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

Total Listings 344
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$4,400,000
Key Largo
Buccaneer Point   - MM: 98.00
4 Bed, 4 Baths, 2,658 SqFt Days Listed: 56
-2.22% ($100,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp

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!

$4,495,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 2,304 SqFt Days Listed: 365
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits96ft.Concrete

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.

$4,499,000
Marathon
Crains Subdivision   - MM: 58.00
6 Bed, 6 Baths, 5,757 SqFt Days Listed: 38
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

Tropical Bayfront Estate nestled into almost 2 lushly landscaped private acres with 3 building rights included! Everything you could possibly need is right here! Main House, Guest House, Pool, Pool Apartment, Storage Building, Dock, Boat Basin, Boat Ramp, Boat lift, and UNBELIEVABLE never-ending turquoise sea views! Well-appointed details found throughout the main home include soaring wood planked ceilings. Spacious kitchen featuring granite counters, upgraded stainless steel appliances, island, and built-in cabinetry and bar plus a separate dining room. The Master Retreat encompasses the entire second floor with a grand Master Bathroom featuring double vanity sink, and soaking tub overlooking the bay, and a comfortable loft; the perfect vantage point for taking in the stunning Open Water Views. Plenty of room for all with two en suite guest bedrooms, and a home office which could easily be converted to a third guest bedroom. Outside the main house, youll find an attached pool house with its own entrance, and additional living space and guest bedroom, as well as a private guest cottage, separate from the main residence. The main house is CBS construction, with impact doors and windows, with a new metal roof in 2021. Peace and privacy abound at this exemplary Marathon paradise! Dont miss this must see property!

$4,500,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 1,846 SqFt Days Listed: 70
-7.22% ($350,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip40ft.

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!

$4,721,000
Lower Matecumbe
Port Antigua   - MM: 74.05
5 Bed, 5 Baths, 4,463 SqFt Days Listed: 228
-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.

$4,800,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 946 SqFt Days Listed: 7
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 55ft.

This remarkable 32,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay.One of the key highlights of the lot is its exceptional dockage, which has previously accommodated a 36-foot boat, making it perfect for boating enthusiasts. The dock can be expanded to suit your needs, providing ample space for additional vessels or watercraft. The property also offers plenty of room for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds creating a tranquil atmosphere for evening relaxation.The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aqatic species like fish, birds, manatees and a mulitude of different birds. Zoned as Residential Estate, this property allows for weekly rentals, presenting an opportunity for investment or personal use. Its a perfect canvas for your dream residence or vacation retreat.With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this lot is one of the best properties on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation.Owner / Agent

$4,950,000
Plantation Key
Plantation Key Colony   - MM: 90.00
4 Bed, 4 Baths, 4,144 SqFt Days Listed: 27
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: 44
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: 202
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: 30
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits300ft.Concrete

Welcome to your dream home in the heart of Big Pine Key designed by renowned architect Glen Gray. This magnificent 4-bedroom, 5-bathroom estate offers an unparalleled blend of luxury and comfort. Step inside to discover an open floorplan that seamlessly connects the living, dining, and kitchen areas, creating a perfect space for both entertaining and everyday living. The spacious, well-appointed kitchen features modern appliances, ample counter space, and a large island, making it a chefs delight. Adding to the convenience and luxury, this home features a personal elevator, providing easy access to all levels and ensuring that every part of your estate is just a button-press away. A whole house generator, impact doors and windows and concrete construction to give you peace of mind. The property has ADT Control for remote access of the security system and door locks. Your private outdoor oasis awaits with a sparkling pool with Aqualink remote pool controls (also transferrable), inviting hot tub, and a beautifully paved patio, perfect for relaxing or hosting gatherings. The lush landscaping and serene surroundings provide a sense of tranquility and privacy. Additionally, this estate includes detached guest quarters connected by a covered breezeway, offering a private retreat for visitors or an ideal space for a home office or studio. The paved driveway and carport offer ample space for all your vehicles and recreational equipment. In the backyard, you can entertain family and friends or head out on the water with access to some of the best boating the Florida Keys has to offer. With over 300 feet of concrete seawall, youll have plenty of room for all your watercraft, complete with two sets of boat davits, a fish cleaning table, and a ladder for easy swimming access. This Big Pine Key estate is not just a home; its a lifestyle. Experience the best of Florida Keys living with this exquisite property. Schedule your private tour today and make this paradise your own

$4,999,500
Big Pine Key
Pine Channel Estates   - MM: 29.50
4 Bed, 4 Baths, 2,812 SqFt Days Listed: 34
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: 343
-27.54% ($1,900,001) 3 Price Changes : Last Change 84 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 75ft.

