Florida Keys Homes For Sale on the Ocean Side of the Island. Oceanfront Homes

Welcome to Cypress Point, an exceptional and highly private oceanfront estate on almost 1 acre on Cudjoe Key, where luxury and coastal beauty seamlessly blend. Behind a private electric gate, this 7-Bedroom, 6-Bath home, designed by Design Source, boasts the finest finishes and a wealth of amenities, including an oceanfront Pool, outdoor Theater, 6-hole Golf Green, Bocci Ball and a 7-car Garage--each detail crafted for ultimate enjoyment. Upon entering, youre greeted by rough-cut coral flooring, 8-foot doors, and an expansive Great Room that offers sweeping ocean views. The gourmet Kitchen is perfect for entertaining, featuring a Viking stove and microwave, refrigerator drawers, two farm sinks, quartz countertops, an ice maker, wine cooler, wet bar, and beverage cooler with Subzero refrigerator & freezer in the adjacent Butlers Pantry. A pop-up TV allows for both Kitchen and Living Room viewing. The dining area is enhanced with wide water views and summer kitchen for table side gilling. Also on the main level youll find 3 ensuite Guest Suites, 2 with gorgeous ocean views plus a 2 Bedroom Family Suite with Bath and veranda. The third floor showcases the luxurious Primary Suite, complete with endless ocean views, a private balcony, drop-down screen projector, morning kitchen, walk-in closet, and a spa-like ensuite with a massive shower, linen closet, and a drop down mirror with TV offering stunning ocean views or your favorite morning show. A 5th Guest Suite with a private balcony completes this level.For boating enthusiasts, the estate offers deep draft dockage with a 40K and 17K boat lift, two davits, and a 6K lb swim platform. Enjoy breathtaking views of the sunrise and sunset over the open ocean, channel, and canal. This stunning retreat is equipped with impact doors and windows, electric blinds, a whole-house generator, two 1,000-gallon propane tanks and laundry chutes. Built-in speakers throughout the property ensure an unforgettable ambiance.

Nestled within the confines of exclusive Plantation Island, at the end of a quiet cul-de-sac, lies a monumental Oceanfront estate of unparalleled proportion. Enveloped in lush tropical landscaping, and sprawling across an oversized 17,900 Sq. Ft. Point Lot, boasting stunning Open Water Views, every detail has been considered at this coastal retreat in coveted Hawks Cay! Enjoy Direct Ocean Access with approximately 200 of concrete seawall, with additional dock featuring jetski and boat lifts, this exceptional property allows for frequent boating with ease. Cool off in the resort-style, saltwater infinity pool, or sink into a luxurious hot tub at days end while taking in stunning Sunset Views. Venture inside this colossal masterpiece through a sleek, glass elevator. The show-stopping Great Room features soaring ceilings, well-appointed wet bar, and walls of impact-resistant doors and windows which open to unobstructed Ocean Views. Ideal for entertaining, the open-concept main living space flows seamlessly into an expertly-equipped Chefs Kitchen, complete with premium JennAir appliances, ample prep- and storage space, and generous peninsula with counter seating. Guests will enjoy elevated accommodations in a separate wing, with elegant en suite bathrooms, and access to a spacious veranda overlooking the well-manicured yard and Open Ocean beyond. The primary suite epitomizes luxury, boasting an expansive walk-in closet with custom built-in storage, opulent en suite bathroom, with Ocean Views, deep soaking tub, walk-in shower adorned with walls of onyx stone, and veranda access. The primary bedroom features impact-resistant, pocket sliding glass along two walls, which open entirely for enjoying sublime sunsets and ocean breezes; relax and unwind in this exceptional retreat. The property offers a plethora of parking and storage with detached garage, open- and street parking. Peace and tranquility abound at this extraordinary property!

Aptly named The Sanctuary Islet, this rare, secluded peninsula is a hidden gem within a protected 25-acre private preserve of native trees and mangroves in scenic Key Largo-- the first island of the Florida Keys. Privacy is a key feature of this property, offering breathtaking views, lush tropical vegetation and daily visits from exotic birds. Enjoy year-round sunrises over the Atlantic from this truly unique retreat.Surrounded by pristine ocean yet walking distance to restaurants, bars, etc. this resort-like estate provides an experience comparable to a private island--but with all the conveniences of mainland living. Behind two private entry gates, this estate offers what is likely the most secluded and private setting in all of the Florida Keys.The 4,000 sq. ft. main home features 2,000 sq. ft. of balconies plus 4,000 sq. ft. of additional space downstairs. With four spacious bedrooms, including luxurious ensuite bathrooms, this home is designed for ultimate comfort and convenience. The indoor-outdoor tropical bathrooms add a touch of luxury, blending sophistication with nature. The seamless integration of indoor and outdoor living spaces immerses you in the lush surroundings, with ample space for al fresco dining, lounging, and entertaining.Pre-approved plans for a 3-bedroom, 3-bath guest house are included. As featured in The Wall Street Journals Global Mansions, this estate was designed by a world-renowned architect-engineer team and built to withstand direct-impact Category 5 storms.For boating enthusiasts, navigate your vessel into your own protected boat slip, accommodating a 45 boat on a 24,000-pound lift, with an expansive turning radius and direct access to a wide-open turning basin--no fairway maneuvers required.Whether you plan to make this your primary residence or an investment property, this turnkey home comes with a great management team in place. Opportunity to unite with an adjacent property, creating your won compound.

