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Lower Keys Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Total Listings 170
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$3,650,000
Big Pine Key
Piney Point Subdivision   - MM: 29.50
4 Bed, 4 Baths, 2,050 SqFt Days Listed: 214
-3.69% ($140,000) 1 Price Change : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Slip,Boa

Welcome to Tarpon Cove, an exclusive, resort-like retreat nestled on a sprawling estate lot in the heart of Big Pine Key. This recently renovated home offers a perfect blend of modern elegance and natural beauty, surrounded by the pristine flora and fauna of the Florida Key Deer Preserve. With four spacious bedrooms and three and a half bathrooms, this unique multi-level residence is designed for those who appreciate the finer things in life.As you approach the gated entrance, a long, driveway, shaded by mature native trees, leads you to this private oasis. The fully fenced yard offers complete privacy and is beautifully landscaped with tropical foliage. Designed with both luxury and durability in mind, this concrete home features a metal roof and impact-resistant windows and doors, ensuring peace of mind in any weather.Step inside to find an open-concept living space that flows effortlessly from room to room, all bathed in natural light and offering stunning views of the surrounding landscape. The modern kitchen is a chefs dream, complete with quartz countertops, a Samsung Bespoke appliance package, and a professional-grade gas cooktop. Whether youre entertaining guests or enjoying a quiet meal, the beauty of the Florida Keys is your constant companion, with breathtaking water views from almost every room in the house.Outdoors, the expansive dockage provides incredible boating access on the ocean side, with ample space for multiple boats. This property is a boaters paradise, offering direct access to the sparkling waters of the Atlantic. Additional amenities include RV hookup, covered parking, and garage storage, making this home as practical as it is beautiful.Tarpon Cove is not just a home--its a lifestyle. A rare and special property, it offers the tranquility and seclusion of a private resort, right in your own backyard. Discover the magic of the Florida Keys and make Tarpon Cove your ultimate escape.

$3,695,000
Big Torch Key
Misc Big Torch Key   - MM: 28.00
3 Bed, 3 Baths, 2,134 SqFt Days Listed: 44
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift300ft.

Tucked away on Big Torch Key, one of the Florida Keys best-kept secrets, this rare 3 acre luxurious custom estate offers the ultimate in privacy, tranquility and breathtaking waterfront views.With 357 feet of pristine shoreline on the Niles Channel and 180 views, this west-facing retreat is perfectly positioned for year-round sunset vistas. The design seamlessly connects over 4000 ft. of indoor and outdoor living, offering 2100 ft. of air-conditioned, light-filled interior and 2000 ft. of covered wrap-around screened-in porches. The elevated classically styled Key West Sea Captain architecture maximizes the view, allowing for ocean breezes and panoramas from nearly every room.The mid-century modern interior features an open concept design with floor-ceiling pocket slider doors to bring the outdoors in. The third floor master suite is a private sanctuary with a TV lounge, desk area, custom closets, and a spa-like ensuite bath with a soaking tub. Two additional bedrooms offer serene accommodations with custom built-in cabinetry while the homes three full bathrooms are elegantly appointed. The second floor opens to an additional 460-ft. shady patio while the third floor sundeck provides a private perch to take in the vast unobstructed views.Outside, the estate is also equipped for the active fisherman and boater featuring a 300-foot Lifetime dock with fiber grate decking and a 5,000-pound boat lift, floating swim platform, fish cleaning station and full dock utilities. Beyond the T-dock with its 4-foot draft, there is a 4-post boat slip allowing installation of a larger lift for bigger vessels. The Niles Channel affords quick access to both Gulf and Atlantic waters with 40-foot clearance at the Niles Channel bridge, while back country flats fishing is minutes away.A tiki bar, small beach and lush, tropical landscaping including many specimen trees (mahogany, gumbo limbo, blolly) and many species of palm ...(see documents for full description)

$3,945,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
4 Bed, 4 Baths, 3,817 SqFt Days Listed: 115
-17.80% ($854,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift150ft.Concr

