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Florida Keys Waterfront Homes on the Bay / Gulf Side of the Island For Sale

Total Listings 241
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$4,700,000
Key Haven
Key Haven 10th Add   - MM: 5.00
5 Bed, 5 Baths, 4,480 SqFt Days Listed: 234
-17.47% ($995,000) 3 Price Changes : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.

Fully renovated in the last 4 years, this 5-bed, 5-bath, exquisite gated estate with its brand new resort-style pool, and Chefs kitchen boasting new Sub-zero, Wolf, and Miele appliances, offers 2 master suites on the 3rd floor with a private balcony and new interior 3-story elevator! This waterfront Key Haven estate offers a full length concrete dock and 15K lift, while the stunning indoor/outdoor integration invites you to savor the idyllic surroundings. The 4,500 SF of luxurious living space harmonizes with the tranquil beauty of its environment, featuring breezy outdoor spaces and light-filled interiors. Every detail has been thoughtfully designed for refined living, from the Hubbardton Forge lighting to the expansive walls of impact windows that frame breathtaking views of the turquoise Gulf waters. Enter through a grand entryway with a sweeping staircase and elevator into a spacious Great Room perfect for entertaining. The Chefs kitchen is a culinary masterpiece, equipped with high-end, stainless appliances, striking quartz countertops with a waterfall edge, and a breakfast area offering picturesque canal views. Dine in the elegant dining room or al fresco on the sprawling waterfront covered veranda. Guests will revel in the comfort of three well-appointed en suite guest bedrooms, one equipped with a steam shower, while you retreat to one of two third-floor primary suites, featuring spa-inspired bathrooms complete with Hansen & Bringle cabinetry, expansive walk-in showers, and terrace perfect for soaking in Keys famous sunsets. For added convenience each floor includes a laundry area and kitchenette, making lifes conveniences just steps away. After a day on the water, dock your boat, take a refreshing dip in the brand new custom pool, or cook your fresh catch in the outdoor kitchen. Situated within a peaceful, established neighborhood yet just minutes from the magic of Key West, this one-of-a-kind Caribbean masterpiece has it all.

$4,721,000
Lower Matecumbe
Port Antigua   - MM: 74.05
5 Bed, 5 Baths, 4,463 SqFt Days Listed: 261
-9.58% ($500,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,None,Boat Lif

This exceptional Port Antigua residence, located on a tranquil cul-de-sac, boasts over 220 feet of concrete dockage including two boat lifts and a davit. As you enter through the exquisite hand-carved mahogany doors, youre greeted by a welcoming foyer with sliding glass doors that open to the pool and dock area. The elegant, curved staircase ascends to the main living area, featuring a spacious open-concept layout and a gourmet kitchen equipped with stainless steel appliances. The living side of the house includes two bedrooms, two bathrooms, and a laundry room, while a raised walkway leads to a secluded primary suite with a luxurious bathroom and an expansive dream closet. For those seeking sun and relaxation, the pool and hot tub provide the perfect retreat, complemented by a travertine pool deck and a brick-paved outdoor bar area, complete with a DCS grill and side burner. This shaded oasis is ideal for crafting tropical drinks and grilling your daily catch. Adjacent to the bar is a convenient pool cabana with a full bathroom. When its time to unwind indoors, head to the third floor, where a theater and game room await, complete with a wet bar and a popcorn machine. Two stunning stained glass windows depicting sea life add a unique touch, reminding you of the adventures that await on the water. The third floor also features a bedroom and a half-bath, along with an open lanai offering glimpses of the Atlantic. The expansive dock includes two gazebos--one for relaxation and the other for fish cleaning--along with a davit and two boat lifts, accommodating 20,000 lbs. and 12,000 lbs. Ample space between the lifts ensures room for your cruising yacht. This home is truly a unique gem in Port Antigua. Dont miss the opportunity to make it yours.

