and 15 minutes from Marathon, this luxurious property combines convenience and tranquility. Furniture, boat, and jet ski are available as optional add-ons, making this turnkey retreat an exceptional opportunity to own your piece of paradise!

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 04-22-2025.
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