Luxury houses with pool for sale Stock Island, United States

Welcome to an unparalleled waterfront experience in one of the most coveted locations in Key West. Located on the prestigious Riviera Canal, this one-of-a-kind four-bedroom, two-bath haven is more than just a home—it's a boater's dream, a sunseeker's paradise, and the ultimate indoor-outdoor luxury living. Imagine waking up each morning in the heart of this island gem, with 80 feet of wide canal frontage just outside your door, complete with a 20,000 lb boat lift and davit ready for your larger vessel. Whether you're setting sail for a day on the water or simply soaking up the tropical vibes, this home puts you right where the action is. Designed by the famed Bender & Associates, this 2,426 sq. ft. retreat was built to blend the best of coastal living with modern comfort. The split floor plan gives everyone their own space to unwind, while the open-concept living area beckons you to gather and celebrate the good life. With wall-to-wall sliding glass impact doors and travertine floors throughout, your living space seamlessly merges with the outdoors, bringing in natural light and the gentle canal breeze. And speaking of the outdoors... step into your own private oasis! A sparkling pool, surrounded by meticulously maintained landscaping, is the perfect spot for a lazy afternoon dip. Prefer a sunset barbecue? Your covered outdoor dining and lounge area sits on sleek travertine floors, with plenty of space to relax rain or shine. The kitchen is a showstopper, featuring quartz countertops, custom cabinetry, and stainless-steel appliances, perfect for whipping up fresh seafood feasts or hosting cocktails at the bar with a view of the pool. The primary bedroom is the ultimate retreat, with its own seating area and French doors that open right onto the pool deck. Additional features include a whole-house Generac generator, impact windows and doors throughout, and a gated circular driveway that offers complete privacy.

Tranquil well maintained home professionally decorated on a private island five minutes off of Key West, on Sunset Key. Tropical island living at its finest. The island has beautiful sand beaches, community resort style pool, tennis courts, fitness center, full service spa and an ocean front five star restaurant/bar. This exclusive private community is dreamy and very secure, with the ferry service to and from Key West running 24 hours. Experience the serenity of truly being away from it all while just a short ferry ride to all that Key West has to offer. Great investment opportunity for a vacation rental, the rental history can be provided.

Welcome to 1409 4th Street - an exceptional four-bedroom, three-bathroom compound that is a legal duplex. The main home spans 2004 square feet with 2 bedrooms and 2 bathrooms, offering expansive living areas and a spacious kitchen with the potential to add a third bedroom. Adjacent is a separate 2-bedroom, 1-bathroom home that would make for an ideal guest house or income-producing rental. The homes sit on a large 10,000 sq. foot corner lot in the desirable and very convenient midtown area. Outdoor entertaining opportunities are limitless in the large, low-maintenance yard that features a pool area just steps from the kitchen. Tucked away there is a tranquil garden with an avocado tree that provides a perfect hidden retreat. Don't miss out on owning one of Key West's most versatile properties!

An exquisite two-story home in the Meadows, newly built in 2017. The custom craftsmanship and attention to every detail will satisfy the most discerning buyer. This four bedroom, three and a half-bath home has all the modern high-end finishes while maintaining its old Key West charm. A large corner lot with off-street parking boasts lush landscaping in a private setting with a heated/cooled saltwater pool and waterfall. All hurricane-impact windows an doors along with a generator that covers the entire house. The home is fully insulated making it soundproof. This is a very rare opportunity to own something new in Old Town with all the current building standards met. This home is being offered completely furnished, including the artwork throughout.

Step into a piece of Key West history with this fully renovated, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this legal duplex offers endless possibilities. Whether you're looking for a wise investment, a vacation getaway, or a new primary residence, this property is ready. Live in one unit and rent the other, or enjoy the entire home yourself! There is an interior staircase to enter the upstairs unit. Each spacious level features two bedrooms, one bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool—perfect for relaxing and entertaining. The upper unit boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Both units come fully furnished, and the upstairs unit has a long-term tenant, ensuring immediate rental income. Located in a prime spot close to the Old Seaport, with top restaurants and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!

Charmingly restored and updated historic home on a quiet street in the heart of Old Town, one of the best neighborhoods. This island oasis is spacious with plenty of storage and ample off street parking. The master bedroom with ensuite bath is on the first floor. There is plenty of room to entertain around the pool or relax on the front porch. The property is very private with a lush tropical landscape, visible from the open kitchen which has accordion hurricane impact windows and a full size hurricane impact pocket door that transforms the inside to outside.

Charmingly restored and updated historic home on a quiet street in the heart of Old Town, one of the best neighborhoods. This island oasis is spacious with plenty of storage and ample off street parking. The primary bedroom with ensuite bath is on the first floor. There is plenty of room to entertain around the pool or relax on the front porch. The property is very private with a lush tropical landscape, visible from the open kitchen which has accordion hurricane impact windows and a full size hurricane impact pocket door that transforms the inside to outside.

