Upper Florida Keys Real Estate for Sale, Homes and Condos in the Florida Keys

INVESTORS! BUY the LOWEST PRICED Beach and Sunset Bay home in Buccaneer Point! Welcome to a life of serenity, sophistication, and waterfront bliss at 39 N Bounty Lane! This peninsula in Buccaneer Point Estates was developed to create a sense of privacy, in a peaceful bay unique to the Upper Keys. The estate-sized property has 80 of shoreline directly on the Florida Bay with deepwater dockage. This custom three-story, CBS waterfront home offers four bedrooms and three bathrooms with over 3,015 square feet of living space. As you step through the grand interior staircase entry, you are greeted by a seamless flow of space and light, enhancing the homes airy and inviting ambiance as you walk up to the main level. Expansive sliding doors and porches throughout the home offer breathtaking bay and sunset views. The gourmet kitchen is equipped with stainless steel appliances, granite countertops, a large laundry room doubling as a walk-in pantry and an elevator lift outside the dining area. The main living level features one guest bedroom and bathroom with a walk-in closet. Ascending to the third level, you will find three additional bedrooms and two bathrooms. The ensuite primary offers panoramic bay views from the private balcony. Immerse yourself in the private and spacious backyard, where mature palms and landscaping provide ultimate tranquility. Lounge in the hot tub, launch a paddle from your beach, or sit by a fire and savor the soothing sounds of the tropical breezes. With room for an in-ground pool and summer kitchen, the possibilities of creating your dream space are endless. The exterior is adorned in coastal blues and whites, and echoes the iconic color palette of the Greek Isles, creating a timeless sense of serenity. Boaters will delight in the pier dock, boat lift, and central location for quick oceanside access. This is a rare and great investment opportunity to own on one of the most coveted streets in Key Largo.

A Secluded Waterfront Paradise in the Heart of the Florida Keys. Step into a world of minimalistic elegance and tranquility at this one-of-a-kind coastal oasis. Tucked away on over an acre of lushly landscaped, private property stretching from highway to water, this architecturally unique home offers serene luxury and endless possibilities. Arrive via a tree-lined driveway to discover a striking three-story coastal retreat. Featuring four private en suite bedrooms, each with its separate entrance, the home is designed to provide privacy and relaxation for family and guests alike. The sleek, contemporary design integrates seamlessly with the natural surroundings, offering captivating water views from every vantage point. Designed with entertaining in mind, this property boasts multiple spacious outdoor entertainment areas, including verandas overlooking the sparkling pool, sand-laden grounds, and tranquil waterfront oasis. Gather around the expansive fire-pit with seating for up to 14, perfectly situated at the waters edge for unforgettable evenings under the Keys starry skies. Adding to its versatility, a secondary garage structure--measuring over 700 sq. ft. with soaring 11-foot ceilings--has been artfully re-imagined as a flexible guest space or personal retreat.With SR zoning permitting vacation rentals, this unique property offers endless opportunities, whether as a family compound, corporate retreat, or lucrative investment. Its layout, designed to maximize privacy and individuality, makes it especially appealing for those seeking a distinctive and adaptable space.Additional features include:Potential for docking a houseboat or watercraft, as previously enjoyed. Ample parking and storage, ideal for all your waterfront toys. A kayakers or paddleboarders dream, with access to nearby mangrove trails.A secluded yet accessible location, offering privacy while remaining close to the best of the Keys.Dont miss the opportunity to own this ..

*PRICE REDUCED* Welcome to your private waterfront sanctuary in Key Largo, offering expansive open water views from every room. This CBS-constructed home features 3 bedrooms, 3.5 bathrooms, and 2,466 square feet of living space, with an additional 900+ square feet on the lower level. A whole-house generator with automatic switch-over ensures uninterrupted power, complemented by a new 1,000-gallon propane tank installed in 2024.The kitchen is designed for entertaining, equipped with a 5-burner DCS cooktop, Viking range hood, convection microwave, additional full size freezer, and a countertop ice maker. The outdoor space is a true retreat, featuring a custom 35,000-gallon saltwater pool with a sun shelf, built-in spa section, and a 4-ton heat pump for year-round comfort. Electronic controls and auto-fill make pool maintenance effortless.For boating enthusiasts, the 65-foot dock includes two boat lifts, one rated for 10,000 lbs and the other for 7,000 lbs. Additional amenities include a putting green with two chipping areas, two tiki huts (one custom with a sprinkler system), ample parking for boats, RVs, and water toys, an electric carport windscreen curtain, and multiple storage areas, including a permanent shed and a queen-size Murphy bed for guests.An elevator provides easy access between levels, while a solar-assisted hot water heater (new in 2024) and dual A/C units with new condensers (2024) enhance energy efficiency. The property is exceptionally private, surrounded by concrete privacy walls and a secure gate, and is adjacent to a protected mangrove preserve that will never be developed.Agent related to owner.

