luxury houses for sale Monroe County, 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.

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!

This lovely Upper Keys residence, located in the sought-after charming neighborhood of Historic Tavernier, offers two bedrooms and two bathrooms upstairs and one bedroom, and one bathroom downstairs. With the Atlantic Ocean just steps away, this well-maintained home has a sense of Florida Keys charm, durability, and timeless appeal. Enjoy breathtaking ocean views from the spacious front porch, complimented with remote-controlled Armor Screens, which is perfect for entertaining guests. Downstairs, unwind in the private hot tub and seating area after a long day of fishing. A large two-door garage provides ample storage space. Outside, you will find a cozy, picket-fenced backyard that offers plenty of room to add a pool. An ocean-side community boat ramp is conveniently just steps away from your front door. This offering is centrally located between Key Largo and Islamorada and is a short commute to Miami. Don't miss the opportunity to make this adorable Keys home yours!

Located in a lovely Upper Keys neighborhood, this tastefully renovated home has everything you need! With three bedrooms and two bathrooms upstairs and a ''bonus'' room and bathroom downstairs, there is plenty of room for everyone! This home offers 2,348 SF of AC living space on a 5,000 SF parcel with a 256 SF shed, giving ample space for all your needs. On the upper level, there are two beautiful deck areas, totaling 376 SF, where you can relax after a long day of fishing! With coastal Keys finishes, concrete construction and impact doors and windows, you will feel a sense of calm as well as durability when you walk in! A convenient oceanside marina is at the end of the street offering boat rack storage and in/out service. This home is located in central Key Largo near Jacobs Aquatic Center, Key Largo Park, fishing charters, plenty of shopping, and is a quick commute to Miami. Don't miss the opportunity to make this adorable Keys home yours!

The Beach House on Sunset Road! Enjoy both sunrise & sunset from your own backyard in the Florida Keys! Welcome to a unique point of land on Florida Bay, offering two lots with almost an acre of land, a quarter-acre bay bottom and features over 200 feet of waterfront, a remodeled multi-story concrete home, a resort-style pool, dockage for multiple boats, and a sandy beach with sea oats creating an idyllic setting for enjoying the parade of boats and marine wildlife meandering by. The remodeled beach residence is situated on the southernmost lot, while the resort-style pool, framed by palm trees, is positioned on the northern lot. A gated entry and driveway lead guests to panoramic open water views across the pool and from the two-story, 4-bedroom, 2-bathroom home on two living levels. The main living level includes a kitchen, dining area, two guest bedrooms, and a full bathroom, plus three sets of French doors opening to an outside covered entertaining area. Interior stairs lead to the second living level with a vaulted tongue-and-groove open beam ceiling, a living/media room, side sitting parlor, third guest bedroom, primary suite, and an expansive upper deck for an even greater bird's-eye view of the Bay. The waterfront area includes a concrete seawall, two concrete piers, a cut-in boat slip/basin for added protection, a large Chickee Hut with picnic table, two smaller boat ramps for launching paddleboards/kayaks, and a sandy beach with wade-in beach entry. A myriad of mature palms encircles the home and pool. At night, enjoy the lighted palms as they sway in the tropical breeze, providing the ultimate backdrop for your own personal resort. This one-of-a-kind point of land on the island of Key Largo is perfectly situated to not only enjoy the most colorful sunsets by night but also the captivating early morning sunrises. Enjoy your beachfront paradise or create your vision by constructing a larger estate offering great investment potential. The choice is yours!

Experience the charm of this Key West Conch-style home on Sugarloaf Key in Indian Mound Estates. This beautifully designed residence offers two bedrooms and a half baths, with a gourmet kitchen showcasing custom cabinetry and sleek stainless steel appliances. The rich wood and tile flooring flow seamlessly throughout, adding warmth and character to every room. Unwind on the private porch off the master suite, your own secluded retreat. Recent upgrades elevate this home, featuring a durable metal roof, impact doors and windows, a modern central AC system, and a sewer hookup added in 2016. Ideally situated just 300 feet from a serene picnic area and a boat and kayak ramp, you're also only a scenic 20-mile drive away from the vibrant energy of Key West.