This is a brilliant opportunity to grow your wealth with pricing well-below the appraised value ($6,700,000.00) and lowest ($790.5) PPSF on record! Situated along Two Turtles Lane in the gated enclave of Shark Key, this 6,325 square foot estate is the definition of luxury living. Nearly an acre of lush tropical landscaping, waterfalls, fountains and vistas elevate this private retreat. The Impact windows, high elevation build, and House Generator, promise security and comfort year-round. Enjoy panoramic views of the Gulf of Mexico from your private dock, Tiki hut, outdoor kitchen, and sunsets from your enormous covered veranda. A grand pool, an elevator to each floor, and multiple outdoor entertainment spaces, all add to the checklist of conveniences. The interiors are enhanced by soaring ceilings, spacious living areas, large bedrooms with en-suite bathrooms including an 800 square foot, first floor Primary Suite. The 5,000 sq. foot enclosed-garage with two car lifts accommodates 5 vehicles plus an enormous workshop. With its prime location and amenities, this estate at 55 Two Turtles Lane stands as a testament to refined coastal living in one of Floridas most coveted communities and all just 10 miles from Key Wests International and private airports.

$4,999,999
Key Haven
Key Haven 10th Add   - MM: 5.00
5 Bed, 5 Baths, 4,480 SqFt Days Listed: 201
-12.20% ($695,001) 2 Price Changes : Last Change 154 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.

$5,495,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 2,972 SqFt Days Listed: 250
-15.46% ($1,005,000) 6 Price Changes : Last Change 8 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: 206
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.

$5,599,000
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 4,822 SqFt Days Listed: 50
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip2

Experience the lavish charm of the Florida Keys in this meticulously crafted 5-bed, 5-bath,with an office that can be converted into a 6th bedroom. This 4,822 sq. ft. home designed with your comfort in mind. Ideal for large families, it boasts spacious interiors, elegant high ceilings, and 8 ft. door openings. A grand entrance reveals a vast private fenced yard, equipped with 2 electric gates and an intercom system for seamless communication. Adorned with stylish pavers, the yard includes a heated pool and jacuzzi area.Approaching the main entrance, discover car garages on either side with electric doors and a car porch, each featuring a private 36 keyed door. Enter the foyer to find a striking staircase or opt for the 8 ft. tall elevator, leading to the main floor or a guest room with pool access. The main floor boasts an elegant living and dining room with a 20 ft. ceiling and breathtaking bay water views. The kitchen features an original Benihana cooking station, top-of-the-line appliances, and ample storage, accompanied by a spacious laundry room. Two guest bedrooms with a bathroom complete this level.Ascend to the third level, revealing a master suite with a spacious bathroom, his and hers walk-in closets, an office, and a media room with surround sound. The pinnacle of luxury awaits on the 2,500 sq. ft. rooftop, offering 360-degree views, including stunning bay and sunset views. Accessible via stairs, it boasts tasteful balconies for a delightful experience.For boating enthusiasts, the property features a Bayfront 225 ft. pier with a 25,000 lbs. boatlift and ample space for watercraft. Live the life of opulence in this Florida Keys retreat!

$5,695,000
Key West
W C Maloney Diagram   - MM: 2.00
6 Bed, 6 Baths, 4,182 SqFt Days Listed: 12
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to a truly one-of-a-kind historic masterpiece in Key Wests coveted Meadows neighborhood. This exquisite estate seamlessly blends timeless charm with modern luxury. Nestled on a rare 11,200 sq. ft. lot, the property offers over 4,180 sq. ft. of living space, including a detached one-bedroom guest quarters, creating the ideal balance of comfort, style, and functionality.Stepping onto the grounds, youre immediately transported to a serene tropical oasis surrounded by meticulously designed landscaping featuring mature native foliage and aromatic tropical plants. At the heart of the backyard lies an expansive saltwater pool and spa with a cascading waterfall, framed by historic Key West curbstones. Durable Ipe wood decking and a spacious patio enhance the estates natural beauty and functionality. A lighted gazebo with a built-in grill and cabinetry provides the perfect setting for outdoor dining and entertaining.Inside, the homes historic elegance is unmistakable. Soaring 14-foot coffered ceilings, intricate crown molding, and original wood floors reflect masterful craftsmanship. The gourmet kitchen is a chefs dream, overlooking the pool and outdoor spaces. It features a six-burner Viking stove, dual ovens, dual dishwashers, and a 1,000-bottle wine cellar--ideal for both intimate gatherings and formal entertaining.Privacy and tranquility abound throughout the estate. The separate one-bedroom guest quarters offer a secluded retreat for visitors, while a luxurious steam room elevates relaxation. Every detail has been thoughtfully curated to preserve the homes historic character while enhancing modern comfort.Ideally located in a prime historic neighborhood, the estate is within walking distance of the vibrant Historic Seaport, Key West Bight Marina, Atlantic beaches, and Duval Streets renowned dining, shopping, and nightlife. This legacy property is more than a home--its a true piece of Key West history in a setting that simply cannot be duplicated

$5,750,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
5 Bed, 5 Baths, 3,597 SqFt Days Listed: 69
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

$5,950,000
Marathon
Crains Subdivision   - MM: 58.00
3 Bed, 3 Baths, 5,220 SqFt Days Listed: 6
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.

$5,995,000
Key Largo
Sunset Point   - MM: 95.00
4 Bed, 4 Baths, 1,872 SqFt Days Listed: 184
-2.52% ($155,000) 1 Price Change : Last Change 87 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 offering great investment potential. The choice is yours!

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 12-28-2024.
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