$4,750,000
Plantation Key
Plantation Key Colony   - MM: 90.00
4 Bed, 4 Baths, 4,144 SqFt Days Listed: 60
-4.04% ($200,000) 1 Price Change : Last Change 10 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift

Discover coastal luxury in this stunning 4-bedroom, 4-bathroom bayside paradise. With 4,144 square feet of luxurious living space, this home offers breathtaking sunset views and direct access to the sparkling waters of the Florida Keys. Indulge in spacious, open-concept living areas, perfect for entertaining guests. Retreat to one of two primary suites, each featuring a large walk-in closet and private en-suite bathroom. Ascend to the rooftop deck and be rewarded with unobstructed, open-water bay views. The property features a separate living space, ideal for in-laws or guests, offering privacy and independence. The modern kitchen boasts sleek stainless steel appliances, double oven, gas appliances and ample counter space, perfect for culinary enthusiasts. The homes durable construction, including CBS, metal roof, and impact-resistant windows and doors, ensures peace of mind. For added security and privacy, the property is fully fenced and features an electric gate. Enjoy panoramic water views and unforgettable sunsets from your private oasis. With large boat dockage, youll have plenty of room for multiple boats, jet skis and easy access to the open water for boating, fishing, and other water activities. This completely updated home offers the ultimate experience in comfort and convenience. Whether youre seeking a serene retreat or an active water lovers paradise, this home has it all. Dont miss this opportunity to own a piece of paradise.

$4,950,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,100 SqFt Days Listed: 77
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 70ft.

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout.Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation.On the main floor, the gourmet kitchen is a chefs dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock.This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

$4,975,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
3 Bed, 3 Baths, 1,264 SqFt Days Listed: 235
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Come home to outstanding views with 109 feet of bay frontage in Lower Matecumbe Key. This cottage-style home combines all of the elements of Florida Keys charm with captivating open water views and is situated on 1.3 acres of land. Complete with three bedrooms and two bathrooms, this ground-level, and updated residence is the perfect place to entertain while basking in all of the beauty the Keys offers. Zoned residential estate, this income-producing home qualifies for weekly rentals, which provides ample opportunities for a discerning buyer.

$4,995,000
Big Pine Key
Pine Channel Estates   - MM: 29.50
4 Bed, 4 Baths, 3,727 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits332ft.Concrete

Experience the Pinnacle of Coastal Elegance in Big Pine Key!This openwater masterpiece designed by noted architect Glen Gray, is where modern luxury meets tropical serenity. This luxurious 4-bedroom, 4 1/2 -bathroom estate is a testament to impeccable design and indulgent living. Step inside and be greeted by soaring cathedral ceilings, walls of glass, and an open floorplan that flows seamlessly through grand living spaces. A chefs kitchen, outfitted with Viking appliances, custom hickory cabinetry, and granite countertops, is both a culinary haven and a design showpiece. Two spacious ensuite bedrooms and a private study or media room grace the main level, while the second-floor primary suite is a sanctuary of its own, featuring a spa-inspired bathroom, a loft sitting area, and a private balcony with sweeping open water views. A personal elevator connects all levels, ensuring effortless access, while the detached 936 sq. ft. guest cottage--connected by a covered breezeway--offers a private retreat complete with a kitchenette, wraparound balcony, and great room. The outdoor oasis is nothing short of breathtaking. A sparkling custom concrete pool and hot tub, controlled by Aqualink remote systems, sit amid lush tropical landscaping, providing a resort-like setting for relaxation or entertaining. The estates extensive 332-ft concrete seawall includes two sets of boat davits, a fish-cleaning station, and swimming access, making it a boaters paradise with direct access to pristine waters. No luxury has been overlooked--impact windows and doors, a whole-house generator, and ADT remote security provide peace of mind, while the three-zone A/C system ensures comfort year-round. Situated just 30 miles from Key West and mere minutes from Looe Key Reef, this waterfront estate is your gateway to the best of the Florida Keys lifestyle. Immerse yourself in unrivaled luxury and coastal living-schedule your private tour today.Video: https://n9.cl/flythrough-29433-enterpris

$4,999,500
Big Pine Key
Pine Channel Estates   - MM: 29.50
4 Bed, 4 Baths, 2,812 SqFt Days Listed: 67
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift50ft.