Charming home in a coveted Islamorada neighborhood. Welcome to your dream home in the heart of the Florida Keys! This stunning three-bedroom, two-bathroom residence boasts durable concrete construction, a new metal roof, and a host of desirable features. Step inside to discover elegant wood floors, plenty of natural light, and a cozy fireplace, perfect for relaxing evenings. The spacious garage offers ample storage and convenience. Located in a sought-after bayside neighborhood, this property provides access to an optional homeowner's membership with fantastic amenities. Enjoy features like the boat basin and ramp, or unwind by the sparkling pool. Don't miss the breathtaking bayfront sunset views that are sure to captivate. Conveniently located close to Founders Park with all the sports facilities, full marina, and host venue to town festivals. Schools and shopping, restaurants, and breweries are all on-Island as well. Experience the best of Keys living in this beautiful home—where comfort, convenience, and tropical living converge.

Great opportunity to own a concrete block home with three bedrooms on the upper level. The neighborhood is set back from US-1 and close to South Creek, offering convenient ocean and bay access by boat. The deep lot provides plenty of space for parking. Perfect for boat owners!

Conveniently located 48' dock to live aboard your boat and enjoy all the amenities that the Ocean Reef Club® offers its members. The most protected weather and security dockage on the property with easy access from the road. New Bellingham Floating Dock construction to commence in 2024. New electric, plumbing, fenders, cleats and all conveniences to help to assure boat safety. Pump out at slip by request. Fuel dock, mail service, private dining and food delivery. Transportation options and bellmen upon request for luggage or additional needs. Access to dedicated fitness center, sporting activities, fishing, diving, salon, spa, academy K-8 and so much more. Truly, this dock the highest level of unparalleled security and service.

Step into paradise with this remodeled, turn-key 3-story home, ideally situated just four houses from the stunning Florida Bay in the Paradise Point neighborhood. This pristine four bedroom, three bathroom canal-front home boasts a perfect blend of modern luxury and comfort, making it your dream waterfront retreat in the heart of Key Largo. The second floor main living level offers a beautifully designed kitchen, dining area, and living room, perfect for gatherings and everyday living. You'll also find a laundry room, a full bathroom, and a spacious bedroom. The bright and airy white kitchen features sleek quartz countertops and stainless steel appliances, seamlessly blending style and functionality. Gleaming white porcelain tiles flow throughout the home, complemented by impact-resistant windows and doors. Ascend to the third floor, where you'll discover the luxurious primary suite offering peek-a-boo water views of the sparkling bay. This level includes two additional bedrooms and another full bathroom, providing ample space for family and guests. The outdoor ground floor is a true resort-like oasis, with a beautiful granite and stainless steel summer kitchen, bar area, dining space, cozy sitting area with a TV, and ample lounging space. Enjoy endless summer days by the heated pool, surrounded by tranquil water views. Park one or two boats on your 75 feet of deep water concrete dock and seawall with davits. Keep your vehicle and gear secure in the spacious garage, providing convenience and peace of mind. Relish the coastal breeze on the expansive and new 3rd-floor outdoor porches, perfect for relaxing and enjoying the serene surroundings and sunset views. Experience the epitome of waterfront living in this exceptional Key Largo waterfront home. New AC and ''cool deck'' added since 2020. Quick ocean access via Adams Cut nearby and with this prime location, luxurious features, and impeccable condition, it's a rare find in north Key Largo!

Garden Cove's ''Southern Diversion'' is a peaceful and private North Key Largo escape, conveniently located right off John Pennekamp State Park and just a stone's throw from Ocean Reef and quick ride to South Miami. Gorgeous open water view throughout the spacious home, plus over 350' of waterfront; excellent boating location just south of Jewfish Creek Bridge for fast Ocean to Bay access. Multiple nearby fishing and dining destinations make this property all the more desirable. Protected 30' and 70' docks on the inside canal for your island living toys. The home is being offered together with additional back lot and plans for guest home, both mixed use zoned parcels allow for wedding venue and vacation rentals or to host an abundance of events and guests. Current rental income available upon request.

This side-to-slip offers protected dockage up to 48 feet with water, power and cable hook-up located on Gate House Road at Ocean Reef. Beautiful views of the Dolphin Golf Course and Dispatch Creek. A lso includes full service through the Ocean Reef Marina and a designated parking space.

E-21 is located in the Ocean Reef Club Marina with world class fishing and diving just offshore. E-21 is on the north side of E dock with 70’of dockage and a wide beam of 21'8. The 175 slip marina offers exceptional service from the dock staff, includes in-slip pump out, fuel dock, laundry facility all while being steps away from Buccaneer Island and the Fishing Village. Ocean Reef Marina is a safe and secure place to moor your vessel with 24 hour security. Experience blue-water fishing or back country flats fishing, snorkeling the reefs and everything in between. Wonderful opportunity to own a piece of paradise in the Florida Keys.

