luxury houses with pool for sale Summerland Key, United States

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.

Welcome to your personal paradise, where island living becomes a reality. Imagine a backyard that isn't just an ordinary backyard, but a breathtaking tropical oasis with a private pool and serene spaces perfect for unwinding and relaxing. This luxurious retreat includes a gorgeous 3-bedroom, 2.5-bathroom single-family home with a versatile den that can serve as a home office, music room, or gym--offering the ultimate blend of comfort and sophistication.Tucked away in the most exclusive section of the Key West Golf Club, your new home is set behind a second gate, providing access to the prestigious Sanctuary community. The spacious, open-concept design flows seamlessly through the newly remodeled kitchen, dining, and living areas, making it perfect for hosting family and friends. The kitchen is a chef's dream, boasting stainless steel appliances, quartz countertops, and abundant storage. Step outside to your private pool for a refreshing swim or unwind on the screened patio while watching the sunset, surrounded by lush tropical landscaping. As a resident, you'll also enjoy access to two sparkling community pools, a fitness center, and a butterfly garden--all within this secure, gated community.Located just minutes from the vibrant center of Key West, you'll have easy access to local shops, restaurants, and beautiful beaches, embracing the island lifestyle. Don't miss the chance to make this slice of paradise your own--schedule a private showing today!

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.

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).

Talk about views! This waterfront property offers breathtaking panoramic vistas of Key West Harbor and the historic waterfront area. Additionally, it boasts beachfront and water panoramas from every room within the house. This dramatic and sophisticated residence spared no expense.

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.