LUXURY LIVING IN THE LOWER KEYS where the pace of life is a bit slower, and the fishing and diving are exceptional. The 16,875 sq. ft. property features 150 ft. of frontage along a 46 ft. wide canal, a 50 ft. concrete dock, and two boat lifts (the larger lift is 21,000 lbs.) Its a private, tropical setting where one can relax under the tiki or in the heated, salt system pool, enjoy down time in the hot tub, and entertain on the primary canal-side porch overlooking protected lands across the canal to the north. This impressive home offers 2812 sq. ft. of living area and an open floor plan with cathedral ceilings, wall-to-wall glass doors and windows in the great room, a formal dining area, a study that can easily be a fourth bedroom, and a master suite with water views. For guests theres a two-bedroom, one-bath wing boasting its own laundry room and canal-side porches. 3-zone central air and heat. Spacious two-car garage and ample ground level storage; plenty of space for guest parking and room to park your motor home and boat trailer. Fly privately into the Marathon International Airport or commercially into Key West International Airport.

$4,999,999
Shark Key
Shark Key   - MM: 11.00
5 Bed, 5 Baths, 6,325 SqFt Days Listed: 376
-27.54% ($1,900,001) 3 Price Changes : Last Change 119 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 75ft.

An Exclusive Waterfront Estate for the Discerning BuyerA rare opportunity awaits in the prestigious, gated enclave of Shark Key--an ultra-private oasis where security, exclusivity, and luxury converge. This meticulously designed 6,325 sq. ft. estate, set on nearly an acre of lush tropical grounds, offers a lifestyle of unparalleled refinement.Beyond its impact-rated windows, high-elevation construction, and full-house generator, this residence is engineered for year-round security and peace of mind. The 5,000 sq. ft. enclosed garage--complete with two car lifts, space for five vehicles, and an expansive workshop--caters to collectors and enthusiasts alike.Breathtaking panoramic views of the Gulf of Mexico unfold from nearly every vantage point, enhanced by a private dock, Tiki hut, outdoor kitchen, and an expansive covered veranda--the perfect setting for hosting unforgettable sunrise and sunset soirees. A grand pool, elevator access to all floors, and multiple outdoor entertainment spaces further elevate the experience.Inside, soaring ceilings and open, light-filled living spaces create an atmosphere of effortless elegance. The spacious en-suite bedrooms are designed for privacy and comfort, including a palatial 800 sq. ft. first-floor primary suite--a true sanctuary.With pricing well below the appraised value of $6,700,000 and the lowest price per square foot on recent record, this estate represents an extraordinary investment in one of Floridas most coveted waterfront communities--just 10 miles from Key West International and private airports.This is more than a home; its a statement of success. The opportunity to own this legacy property at 55 Two Turtles Lane wont wait. Will you?

