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

Total Listings 319
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$4,499,000
Marathon
Crains Subdivision   - MM: 58.00
6 Bed, 6 Baths, 5,757 SqFt Days Listed: 6
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
Key Largo
Buccaneer Point   - MM: 98.00
4 Bed, 4 Baths, 2,658 SqFt Days Listed: 24
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!

$4,721,000
Lower Matecumbe
Port Antigua   - MM: 74.05
5 Bed, 5 Baths, 4,463 SqFt Days Listed: 196
-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
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 1,846 SqFt Days Listed: 38
-1.03% ($50,000) 1 Price Change : 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!

$4,950,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,100 SqFt Days Listed: 12
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: 170
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: 169
-9.17% ($504,000) 2 Price Changes : Last Change 7 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: DavitsConcrete

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: 2
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: 311
-27.54% ($1,900,001) 3 Price Changes : Last Change 43 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: 169
-12.20% ($695,001) 2 Price Changes : Last Change 137 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.

$5,499,000
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 3,906 SqFt Days Listed: 174
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.

$5,500,000
Plantation Key
Edenaire   - MM: 90.50
4 Bed, 4 Baths, 2,652 SqFt Days Listed: 154
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip1

Welcome to the good life on Tavernier Creek and the prestigious Tide Avenue! This is the perfect setup for avid boaters and those seeking the pinnacle of Keys living. Situated on a section of the creek with an amazing view down a side creek. As you enter through the gates of this expansive property, youll find a paver driveway leading to a two-car garage. The main living area on the second floor features a grand living room with vaulted exposed wood beam ceilings, impressive new kitchen, 3 bedrooms and 2 bathrooms, and an elevator. The ground level includes a separate guest quarters with 1 bedroom, 1 bathroom, a kitchen, and a stunning bay window with bench seating to take in the outdoors. Screened-in covered multi-purpose area on the ground level for entertaining. The property boasts new upgrades including: metal roof, impact windows & doors, kitchen, air conditioner, and heated pool. It also offers one of the best dock setups on the Creek, with 2 boatlifts and ample space for friends to visit as they navigate this major waterway. Whether youre shrimping off the dock in the winter or lobstering among the rocks in the summer, Tide Avenue captures the essence of the Islamorada lifestyle.

$5,550,000
Key West
Sunset Key   - MM: 0.00
3 Bed, 3 Baths, 1,927 SqFt Days Listed: 275
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Othe

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

$5,599,000
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 4,822 SqFt Days Listed: 18
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!

$5,750,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
5 Bed, 5 Baths, 3,597 SqFt Days Listed: 37
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, gas fireplace, 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
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 2,972 SqFt Days Listed: 218
-9.31% ($605,000) 2 Price Changes : Last Change 2 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!

$5,995,000
Key Largo
Sunset Point   - MM: 95.00
4 Bed, 4 Baths, 1,872 SqFt Days Listed: 152
-2.52% ($155,000) 1 Price Change : 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 offering great investment potential. The choice is yours!

$5,999,000
Big Torch Key
Misc Big Torch Key   - MM: 28.00
4 Bed, 4 Baths, 4,315 SqFt Days Listed: 183
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!

$6,150,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 3,342 SqFt Days Listed: 26
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Historic Luxury Meets Modern Elegance in Old Town Key West!Step into a piece of Key West history with this remarkable home built in 1869 by Robert Watson, now completely reimagined as a luxury retreat while preserving its historic charm. Located on iconic lower Simonton Street, X Flood, this 6,608 sq ft sanctuary boasts 3,342 sq ft of living space with 5 en-suite bedrooms, including two primary suites, each with its own unique luxuries. The 1st-floor suite offers a jetted shower with chromotherapy lighting, while the 2nd-floor suite includes a private porch and soaking tub.This estate blends old-world craftsmanship with modern amenities, featuring a gourmet chefs kitchen with Viking, KitchenAid, and Bosch appliances, plus a separate dining room with a private porch--perfect for morning coffee. The spacious great room, with 20-foot retractable doors, opens directly to the outdoor oasis where youll find an 18,000-gallon saltwater pool with swim-up bar, waterfall, and color LED lighting, plus a separate spa for ultimate relaxation.The detached guest house with kitchenette is ideal for visitors or extended family. Entertain outdoors with the fully equipped outdoor kitchen and al-fresco dining areas surrounded by lush tropical landscaping for complete privacy.Historic touches, including restored windows, doors, and custom woodwork, blend seamlessly with modern upgrades like a whole-house Generac generator, hurricane shutters, and advanced smart-home technology--control everything from pool settings to security from your phone.With gated parking for 3 cars, EV charging station, and just steps from the best dining and entertainment in Key West, this estate offers the rare opportunity to own a piece of history while enjoying unparalleled luxury. Dont miss out on a home that offers everything youve been searching for, and more! Step into Luxury! For the Discerning Few: Arrange Your Exclusive Private Showing Today!

$6,250,000
Shark Key
Shark Key   - MM: 11.00
5 Bed, 5 Baths, 3,982 SqFt Days Listed: 23
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Discover a world of refined luxury and tranquility at 71 Cannon Royal Drive, an architectural masterpiece in the exclusive community of Shark Key. This meticulously maintained, 4,000-square-foot, custom-built home features 5 bedrooms and 4.5 bathrooms, embodying sophistication and island living at its finest. Sold turnkey, this property offers an unparalleled, ready-to-enjoy lifestyle.Set against breathtaking open water views, this residence is designed to impress. From the grand exterior that lights up beautifully at night to the spacious interiors featuring soaring ceilings and wall-to-wall windows. The main floor invites you into an expansive great room with glass doors that open to a veranda, seamlessly blending indoor and outdoor living. This flows effortlessly into the dining area, chefs kitchen, and multiple entertaining spaces. Expansive retractable windows in the kitchen open to an inviting outdoor sitting bar and dining area, creating a perfect flow for effortless entertaining and al fresco dining.The upstairs level reveals a luxurious primary suite with cathedral ceilings, a lavish bathroom, and a private terrace overlooking the water. An elevator connects all levels, adding convenience to this sophisticated layout.Additional features include a whole-house generator, integrated sound system, large pantry, wet bar, 2 laundry rooms, 2+ car garage, coffee bar, and balconies throughout.Outdoors, the home is a private oasis crafted for unforgettable gatherings. Set on half an acre, the property boasts exquisite landscaping that enhances its natural beauty. The outdoor storage spaces provide both convenience and functionality. With multiple lounging areas, an outdoor living room, and a stunning 50-foot lap pool, youll enjoy endless days and nights of entertainment and relaxation. Located just minutes from Key West, Shark Key has exclusive amenities that include a swimming lagoon, private beach, tennis and pickleball courts and a clubhouse.

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 11-26-2024.
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