A Must See!! Completely remodeled property located in Ocean Isles Estates. Breathtaking open water views, Rare 2 car garage with plenty of extra parking space, waters edge pool, 17k lbs. boat lift, impact windows and doors, metal roof, 2 master suites, Remodeled 1 bedroom/1bath on lower level, recreation area, and much more. Pictures coming Soon!!

This immaculate bayfront home, built in 2018, is a true waterfront dream. Boasting 4 spacious bedrooms and 2.5 luxurious bathrooms, this property seamlessly blends comfort and convenience. With an elevator providing easy access to all levels, all-impact windows and doors, and outdoor hurricane wind-rated enclosure screens, this home is as durable as it is beautiful. The backyard is a coastal masterpiece, opening up to breathtaking views of Sunset Cove and Pelican Key. Stunning skies and tranquil waters set the stage for your ultimate Keys lifestyle. For boating enthusiasts, this property is a haven! It features a private dock with water, electric, and security cameras, a 16,000-pound boat lift, an additional smaller lift, a davit, and a convenient fish cleaning station. With no mangroves obstructing your view, your access to adventure is immediate and effortless. After a day on the water, unwind in the multi-lighted saltwater pool with an integrated jacuzzi or watch the illuminated marine life beneath the surface as the sun sets. The vibrant coastal lighting adds a magical touch to your evenings. Privacy and security are top-notch with a fully fenced property and a LiftMaster electric gate offering offsite control and monitoring capabilities for peace of mind. The low-maintenance tropical landscaping completes this serene retreat. Move-in ready, this home is waiting for you to embrace the Keys lifestyle in luxury from day one. Dont miss this opportunity to live the dream on the water! (MIA about a hour away)

Discover unparalleled luxury and island charm in this beautiful resort-style home located on Plantation Key. Step inside to find a spacious lower-level entertainment area complete with a full kitchen, bedroom, bathroom, and living space that opens to a lush backyard featuring a heated pool, 65 feet of concrete dockage with two boat lifts (10K & 20K), and a summer kitchen equipped with a wet bar and built-in BBQ. Upstairs, accessed by a custom internal staircase, youll find a gourmet kitchen with premium cabinetry and appliances, a stunning primary suite, and two additional guest bedrooms. The air-conditioned garage offers convenient storage for your boating gear and includes a commercial-sized ice maker. This home truly checks all the boxes for island living. Dont miss your chance to own this exceptional property!

Introducing a bespoke bay front residence on Mutiny Place in Buccaneer Point Estates, never before on the market. Situated on the point of Mutiny Place, this property exudes exclusivity with a perfect balance of seclusion, accessibility, and breathtaking views. Encompassing just over half an acre along the serene Florida Bay, this property boasts bay and lake access, a private boat ramp, and unobstructed sunset vistas year-round.Privacy envelops this estate-sized lot, featuring meticulously landscaped grounds that showcase native and mature flora, including countless unique palm varietals, trees, and grass, framing this coastal haven. Bask by the heated resort-style pool, unwind in the captivating Zen garden featuring a fire pit, and unwind under the pool-side tiki hut. Possibilities for more structure exist on the large lakefront lot by separating the 2 parcels.The residence is a thoughtfully designed three-bedroom, three-bathroom home with an open floor plan and interior stairs. Key features include pristine hardwood floors, split bedrooms on the main living level, hardwood cathedral ceilings with endless bay views, a secluded master suite occupying the entire third story, and twelve-foot-wide porches. Complete with Andersen impact sliding doors, PGT impact windows, and a new metal roof. Boating enthusiasts will appreciate the convenience of a 9k boat lift on a deep water pier dock and a private boat ramp for launching skiffs, paddles, and kayaks. Quick oceanside access north and south through Adams Cut or Tavernier Creek. Immerse yourself in the epitome of coastal luxury and tranquil living at 81 Mutiny Place.