$4,999,999
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 4,732 SqFt Days Listed: 21
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Modern Coastal in Buccaneer Point Estates. This bay front solid CBS home tucked away near the end of a private street offers unparalleled privacy and the sought-after allure of waterfront living. Experience a masterpiece built to incorporate and withstand natures elements. Interior and features that draw on the natural backdrop fusing coastal design w/contemporary architecture. Upon entering the residence and ascending the stairs, panoramic waterfront views unfold across the entire home through floor-to-ceiling windows. Fluidity in design is the essence of the concept for this home. The kitchen is adorned with opulent finishes including sleek quartz countertops, lacquer kitchen cabinets, a natural wood island, recessed lighting, and Thermador appliances. This home offers 5 bedrooms, 3 full bathrooms, and 3 half bathrooms. Two spacious bedrooms share a bathroom on the main living level with an additional half bath in the hallway and additional 2 bedrooms located on the third floor share an adjoining bathroom. The primary suite features floor-to-ceiling windows overlooking the bay, two private balconies, an office nook, and a resort-style bathroom. Notable features in the primary suite include a custom walk-in closet, a dual entry rain shower, a stand alone jet tub, and marble tile throughout. Continue up the stairs to access the rooftop terrace where you can enjoy 360 degree sunset views, soak in the hot tub, entertain guests, and serve drinks from the enclosed wet bar! Complete with an elevator accessing each floor up to the third story. Outdoor amenities include an in-ground pool, artificial turf grass, mature landscaping, cabana pool space, a two-car carport, charging station and a pier dock offering deepwater dockage for all your vessels including a 20,000 pound lift and jet ski lift. This location offers unparalleled boating access with close proximity to Adams Cut & Tavernier Creek for ocean access. We invite you to experience the epitome of coastal living.

$5,495,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 2,972 SqFt Days Listed: 283
-15.46% ($1,005,000) 6 Price Changes : Last Change 40 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip40ft.

STUNNING PANORAMIC BAY VIEWS, sunsets and unparalleled privacy. This once-in-a-lifetime bay front property offers 200 feet of shoreline on Florida Bay with spectacular views. The property encompasses 2 and 1/2 lots, totaling a stunning three-quarters of an acre. The meticulously landscaped grounds, tended to by a Florida Master Gardener, provide a lush backdrop to the spacious residence. Boaters will love having a flats boat right behind the house along with TWO slips in the private marina just 800 feet from the front door. Each slip accommodates a boat to 40 LOA. Lifts allowed. Youll have immediate bay access and quick ocean via Snake Creek. At the heart of the estate, a sprawling one-level residence provides effortless living and lots of room for friends and family. An elevator provides easy access for everyone. A soaring cathedral tongue-and-groove ceilings create an airy sense of space, while oversized windows frame panoramic bay views from every angle. The living, dining, and kitchen areas seamlessly blend together, providing the perfect backdrop for entertaining or simply enjoying quiet moments with loved ones. A spacious screened porch offers a second living and dining area overlooking the bay. The primary suite boasts more breathtaking bay views and offers a peaceful retreat at the end of each day. Across the home, a separate wing awaits, ideal for hosting friends and family. Here, a large office, a cozy family room, and two additional bedrooms with en-suite baths provide ample space for guests to feel right at home. Youll find 3,000sf +/- under AC along with many, many additional outdoor living spaces. Additional square footage includes a 562sf workout room and a 1500sf garage (huge!) with a workshop and golf cart garage. Youll have PLENTY of space for cars, hobbies and storage. Almost all of the windows are impact and a 2003 5V crimp Galvalume metal roof provides peace of mind. Sellers have Army Corps and DEP approval for 60 observation pier!

$5,499,000
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 3,906 SqFt Days Listed: 239
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Enjoy this OPEN WATER luxury lifestyle in the coveted area of Buccaneer Point Estates in south Key Largo. Prepare to be captivated by this 5 bedroom, 4 bath extraordinary waterfront masterpiece that combines modern elegance and over 3,900 sq. ft of living space with a tropical paradise ambiance. Nestled on the shores of the bay, this custom-designed home has been thoughtfully crafted with discerning clients in mind. This rare offering promises a lifestyle beyond compare, where every moment is infused with the allure of the Florida Keys. As you step inside, ascend the interior stairs from the grand foyer to the main living level, where cathedral ceilings and an abundance of natural light create an inviting atmosphere. Revel in the breathtaking water views framed by expansive windows and doors, seamlessly blending the beauty of the outdoors with the comfort of your luxurious sanctuary. The heart of this residence lies within the great room, where a well-appointed double island creates the perfect setting for entertaining while the expansive porch areas beckon you to soak in the tranquil vistas. Designed to accommodate a large family or gathering of friends, this home boasts two master ensuites on each level, ensuring privacy and comfort for all. In addition, three guest bedrooms with adjoining bathrooms provide ample space for everyone to unwind and recharge. For water enthusiasts, this home is a dream come true with an inviting in-ground heated pool, surrounded by a custom paved deck area and lush privacy landscaping. The deep water pier dock features a boat lift and jet ski lift. The spacious four-car garage with dual doors, a second refrigerator, an ice maker, and the potential for a bar or summer kitchen makes it a versatile space for hosting unforgettable backyard gatherings.