Welcome to waterfront luxury living at Buttonwood Bay Condominiums. This gated community in Key Largo is built around a deep-water coral rock harbor adjoining the Florida Bay. This residence includes a 29' boat slip conveniently located right outside your back door, providing direct access to the stunning waters of the Florida Keys. Meticulously remodeled with high-end finishes, this unit features two bedrooms, two full baths, and a half guest bath downstairs. New impact glass windows and doors flood the interior with natural light and offer breathtaking views of the marina. The floor-to-ceiling glass accentuates the beauty of the surroundings. Step into a gourmet kitchen adorned with rare blue granite, new cabinets, and state-of-the-art appliances. Community amenities include five tennis and pickleball courts, three heated swimming pools, a well-equipped fitness center, saunas, basketball, a meeting and party venue with a kitchen, eight sunset ''martini docks,'' and a rare sandy beach! A boaters' paradise, Buttonwood Bay also has a Ships Store with fuel pumps, live shrimp, ice, beverages, and snacks. There's a boat launching ramp and on-site storage areas for owners' boat trailers. Onsite management, in-house landscape and maintenance staff, and a 24/7 professional security team provide ease and peace of mind for owners. Experience a lifestyle of relaxation and recreation in this waterfront haven.

Dock slip AS-23 on Gatehouse Road at Ocean Reef Club in Key Largo offers a premier opportunity for yacht owners to experience the finest marina lifestyle. This 60' slip is perfectly situated within the exclusive, private Ocean Reef community, with direct ocean access for unforgettable fishing, snorkeling, and boating excursions. Fully equipped with 50 and 30 amps power, water hookups, and pump-out services, this slip makes living aboard your vessel seamless and convenient. Fuel is available nearby at the Main Marina, and a brand-new Bellingham Marine dock is set to be constructed in the summer of 2025. A dedicated vehicle parking spot and golf cart space is located steps away from your slip. Ocean Reef Club is celebrated for its comprehensive lifestyle offerings, including a state-of-the-art fitness center, numerous dining options, two championship golf courses, a 175-slip marina, a medical center, and a robust lineup of cultural and social events. With round-the-clock security and exceptional services, Slip A23 provides a safe, comfortable, and sophisticated home base for enjoying the best of the Florida Keys yachting lifestyle.

Discover the ultimate boater retreat in beautiful Summerland Key! This stilted canal-front home features three bedrooms and two baths and easy access to both the Atlantic Ocean and Gulf of Mexico. After a day on the water, unwind in the pool or relax under a palm tree in your hammock. The ground-level storage area is perfect for your boating gear and outdoor furniture. A commercial ice maker is ready to chill your catch of the day or beverages for your sandbar excursions. Enjoy the convenience of a Coast Guard-marked channel, providing a safe and enjoyable transit to and from your dock. The wide 60-foot canal makes maneuvering a breeze, and marine fuel is just 2 minutes away by boat—no more long trips to the fuel dock. Inside the home, you'll find an open-concept design centered around the kitchen, dining room, and living area. Off the dining room is a screened-in porch, perfect for enjoying happy hour cocktails or taking in another incredible sunset in paradise. This home boasts three generously sized bedrooms, two baths, and a laundry room. Recent upgrades include a new AC system installed in 2022, a new water heater in summer 2024, and a new roof added in 2018. The furniture can be sold with the home, making it move-in or rental-ready! The home is conveniently located near many stores, restaurants, and other conveniences. This location offers everything you need in tranquil Summerland Key. This home is truly a boater's dream!

Experience this exquisitely renovated waterfront residence. This home epitomizes functional elegance highlighted by contemporary coastal design. The terrace overlooking the canal offers peek-a-boo Gulf views and serves as an excellent outdoor living space. Inside, you'll find impeccable updates, including quartz countertops, LVP flooring, recessed lighting, and Calacatta marble tiled showers. Ascend the interior staircase to the main living area upstairs where you will find your kitchen, living room, three bedrooms, one bonus office or guest room, and two full bathrooms. Step outside to the generous covered porch, where you can unwind and soak in captivating vistas of the canal and the picturesque bay beyond. The property offers 60 feet of protected concrete dockage, complete with a 20,000 lb. boat lift for swift boating access to the Atlantic or Gulf. Additionally, a versatile bonus flex space downstairs offers boundless opportunities to customize according to your lifestyle. This refined coastal retreat epitomizes luxury and convenience, inviting you to make it your own.