Fabulous Port Antigua home with over 135 ft. of protected dockage is ready for a new family to enjoy! This stunning 4-bedroom, 3.5-bath home boasts 3,332 square feet of luxurious living space and offers everything you could ever desire. As you step inside, the warm and inviting atmosphere will welcome you home. With bay views from the third floor living area this residence truly embodies the Florida Keys lifestyle. The very large chefs kitchen is a masterpiece of design and functionality. With an open floor plan that seamlessly connects the kitchen to the dining and living areas, youll never miss a moment with family and friends. For the avid boater, this property is a dream come true, featuring over 135 feet of dockage, complete with 2 boatlifts and 2 fish cleaning stations. Spend your days on the water, fishing, diving or enjoying boating to your favorite restaurant. Once youre back home and need some shade, your private tiki hut awaits, providing the perfect spot to relax and unwind.This home has been thoughtfully designed with convenience in mind. Youll find an elevator for easy access to all levels, making your life here a breeze. And to top it all off, the Port Antigua community offers a private homeowners park with a bayfront sandy beach and a boat ramp. No other community in the Keys offers these amenities.Dont miss your opportunity to own this piece of paradise. Your dream home in Islamorada awaits, where the Florida Keys lifestyle becomes your everyday reality. Start living your best Keys life!

This 4-bedroom, 5-bathroom gated estate is a true gem, offering a luxurious and private waterfront lifestyle. Perfectly situated on a corner lot, it boasts breathtaking open bay views of Blackwater Sound, providing a serene and scenic backdrop. Inside, the home features a Hausscape-designed Italian chefs kitchen, equipped with premium appliances such as a Sub-Zero refrigerator, Wolf 30-inch gas cooktop, and an icemaker -- ideal for both culinary enthusiasts and those who love to entertain.The property also includes detached guest quarters, providing a private and comfortable space for visitors. The outdoor space is equally impressive, with a sparkling pool, attached jacuzzi, and an expansive area for relaxation and gatherings. Boating enthusiasts will appreciate the propertys remarkable waterfront features, including over 220 feet of boat dockage and two boat lifts, making it a perfect retreat for those who enjoy the water. This home offers the ideal combination of sophistication, comfort, and convenience in a truly exceptional setting.

The Ospreys are back! Welcome to The Ospreys Nest; your perch by the Ocean in one of Islamoradas most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20 dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story primary suite and beachside pool with heater and chiller for those hot summer days. True island living is here on Sunset Drive. Listing includes canal parcel with dock across the street RE#00389220-000100

SPECTACULAR COMPOUND! Two Freestanding CBS Waterfront Estate Homes Combined. 3/3 & 4/3.5. This Luxurious compound has the potential for two upper main living areas as well as four separate units. Two Boatlifts, & Separate Davits 120 sq. ft. of dockage. Roof Top Raised Garden & Hot Tub w/ Direct Ocean Views. The Kitchens Boasts Stainless Steel Appliances, Granite Counter Tops. 700 sq. ft. under AC for FANTASTIC workshop & up to 6 +cars. Plenty of room for a Pool, Storage, Gym, Playroom & Water Toys. Covered Fish Station, High-Capacity Ice Machine. Fishermens Dream House w/ Direct Ocean Access. **2** Houses for the price of one. Lush Tropical Landscaping. & Fire Pit. Owner is also selling his 33 Custom made Offshore Express Grady White with Tuna Tower & Jet ski. Islamorada Pool Architectural Design & Plans already completed & available ready to build. Centrally located near Shopping, School & Restaurants. Close to John Pennekamp Coral Reef State Park. This is a must see!!!

Unobstructed SUNSET/BAY views. Tucked away on a secluded point in the prestigious Sunshine Estates community on Plantation Key. Expansive property. Well built CBS home designed to enjoy bay views from essentially every room in the house. 4 Beds 4.1 Baths. Vaulted ceilings finished with wood beams. Refinished custom oak wood floors, corian kitchen countertops, dummy waiter, marble bathrooms/bedrooms, built in shelving and and uniquely designed glass block to reflect the colored sunsets. Large floating wood deck surrounded by lush foliage ; for morning coffee or catered events. Ground level consists of covered parking & rec room/maid quarters w/cabana bath & kitchen for indoor-outdoor entertaining. Crystal clear water, fishing, lobstering, & water-sports right in your own backyard. Quick ocean access via Tavernier Creek. Centrally located to restaurants, schools, shopping, churches & hospital. This is the home you have been waiting for!**BUYER TO VERIFY ALL INFORMATION.**

