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Winston Waterway Homes for Sale, Key Largo, Florida Keys

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Total Listings 4
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$1,250,000
Key Largo
Winston Waterway - MM: 102.00
3 Bed, 3 Baths, 2,075 SqFt Days Listed: 26
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift50ft.

Welcome to this ocean side canal front home that blends strength, style, and charm. This 3-bedroom, 3-bath concrete bunker with a concrete roof offers peace of mind and lasting quality, along with impact windows and doors. This home is all about function, durability, and waterfront living. The large kitchen boasts stainless steel appliances, ideal for preparing fresh catch or hosting friends. The living area features beautiful pecky cypress walls, wood beam ceilings and a cozy fireplace that creates warmth and character, while custom blinds throughout the home add a touch of sophistication. The spacious primary suite features cedar-lined closets and an updated bath, offering comfort and privacy with a split-bedroom layout that separates it from the guest rooms. Step outside to your waterside screened balcony to enjoy the views, have your morning coffee or evening cocktails. Downstairs, youll find a spacious storage and workshop area -- ideal for all your gear, tools, and hobbies -- along with plenty of parking for family, guests, and your boat trailer. The large backyard offers endless potential, with room for a pool, a cozy fire pit for stargazing nights, and a covered porch perfect for outdoor gatherings. Your new home is situated on a wide clean ocean side canal with a 14000 LB boat lift to enjoy the Keys waters. Located in a peaceful, sought-after neighborhood, this home is just minutes from shopping, dining, and world-class fishing and diving.

$1,399,500
Key Largo
Winston Waterway - MM: 102.00
3 Bed, 3 Baths, 1,224 SqFt Days Listed: 80
-9.71% ($150,500) 5 Price Changes : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.

Welcome to 233 LaPaloma Dr. The seller of this fully updated ocean side keys home has left nothing for its new owner to do but to enjoy their dream keys lifestyle. All beds and baths are on one level plus it has a large enclosed garage great for storage and bonus space. The serene setting of this home enjoys privacy provided by a lush mangrove forest canal side. Plenty of room for water toys the 60 ft dock has a newer 14k boat-lift . Many many upgrades , newer roof newer AC , impact windows and doors, kitchen , baths and flooring. Upgraded lighting and ring alarm security system. Come enjoy all the keys has to offer!

$2,399,000
Key Largo
Winston Waterway - MM: 102.00
4 Bed, 4 Baths, 2,088 SqFt Days Listed: 131
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davit Pads,Boat Lift

Come enjoy this beautiful Oceanside Waterfront & Pool home in Key Largo. This corner lot home offers 4 Bedrooms and 3 Baths, with 2088 sqft under A/C. This home was completely remodeled a couple of years ago. It also has a new metal roof, impact resistant windows and doors. It offers a large lot with 8130 sqft of land. Enjoy all the indoor and outdoor space with your family and friends. The second floor you have an open living concept with kitchen, dining, and living area, you also have a full bath and a nice bedroom. On the third floor, you have the laundry room, two additional bedrooms, and a huge master suite. Both levels have terraces overlooking the pool and the dock. By the pool you have a beautiful BBQ outdoor kitchen, TV, sitting area for entertainment, and a Jacuzzi spa. At your dock you have a 15,000lbs aluminum boat lift and two jetski floating docks. It also offers an outdoor cargo elevator for your groceries, and any other large item (1000lbs capacity) that you would need to send to the second or third floor. This property offers quick and direct ocean access thru South or North Creek, and bay access through Largo Sound and Adams Cut. In minutes you could be at all the gorgeous reefs, snorkling or fishing. This home has plenty of room for everyone. Call today!

$3,000,000
Key Largo
Winston Waterway - MM: 102.00
5 Bed, 5 Baths, 3,224 SqFt Days Listed: 19
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 50ft.

Tropical Luxury meets Coastal Living in the heart of Key Largo! Welcome to 4 Palmas, your custom-built waterfront paradise! This stunning 2-story residence, built in 2016, was thoughtfully designed for privacy, comfort & entertaining.Boasting 3,224 sqft of interior living space, this home features 5 spacious bedrooms, highlighted by 2 expansive primary suites, 1 on each level & each featuring an en-suite bathroom & oversized walk-in closets. A total of 4 full bathrooms & 1 half bath, thoughtfully distributed for comfort & convenience. With 3 distinct living rooms, 2 indoors & 1 under the covered patio & two bars, the good times never end! The open-concept living spaces flow seamlessly into approximately 2,445 sqft of outdoor living space, which includes a covered outdoor patio with a full kitchen & grills, a heated pool & spacious deck. With a combined total of 5,669 sqft, there is no shortage of space for family & friends to enjoy unforgettable gatherings or simply relax & experience the true laid-back Florida Keys island life. A short stroll leads to your 50 foot dock nestled along a wide canal which offers effortless boat access & quick navigation to the open ocean, putting world-class fishing, diving, & snorkeling just minutes away. Easily launch a kayak from the convenient floating dock & explore the tranquil mangroves of nearby John Pennekamp State Park & experience the unmatched natural beauty of this unique coastal sanctuary. Easily access our beautiful Florida Bay via nearby Adams Cut. Additional highlights include an elevator, 4 balconies, ample downstairs storage for all your water toys & an outdoor shower. 4 Palmas was modernly constructed, built to withstand a CAT 5 hurricane & features complete impact windows & doors, & a metal roof. Whether youre looking for a dream home, a vacation getaway, or a high-demand rental property, this one checks every box. Dont miss your chance to own a slice of paradise on the ocean side of Key Largo!

More Info
Most Recent Sales - (8) - Winston Waterway as of 2025-05-30
Sale Date Address Sale Price $/SF List Price Sq. Ft. Type Bd/Ba Days Listed
03-07-2025 108 8Th $2,250,000 $1,061 $2,750,000 2,120 Single Family 3/4 239
11-13-2024 188 La Paloma $1,375,000 $987 $1,375,000 1,392 Single Family 3/2 59
09-03-2024 116 5Th $1,794,000 $608 $1,949,000 2,949 Single Family 4/3 175
07-15-2024 841 Spoonbill $1,745,800 $725 $1,950,000 2,408 Single Family 4/4 119
05-23-2024 201 La Paloma $1,250,000 $970 $1,250,000 1,288 Single Family 3/2 80
04-29-2024 156 La Paloma $1,400,000 $872 $1,475,000 1,605 Single Family 3/3 75
08-15-2023 125 3rd $1,950,000 $1,262 $1,996,000 1,544 Single Family 3/2 107
07-17-2023 184 La Paloma $1,050,000 $844 $1,095,000 1,244 Single Family 2/1 117
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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 05-30-2025.
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