$5,499,000
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 4,822 SqFt Days Listed: 83
-1.79% ($100,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip2

Luxurious Florida Keys living awaits in this stunning 5-bed, 5-bath estate with 4,822 sq. ft. of living space and a total building area of 10,791 sq. ft. The first floor has a 1,300 sq. ft. of legal enclosure included and an office on the 3rd floor that can be converted into a 6th bedroom. Designed for comfort and elegance, this home features high ceilings, 8-ft. doors, and spacious interiors.A private, fenced yard with two electric gates and an intercom system ensures security, while a heated pool and jacuzzi offer resort-style relaxation. The grand entrance is flanked by two car garages with electric doors and a covered car porch, each with a 36 keyed door. Enter through the foyer to a striking staircase or an 8-ft. elevator providing access to all levels.The main living area features 20-ft. ceilings, breathtaking bay views, and an open floor plan. A chefs kitchen boasts an original Benihana cooking station, top-tier appliances, and ample storage. This level also includes a laundry room and two guest bedrooms with a shared bath.Upstairs, the master suite offers his & hers walk-in closets, a spa-like bath, an office, and a media room with surround sound. The 2,500 sq. ft. rooftop terrace showcases 360-degree panoramic views and stunning sunsets.For boating enthusiasts, the 225-ft. private Bayfront pier includes a 25,000-lb. boat lift and additional docking space.Experience the pinnacle of luxury in this Florida Keys retreat--a rare opportunity to own paradise!

$5,750,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
5 Bed, 5 Baths, 3,597 SqFt Days Listed: 102
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. A recently sold $3.5M, 4000 sq. ft. home was torn down just to obtain a buildable lot on Hilton Haven. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock while overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75 by 300 bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living rooms custom hand built beamed wood cathedral ceiling and a majestic staircase. The current sunroom, converted into a dining room, features French doors that open to views of the pool and harbor. The expansive deck leads down to the lower entertaining level. The chefs kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to the rear private deck and dock. Completing the first floor are the laundry room, a half-bath, a full bath, and a charming guest bedroom. The sunroom with a wet bar and bathroom provides access to the one car garage, and second staircase leading to the second-floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. https://show.tours/e/4vNFpvG

$5,895,000
Key Largo
Sunset Point   - MM: 95.00
4 Bed, 4 Baths, 1,872 SqFt Days Listed: 217
-4.15% ($255,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat SlipC

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 birds-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 - the choice is yours! Duplicate Listing, MLS #613012.

$5,900,000
Marathon
Crains Subdivision   - MM: 58.00
3 Bed, 3 Baths, 1,352 SqFt Days Listed: 350
-25.79% ($2,050,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 40ft.

This magnificent 10-acre waterfront parcel offers a rare opportunity to own a genuinely extraordinary slice of paradise with a building right! Situated in a prime location, next to a bird Sanctuary. Build your forever home surrounded by stunning panoramic water views of the Gulf of Mexico on both sides, so you are not on a highway. There is also a small private beach located on the property. There is ample space to build your dream oasis with endless possibilities. This lot is part of the City of Marathon and will allow 7-day rentals should you wish to make this an incredible vacation retreat. Curry Hammock State Park is located on the opposite side of Overseas Highway. This park is the largest undeveloped parcel of land between Key Largo and Big Pine Key.For those with a vision, inquire today!