Discover Coconut Cottage, Your Tropical Paradise in Islamorada! Coconut Cottage beckons you to the quintessence tropical living in Islamorada. This oceanfront haven boasts a 90ft. Sandy Beach, a boat basin, and an inviting waterfront pool, creating an idyllic backdrop for both relaxation and adventure. The main residence, featuring 4 bedrooms and three bathrooms, exudes vintage Florida coastal comfort. The charm of the property is further enhanced by a screened-in porch, where one can savor panoramic ocean vistas and gentle sea breezes.A separate one-bedroom, one-bath guest cottage offers additional privacy and comfort, making it ideal for hosting friends and family. Constructed with durability in mind, both homes feature concrete walls and metal roofing, ensuring a sanctuary that stands the test of time.The propertys lush tropical landscaping and gated entry promise a secluded retreat, fully fenced to ensure your exclusive slice of paradise remains undisturbed. Ample parking accommodates a fleet of cars, boats and trailers, while a dedicated storage shed keeps your water toys, lawn essentials and fishing gear organized.Coconut Cottage isnt just a residence; its a lifestyle choice for those who dream of natural tropical setting. Envision your special day at this perfect wedding venue, where a 7-day rental policy aligns seamlessly with celebrations and gatherings. With a charming Boutique Hotel nearby, your guests will enjoy the convenience and luxury that this unique property affords.Discover the rare gem that is Coconut Cottage, a treasure nestled in one of Islamoradas most sought-after locations, where every day feels like a blissful escape from the ordinary! Truly a rare find!

Welcome to the hidden gem of Buccaneer Point, where luxury meets sustainability! This fully solar-powered home boasts breathtaking 360-degree views, perfect for entertaining while ensuring your privacy. The open floor plan and large porches seamlessly blend indoor and outdoor living. The chefs kitchen is a culinary dream, equipped with top-of-the-line appliances, expansive quartz countertops, and ample storage. Each bedroom showcases modern design and spacious comfort, with the primary suite thoughtfully located in a separate wing for ultimate tranquility and stunning views. Step outside to your private outdoor oasis, featuring a rooftop terrace ideal for relaxing or hosting gatherings, all while soaking in spectacular sunrises and sunsets. The property also includes a large pool, jacuzzi, boat ramp, and a spacious dock and 2 boatlifts making it easy to embrace the Florida Keys lifestyle. Dont miss your chance to own this extraordinary retreat!

In the heart of Plantation Key lies a magnificent custom-built five bedroom. five bathroom waterfront home with a guest home, like no other. This resort-style oasis, crafted with the unyielding strength of CBS construction, and all impact glass windows and doors, it boasts an expansive custom 52 heated, salt generation system pool that beckons you to dive in and soak up the sun. With 144 feet on the water of the prestigious Trout Creek basin, this home is a boaters paradise, with expansive views, and is located just a stones throw away from the renowned Tavernier Creek, and gateway to the Atlantic Ocean.This estate, completely reimagined and expanded in 2006, sits on a double lot in the exclusive Sunshine Estates neighborhood, offering unparalleled luxury and sophistication. As you step inside, this home it invites you to relax in style. The open-concept design seamlessly blends indoor and outdoor living, creating a space that is perfect for entertaining guests, or simply enjoying your private haven.The master suite is a true sanctuary, with a spa-like bathroom and a private balcony overlooking the glistening waters of the basin and bay. There is a large artists studio, drenched with ambient light, along with the master suite that encompasses the entire third floor. Each of the additional bedrooms offers plenty of space and lavish amenities, ensuring that every guest feels pampered and indulged.As you step outside onto the expansive decks, you are greeted by freshening breezes and the gentle rustle of palm trees. The massive pool sparkles in the sunlight, beckoning you to take a refreshing dip or lounge in the shade of the pool-house cabana. With over 140 feet of dock space, you have ample room to accommodate all of your water toys, from sleek yachts to personal watercraft. Additional features include custom auto-gated double gate entryways, paver drives, a 12,000-pound boat elevator, award winning landscape, & sunset views. Welcome to paradise

Are you tired of waiting for Uber? Dont want to risk a DUI? Make this your bayfront estate and enjoy all that Islamorada has to offer. Just steps from MEAT, Shima and Marker 88 restaurants and just down the street from City Hall Cafe! Fully fenced for privacy, this property offers breathtaking bay views and an irreplaceable tiki at the end of the dock. You will make this your daily sunset viewing platform! Upstairs you will find a large open living area with sliding glass doors to the spacious screened terrace. In addition there are 3 bedrooms and 2 baths. From the terrace there are stairs to the pool and then the backyard, beach and dock. The ground level includes 2 bedrooms and bath plus an open living area. You will fall in love with this property and want to make it your Keys retreat or an investment opportunity to rent when you are not using it.