Exquisite LUXURY Waterfront Estate in the exclusive Cudjoe Gardens. A STUNNING TURNKEY PARADISE, PRICE INCLUDES, 2 NEW HOBIE CAT KAYAKS, HIGH END DESIGNER FURNISHINGS & DECOR FROM RESTORATION HARDWARE, POTTERY BARN, AND MORE. This Custom Built Home is a masterpiece blending luxurious design with the serene beauty of the Florida Keys. Built on a sprawling waterfront elevated corner lot of 16,500sf with 260 ft of water frontage offering deep draft. This gorgeous property offers an unparalleled tropical lifestyle, perfect for those who demand the best in comfort and elegance.Property Highlights4 Bedrooms + Office/Studio: Spacious, sunlit rooms designed for relaxation and productivity, including a versatile office or creative studio space which could be a 5th Bedroom.4 Full Bathrooms: Impeccably designed with high-end fixtures and finishes.Gourmet Kitchen: A chefs dream, featuring state-of-the-art appliances, custom cabinetry, and expansive Quartz countertops ideal for entertaining.Imported Italian & Moroccan Flooring: Stunning, high-quality flooring that enhances the luxurious ambiance throughout.12-16 Ft Ceilings: Create an open, airy feel while showcasing architectural sophistication.Saltwater Pool: Dive into the generously sized, chilled & heated concrete pool with water feature, lights and lounging platformOutdoor Kitchen: Stainless Steel Appliances, Spacious layout, Perfect for entertaining.2 Boat Lifts, 20k and 10kAdditional Amenities3 A/C Units: Individually climate-controlled zones, including the 3-car garage for comfort and convenience.Full Property Generator, and 1000 gallon Propane Tank, Full Security System, Phantom SunShades for Screened in PorchThis meticulously designed property combines sophisticated interiors with exceptional outdoor living spaces. Located in a prime area of Cudjoe Key, this home offers privacy, stunning water views, and direct access to the pristine waters of the Lower Keys

$4,300,000
Key Haven
Key Haven 5th Add   - MM: 5.00
4 Bed, 4 Baths, 3,204 SqFt Days Listed: 106
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift60ft

This 4b/4.5ba luxurious home boasts Gulf of Mexico & deep canal waterfront living in Key West. It includes hurricane shutters, impact windows, metal roof with solar panels, and automated blinds. Ample parking with 2 large garages & driveway for 3 cars. 1st floor has a Chefs kitchen, a dining room perfect for hosting parties, a luxurious master suite with walk-in custom closets and the en-suite bath is a sanctuary of relaxation, with adjustable color lighting, his/hers vanity sinks on opposite walls, & full-size stacked washer/dryer with lots of storage. A half bath is also available for guests. Kitchen appliances include; induction cooktop with downdraft, D/W, Bev. cooler, convection wall oven & M/W, warming drawer & a fridge with TV. Abundant storage and appliance garages. Wood ceilings in the living room add to the charm, while the dining area has seating for 8 with a coffee/wine nook. On the 2nd floor, youll find 3 more bedrooms and a washer/dryer. One bedrm is a 2nd master with en-suite bath and large balcony overlooking the Gulf. Another bedrm is repurposed into a lounge, though it can easily be reverted back. This area shares access to a Jack n Jill bathroom equipped with his/hers sinks, connecting to the 4th bedroom featuring side-by-side closets and private porch overlooking the canal. Downstairs is an outdoor area, complete with a workshop and a full bath. Elevator runs from ground to 2nd floor. The kitchen has a sink, fridge, and gas grill. Also, an electric smoker and wood-burning pizza oven complete the outdoor cooking facilities. There are multiple gas grills. An outdoor TV swivels for viewing from the couch for 8, dining table for 6, the hot tub or a round table for 4. There is a splash pool w/ sail shade, a hot tub, shuffleboard, ping pong and outdoor wireless speakers. A private dock sits on the canal including 2 boat lifts with direct access to the Gulf and Atlantic. A fish cleaning station is on the dock, with water and electric.

$4,999,500
Big Pine Key
Pine Channel Estates   - MM: 29.50
4 Bed, 4 Baths, 2,812 SqFt Days Listed: 128
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.

$5,750,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
5 Bed, 5 Baths, 3,597 SqFt Days Listed: 163
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

$5,999,000
Key Haven
Key Haven 10th Add   - MM: 5.00
6 Bed, 6 Baths, 6,611 SqFt Days Listed: 181
-14.29% ($1,000,000) 4 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift200ft.

This Key Haven Estate rests on over 15,000 square feet of land with more than 260 linear feet of water access all while boasting over 6500 square feet of the finest living accommodations in the Florida Keys. The main Home has 5 Bedrooms and 4 and 1/2 bathrooms, the guest house has 3 bedrooms and 3 bathrooms. 39 Evergreen has the finest finishings all encased in 11 inches of solid concrete using insulated concrete forms and solid poured floors and stairs. Utilizing this type of Construction not only provides tremendous safety and privacy but allows for the impact glass windows and doors to be protected by hidden European style roll down shutters. The home has a vast 60 long pool with multiple levels, waterfalls and 6 seats to the swim up bar in the custom gazebo, perfect for entertaining, or when you are finished in the homes Private 400+ Square foot Gym. This home can accommodate over 9 vehicles in its 3800 Square Foot garage and has a Generator and Fire Suppression system for additional safety and security.