$5,950,000
Marathon
Crains Subdivision   - MM: 58.00
3 Bed, 3 Baths, 5,220 SqFt Days Listed: 39
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin

Nestled on a secluded 2-acre lot in Grassy Key, Marathon, this gated waterfront estate boasts 5,220 sq. ft. and is highlighted with a ton of amenities including two docks, 4 post boat lift, private sandy beach and an infinity-edge elevated pool blending seamlessly with the gulf and featuring a built-in table and chairs for relaxing or entertaining. Expansive covered areas by the pool offer shaded spots for lounging and has direct access to the living areas. Double entry doors with intricate carved wood details welcome you into a light-filled home. The open-concept living area is graced by large windows and sliding glass doors that frame panoramic views and create a seamless connection between indoors and outdoors. A striking marble fireplace serves as the focal point. Every element of this home reflects thoughtful design, from the impact-rated doors and windows, in-house elevator plus marble floors, exquisite cabinetry, and refined finishes enhancing the homes timeless appeal. The main kitchen is a chefs delight, featuring granite countertops, two wine coolers, and abundant cabinetry. A cozy dining nook encased in windows offers stunning gulf views, creating the perfect setting for every meal. The primary suite is a sanctuary of luxury, featuring panoramic gulf views, a two-sided fireplace, and direct access to the pool. The en-suite bathroom offers a private sauna, jetted tub, walk-in shower, and makeup counter, creating a spa-like retreat. The guest quarters are designed for comfort and independence, offering a morning kitchen and two guest suites. Each suite includes its own en-suite bathroom and generous closet space, ensuring privacy and convenience for visitors. The large office can also serve as a 4th Bedroom. Additional amenities include a home theater room complete with reclining seats and bar plus an oversized 3-car garage with lift.

$5,999,000
Big Torch Key
Misc Big Torch Key   - MM: 28.00
4 Bed, 4 Baths, 4,315 SqFt Days Listed: 248
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: DavitsConcrete

Perhaps the largest residential property in the Keys, this sprawling Big Torch Key estate offers a coveted 12+ acres and incomparable 2,000 ft of waterfront, with concrete dock, davits, and boat house! Unbeatable access to both the Atlantic and the Gulf from deep Blue Fish canal! Relax and unwind with incomparable privacy at this unique estate, surrounded by nature. The home is an expertly designed fusion of Key West character and Old Florida charm. The open main living space is flooded with natural light and thoughtfully oriented to take full advantage of prevailing sea breezes. The space is ideal for entertaining with generous living and dining rooms blending harmoniously with an open chefs kitchen, boasting abundant cabinetry, large pantry, and premium appliances. Linger around the table with friends in the adjacent dining room or dine al fresco on the massive patio, complete with stunning Views of Niles Channel! Plans in place for a luxurious Infinity Pool to be built off of the living room of the main house, which will feature stunning Open Water Views! Seller to begin build pending DEP permit. A large guest bedroom and additional private guest house provide comfortable accommodation for visitors. A cherry wood staircase nestled in the heart of the home leads to a private main suite, with walk-in closet, en suite bathroom, stunning panoramic views of the Open Water, and private garden terrace, the ideal backdrop for enjoying peaceful Sunrise Views. A rooftop observation deck provides unobstructed views from Port Pine Heights to Cudjoe Bay. Equipped with impact windows, a whole-home generator, cisterns and elevator for added convenience. The lush topical grounds are adorned with a plethora of tropical trees such as plumeria and canary island palms. Toast to your dream Keys lifestyle from the comfort of a seaside tiki hut, the perfect place for enjoying Keys Famous Sunsets. Dont miss the opportunity to see this truly unique Keys paradise!