Absolute showstopper with 150 of frontage overlooking some of the most pristine bay waters the Keys has to offer. Complete nut and bolt renovation with no corners cut. Deep water dockage for almost any size boat and access through Channel 5 to hit the ocean. The upstairs main living area offers 3 bedrooms/2 bathrooms, high-end kitchen appliances, and turquoise water views from almost every room. The downstairs separate guest quarters offers 1 bedroom/1 bathroom, living room, and kitchen. Pool permit in place or take a dip in the bay. This ones special, so dont miss the opportunity to be one of the cool kids.

Panoramic Bay and Sunset Views! Breathtaking Bayfront Home in Safety Harbor.Experience the stunning beauty of panoramic bay views from this exquisite bayfront home in the premier Safety Harbor neighborhood on Lower Matecumbe. This home is in pristine condition and features an irreplaceable cut-in boat slip with a composite dock on the bay ensuring that your views are not obstructed, and providing immediate bay access and quick ocean access via the two bridges at Channels 2 and 5.Inside, youll find four spacious bedrooms and three bathrooms, perfect for comfortable living. An enclosed garage for all of your fishing and diving gear. The home is equipped with a new whole house generator, ensuring uninterrupted power.Step outside and immerse yourself in resort-style living with a luxurious pool and spa, lush low maintenance landscaping, perfect for relaxation and entertaining. Enjoy breathtaking sunsets year-round from your own private oasis either at the tiki bar, the dock, or one of the two bayfront screened porches. Dont miss the opportunity to own this exceptional bayfront home in Safety Harbor. Schedule your private showing today!

Timeless Waterfront Charm in Venetian Shores, Islamorada - Indulge in classic charm with this meticulously positioned waterfront residence in sought-after Venetian Shores. A dream come true for those who appreciate spectacular sunsets and unparalleled boating opportunities in the Florida Keys. Step into the gracious embrace of a bygone era in this residence poised directly on Snake Creek, the gateway to the Atlantic Ocean and Florida Bay, with prime fishing, diving, and waterfront dining just minutes away by boat. A celebration of classic waterfront living, the homes first floor unfolds with a spacious split plan, showcasing a large living room with a dining area, a family/game room blessed with water views on three sides, a water-view kitchen, and a central sunset-view screen porch. Three bedrooms, including two master suites--one featuring a private waterfront porch--and three full baths (two en suite), harmoniously combine casual refinement and comfort. Ascend a spiral staircase to the crown jewel--a top floor with panoramic water views, private balconies, and limitless possibilities. This space transforms into a fourth bedroom suite, a guest efficiency, or the grandkids playhouse, complete with a kitchenette, dining area, seating space, beds/bunk space, a full bath, and two closets. Moor your boat in the protected cut-in boat slip with davits. Delight in the waterside deck and Tiki hut, ideal for fishing or grilling, all while enjoying passing boats, dolphins, and sea life. Additional amenities include an outdoor shower, two carports, a storage/tackle room, covered seating and an elevator lift to the main floor. Recent upgrades include new storm shutters throughout and new impact windows to fortify the stairway tower. These enhancements add to the aesthetic appeal and are also crucial for windstorm insurance. This waterfront haven isnt just a residence - its a lifestyle. Seize this once-in-a-generation opportunity to make this dream lifestyle your own.

Welcome to your dream retreat on the bay in Venetian Shores - the Upper Keys favorite boating neighborhood! Boaters of all kinds will love the immediate bay access and lightning-quick ocean access via Snake Creek. With breathtaking views of the Florida Bay, and a sparkling pool, its the perfect place for relaxing and soaking in the sunshine. This stunning three-bedroom, two-bath beach has undergone a massive and stylish recent remodel. Youll love the timeless, modern coastal touches including the stunning new flooring! Vaulted ceilings and huge impact windows let the sunshine in. The homes open-concept design showcases panoramic bay views from almost every room. Each bedroom offers comfort and tranquility, with the master suite enjoying its own serene water views. Nestled on a dead-end street with only 12 homes, youll enjoy privacy galore. Keep a boat on the floating dock behind the house or in your boat slip just steps away, providing easy access to the crystal-clear waters of the Florida Keys. Whether youre looking for a peaceful escape or an active waterfront lifestyle, this property has it all--privacy, luxury, and unparalleled access to the best of Islamorada. Dont miss this rare opportunity to own a piece of paradise! Metal roof, impact windows and doors & artificial turf make maintenance a breeze. Electric fence. Boats to 40 and lifts allowed!