Discover the epitome of unique luxury in the Florida Keys with the REAL Southernmost House of the Continental United States of America, a property that perfectly blends history, elegance, and an unrivaled location. Positioned adjacent to the iconic Southernmost Point buoy, where the Atlantic Ocean meets the Gulf of Mexico, this concrete 4,008 sq ft home stands as a landmark at the southernmost edge of the Continental United States on a large 17,000 sq ft lot. This multi-family designated home boasts five bedrooms and five and a half bathrooms. Enjoy the charm and elegance of a historic home with modern amenities. As you enter through the front door into a formal living room, you are transported back to the Hemingway era. The formal living room opens up to a Florida room with tropical vibes, and glass sliding doors lead to the pool area. The kitchen and living-dining room feature an open concept and beautiful wooden cathedral ceilings. The kitchen is a chef's dream with ample open space, a large counter, restaurant-style stainless steel double Viking stove/ovens with a large hood, and a Sub-Zero fridge. The home also features sealed coral stone flooring. From the living room, an elevator leads to the upstairs primary bedroom and two guest bedrooms, surrounded by a large balcony with endless vistas over the property and the Atlantic Ocean. Enjoy swimming in a beautiful large 50 x 20 ft. pool, and the spacious outdoor lounging area with Ocean breezes. Bird-watching will be your new favorite pastime. With its unique location, this property offers unparalleled ocean views and proximity to all of Key West's vibrant attractions. The Southernmost Beach is on the same block, with its sandy beach and restaurant. The property has a coveted transient license, allowing for nightly rentals, making it a prime investment opportunity for vacation rentals or a lavish private residence. The REAL Southernmost House is a rare gem in the heart of Key West. Part of the property needs complete renovation, and the 1930 sq ft seawall requires partial restoration. The property comes with an approval letter from the Army Corps of Engineers for a dock of 665 square feet (6-foot wide by 32-foot long access walkway and a 10-foot by 47-foot long platform).

Located in the prestigious Truman Annex community, this town home in The Foundry is the perfect getaway offering the perfect blend of luxury, comfort, and convenience. This beautifully designed 2-bedroom, 2.5-bathroom home enjoys a highly desirable location with easy access to Key West's vibrant Old Town, while maintaining privacy and security within a gated community. As you step inside the spacious open-concept living area you will find 11 foot high ceilings, impact rated windows and glass doors that bathe the interior with natural light, and updated finishes throughout. The kitchen has been recently updated with all stainless steel appliances. Moving up stairs, the master bedroom is a private sanctuary featuring an ensuite bathroom. A private balcony off the master suite offers a peaceful retreat to enjoy the island breeze. The guest bedroom is up one more floor and is equally inviting with its own ensuite bathroom ensuring privacy and comfort for visitors. Stand out features of this town home include its street facing orientation, not something all homes in The Foundry have. The town home also has its own carport with additional storage above- a highly convenient feature few have and holds a value in excess of $75,000. Finally, The Foundry has its own pool, reserved for use by only Foundry owners and their guests. With a strong rental history and a Truman Annex Special Transient License, this home is an excellent investment opportunity. The license allows for short-term rentals with restrictions, providing flexibility and a steady stream of income when the property is not in use. Whether you're seeking a full-time residence, a seasonal escape, or a profitable rental investment, this townhome provides the ultimate opportunity to experience the best of Key West living.

Tall about views! This three-bedroom, three-bathroom oceanfront home has incredible panoramic views of the Key West Harbor and the historic waterfront. No expense was spared on this elegant Sunset Key private residence. This home has it all, from hardwood and tile floors throughout, to a chef's kitchen with granite counter-tops, comfortable living and dining area, a covered outdoor patio, and an in-ground pool. Sun Set Key Private Island is only three minutes from historic downtown Key West by an island ferry which runs 24 hours a day and leaves from the Opal Key Resort and Marina. Walk to one of the island's three beaches. Even though it is an off-shore island, Sunset Key Island has full city utilities and service, and amenities such as tennis, a full-service spa, and gourmet restaurant.

This is the ultimate living experience. You get all Historic Key West has to offer, but are tucked away on your own private island paradise. Access to Sunset Key is by the island ferry which runs 24 hours a day, but is only a 4 minute boat ride. Have all the fun you can stand in Key West, but then come home to absolute peace and quiet. Have your own Sunset Party from your covered rooftop observation deck. The island has all the conveniences of a world class luxury resort, including three beaches within a minutes walk, a full service spa, golf cart parking, gourmet restaurant, tennis courts, and much more. Ample covered parking is available at discounted rates in the Opal Resort parking garage. For a truly unique and eye opening experience, call now and make an appointment for a private grand tour of the island. You will be glad you did!

Tranquil well maintained home professionally decorated on a private island five minutes off of Key West. Sunset Key. Tropical island living at its finest. The island has beautiful sand beaches , community resort style pool, fitness center, tennis courts , full service spa and a ocean front five star restaurant and bar. This exclusive community is dreamy and very secure. the ferry service to and from Key West runs 24 hours. Experience the serenity of truly being away from it all while just a short ferry ride to all Key West has to offer. Great investment opportunity for vacation rental, history can be provided.

If island living is your dream, 39 Cannon Royal Drive in Shark Key is the perfect place to make it a reality. Located in one of the most exclusive and sought-after gated communities in the Florida Keys, this Caribbean-inspired estate offers a tropical escape like no other. Set within this private community, the home boasts stunning, panoramic waterfront views of the Gulf of Mexico, all while being just minutes from the vibrant energy of Key West. The moment you step inside, you're greeted by soaring ceilings and a grand staircase, offering a dramatic entry to the open-concept living spaces. Every corner of this home is designed to maximize its breathtaking surroundings, with the primary bedroom, kitchen, and living areas all enjoying expansive water views. This tropical retreat offers 3 spacious bedrooms, a dedicated office, and the rare convenience of a garage—blending luxury and practicality seamlessly. Outside, the inviting pool serves as your personal oasis, while the prime waterfront location opens the door to endless adventures. Boating, paddleboarding, and kayaking are just steps away, with space to keep a flats boat for easy access to sandbars and world-class fishing. Whether you're searching for a winter retreat or a year-round sanctuary, 39 Cannon Royal Drive is the ultimate escape to island paradise. Shark Key amenities include tennis courts, pickleball courts, swimming lagoon, clubhouse and a private beach.