$6,350,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
6 Bed, 6 Baths, 4,700 SqFt Days Listed: 5
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.Concr

Welcome to Mykonos Villa, a luxurious 6-bedroom, 7.5-bathroom estate in Islamorada, FL. This home features an open layout with natural light, sleek finishes, and refined design.The gourmet kitchen, with a La Cornue stove, high-end appliances, and custom cabinetry, flows seamlessly into the living and dining areas, perfect for entertaining. A smart home system manages temperature, security, and pool features.Each bedroom includes a private en-suite bathroom. The master suite offers breathtaking views, a private balcony, spa-inspired bathroom, and spacious walk-in closet.Outdoors, enjoy a pool, hot tub, kitchen, 100 feet of private dockage, two boat lifts, and a fish cleaning station.Mykonos Villa--Live where the ocean greets luxury, and paradise is your everyday address.

$6,350,000
Lower Matecumbe
Lower Mat Harbor   - MM: 75.00
4 Bed, 4 Baths, 3,228 SqFt Days Listed: 566
-15.33% ($1,149,999) 3 Price Changes : Last Change 33 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

$400,000 PRICE REDUCTION !! ... Welcome to Serenity Cove, a remarkable, comfortably luxurious estate set along the shores of the Florida Bay. This custom-designed property, stretching from the highway to the bay is almost 1.75 acres. It is perfect for those who value peace, relaxation, and the simple joys of what the Florida Keys has to offer.This home offers four bedrooms and four bathrooms and 110 of dock with multiple slips accommodating up to a 45 boat with 5 draft and 16k lift. This home has been thoughtfully designed with tasteful moldings, and warm, inviting finishes. The kitchen, is equipped with top-tier appliances, custom cabinetry, and a roomy island - perfect for those who love to cook and entertain. It smoothly transitions into the formal dining room, making it an ideal space for both quiet family dinners and larger celebrations.The second-floor suite, with its spacious layout, welcoming fireplace, and private balcony, is the ultimate retreat. The en-suite bathroom, has a dual vanity, a claw-foot soaking tub, and a walk-in shower, guarantees moments of relaxation.The first floor offers a smart design with separate living areas and bedrooms. The 1st floor suite includes a steam shower and a reinforced safe room that doubles as a walk-in closet. The additional two bedrooms and a den with surround sound and a wet bar are comfortably located on the opposite side of the home.Enjoy quiet moments on the covered patio or engage in lively gatherings around the spacious poolside patio, which leads directly to the sandy beach for amazing sunsets. Here, youll find ample seating, a fire pit, a Boat House and steps leading to the basin for swimming and exploring the Bays unique ecosystem.Serenity Cove is comfortably tucked away from the hustle of US1, offering a sense of privacy and security, while maintaining easy access to schools, shopping, dining that make Islamorada so desirable.

$6,390,000
Key Largo
Tarpon Acres   - MM: 102.00
5 Bed, 5 Baths, 2,364 SqFt Days Listed: 169
-4.48% ($300,000) 1 Price Change : Last Change 57 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Basin

Welcome to the ultimate tropical sanctuary in Key Largo! An extraordinary waterfront estate with two homes, spanning over 2.5 acres along Tarpon Basin. This breathtaking property offers unparalleled sunset vistas, a coral jetty framed by a lagoon, a boat ramp, lush mangroves, and a canopy of majestic mahogany trees.Green sloping land is elevated for privacy and optimal protection . The estate features two impeccably remodeled homes with high-end finishes. The main house includes three bedrooms, four elegantly appointed bathrooms, a full kitchen, and spacious living areas. The second home offers two beautifully crafted bedrooms, two luxurious bathrooms, and a full kitchen. Both homes are adorned with lavish spa-like bathrooms and hand-carved, imported Bali doors and casings.The Suburban/Commercial Zoning offers limitless investment possibilities, or a private sanctuary, a high-end vacation rental, an exclusive event venue, or a family compound. Imagine creating an oversized dream home surrounded by tropical splendor.Just 65 minutes from Miami International Airport, this one-of-a-kind estate is perfect as a peaceful hideaway, a lucrative income property, or a stunning family compound. Create your private sanctuary and embrace the essence of the Florida Keys lifestyle.

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 01-30-2025.
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