$6,895,000
Key West
Sunset Key   - MM: 0.00
4 Bed, 4 Baths, 2,558 SqFt Days Listed: 104
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Experience unparalleled island living on Sunset Key, an exclusive island community located in the heart of Key West Harbor. Accessible 24 hours a day via a dedicated island ferry, this extraordinary home offers the ultimate blend of privacy, luxury, and convenience. All this just a four minute boat ride from the vibrant streets of Key West.This bright and airy 4-bedroom residence is designed to capture breathtaking open ocean views. Large windows bathe the home in natural light, creating an inviting and serene atmosphere. The heart of the home is a fabulous chefs kitchen equipped with top-of-the-line appliances, perfect for creating culinary masterpieces while taking in the views of the sparkling water.Step outside to your beach-front oasis, where you can unwind and enjoy the gentle sea breeze or take in a spectacular sunset over the Gulf of Mexico. On the island, a wealth of world-class amenities awaits, including a gourmet restaurant, a rejuvenating spa, tennis courts, and more, ensuring your every need is met in this tropical paradise.With unparalleled luxury, exceptional views, and exclusive island living, this property offers the perfect retreat in one of the most sought-after destinations in the world.

$8,500,000
Key West
Filer Boyle Subdivision   - MM: 1.00
5 Bed, 5 Baths, 4,008 SqFt Days Listed: 269
-54.05% ($10,000,000) 1 Price Change : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

LUXURY AUCTION BIDDING OPEN! Bidding ends Monday, March 31st. Previously Listed $18,500,000. Current High Bid $8,500,000. Private Showings by Appointment.Experience unparalleled luxury at 400 South Street, the true Southernmost private residence in the Continental United States. This iconic Key West estate, winter home to esteemed American artist, the late Seward Johnson and his wife, seamlessly blends timeless elegance with modern amenities. The expansive 4,008-square-foot concrete home, situated on a generous lot plus almost one acre of bay bottom, offers five bedrooms and five and a half bathrooms. Upon entering, the formal living room evokes the charm of the Hemingway era, leading to a sunlit Florida room with sliding glass doors that open to a vast outdoor oasis. The primary suite and two guest bedrooms are accessible via an elevator, each opening to a large balcony that provides panoramic views of the Atlantic Ocean. The property boasts a magnificent 50 x 20-foot pool and ample lounging areas, perfect for enjoying ocean breezes and observing local birdlife. With its unique location adjacent to the iconic Southernmost Point buoy and proximity to Key Wests vibrant attractions, this estate offers an unparalleled living experience. Additionally, a coveted transient license allows for nightly rentals, presenting a prime investment opportunity or the option for a lavish private or corporate compound. Designated Multifamily (could accommodate up to 8 residential units) and located in the historic commercial tourist district, the possibilities are vast for a savvy investor. Part of the property needs complete renovation and the 1930 SF seawall requires partial restoration. THE Southernmost House is a rare gem in the United States! Due diligence package available upon bid registration.

$13,500,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
7 Bed, 7 Baths, 4,888 SqFt Days Listed: 50
+4.65% ($600,000) 1 Price Change : Last Change 15 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat LiftCut/

Welcome to Cypress Point, an exceptional and highly private, 7-Bed, 6-Bath, 4,888 Sq Ft oceanfront estate spanning almost a full acre on Cudjoe Key, where luxury and coastal beauty uniquely blend. This custom DAsign Source built home is privately nestled behind an electric gate and boasts the finest finishes and amenities which include an oceanfront pool, outdoor theater, 6-hole golf green, bocci ball and 7-car garage. The grand entry greets you with rough-cut coral flooring, 8-foot doors and an expansive Great Room, offering sweeping ocean views. The gourmet Kitchen is ideal for entertaining and features a Viking stove and microwave, refrigerator, two farm sinks, quartz countertops, ice maker, wine cooler, wet bar and beverage cooler. The adjacent Butlers Pantry is equipped with a SubZero refrigerator/freezer for your added convenience. A pop-up television allows viewing from both the Kitchen and Living Room. The dining area is further enhanced by the vast water views and Summer Kitchen ideal for table side grilling. The main level also features 2 Guest Suites with ensuites and a third 2-Bedroom Family Suite with a private veranda overlooking the Atlantic Ocean. The third floor showcases the luxurious Primary Suite, complete with endless ocean views, private balcony, drop-down screen projector, morning kitchen, walk-in closet and a spa-like ensuite which includes a massive shower, linen closet and drop-down mirror with a television. The fifth Guest Suite with its private balcony completes the third-floor layout. Boating and water enthusiasts will enjoy the deep draft dockage with both 40K and 17K boat lifts, two davits and 6K swim platform. Further enhancing this coastal estate is impact doors and windows throughout, electric blinds, whole-house generator, two 1,000-gallon propane tanks and laundry chutes for your added convenience. The breathtaking open-water views from every room showcase the illuminating sunrises and sunsets in this picturesque estate.

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 04-01-2025.
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