Discover the essence of elegance at Southern Paradise, a coastal masterpiece nestled along the Atlantic Ocean. Located at Mile Marker 83, this property offers direct Old Road access, perfect for walking, biking, or carting. With over 200 ft of beachfront on 1.5 acres, the main residence boasts sunny verandas, 5 bedrooms, 6.5 baths, and more than 5,600 sq ft of air-conditioned living space. A separate guest cottage provides an additional 2 bedrooms and 2 baths, ideal for visitors seeking comfort and privacy. A paved old brick driveway leads up to both entrances and garage. From the moment you step into the inviting french door entrance your eyes are fixated on blue sky, beach and water. The 1st floor living space opens to a cool, grassy lanai, leading to the beach, a lap pool, and a hot tub. Spacious patios offer ample room for guests to savor the Caribbean breezes, while the pier, skiff lift, and kayak launch provide easy ocean access. The main residence is designed for entertaining, featuring expansive ceilings and a layout that includes both an East and a newly added West wing. Each generously appointed bedroom comes with its own ensuite bath, ensuring ultimate comfort and privacy for family and guests. On the 1st floor, East-facing french doors open to over 1,900 sq ft of covered terrace. The open-concept great room encompasses a kitchen equipped with a Wolf gas range, double SubZero refrigeration, and an attached wine cellar, all centered around an expansive island counter. A wet bar and powder room adjoin the kitchen, enhancing convenience for gatherings. The West wing includes an exercise room with a full ensuite spa bath and a luxurious primary suite. The master bath features an ocean-view soaking tub, double vanities, a separate shower, bidet, and water closet.This wing also offers a well-equipped laundry room, storage cabinetry, an office alcove, and direct garage access. 2nd floor presents 2 guest rooms that share a sitting room, wet bar, & terrace.

Garden Coves Southern Diversion is a peaceful and private North Key Largo escape, conveniently located right off John Pennekamp State Park and just a stones throw from Ocean Reef and quick ride to South Miami. Gorgeous open water view throughout the spacious home, plus over 350 of waterfront; excellent boating location just south of Jewfish Creek Bridge for fast Ocean to Bay access. Multiple nearby fishing and dining destinations make this property all the more desirable. Protected 30 and 70 docks on the inside canal for your island living toys. The home is being offered together with additional back lot and plans for guest home, both mixed use zoned parcels allow for wedding venue and vacation rentals or to host an abundance of events and guests. Current rental income available upon request.

Nestled in the panoramic setting of Islamorada, Florida, the brand new construction at 87895 Old Hwy offers a premium blend of luxury, privacy, and elegant island living. Sprawled over two acres on the azure Atlantic, this opulent abode stretches a massive 9,011 sq ft under air, extending to over 15,000 sq ft under roof. The expansive property includes five spacious bedrooms, five state-of-the-art baths, along with three additional half baths. The home features Thermador /Uline appliances including ice makers & upgraded eco-insulated commercial CGI windows and doors, an additional investment of $200k over the original allowance, that enhance the comfort and luxury of the interiors. Experience unmatched waterfront vistas with the houses 160 ft concrete jetty wrapped in a retaining wall and an 80 ft dock with electric and water facilities. Preserve your luxury vessels on the 20k 4 post elevator lift, adding convenience to lifestyle. The residence also includes an exercise room w/ possible conversion to 6th bedroom, theater room w/ possible conversion to 7th bedroom , office/den, & a laundry room on each level. An elevator ensures smooth movement across the floors. Indulge in outdoor living with the private pool, jacuzzi & around 1735 sqft of porches for lavish entertainment & serene lounging.The property comes protected by a concrete retention wall along the entire perimeter of the shoreline, ensuring complete tranquility. A private gated entrance exudes grandeur while providing security. This estate is zoned (Residential Estate), allowing the owner to apply for vacation rentals, if desired. Currently under construction, the property is perfect for those seeking a custom luxury experience. Enjoy a world-class island living experience in this architecturally significant estate filled with premium luxuries nestled right on the turquoise-blue waters of the Atlantic. Agents please check agent remarks

Welcome to 16 Seaside. This is your opportunity to have it all at your truly rare, ocean front, protected lagoon, new construction, Key Largo dream entertainment and relaxation haven. Imagine looking out past your outdoor pool and entertainment suite, across your private lagoon, past your tiki hut on your private beach to your view of the Atlantic Ocean. Outside you have 7 balconies, resort quality pool and covered entertainment oasis, private lagoon with parking for up to six boats each with their own shore power and water, private beach with tiki hut, privacy fences, automatic gate and approximately 2,500 square feet of covered parking. Inside you have all the amenities of a modern, newly constructed luxury home. You will have 6,585 square feet under air with state-of-the-art, comprehensive, fully integrated smart home which include full home lighting, climate control, audio and security, as well as outdoor control of the pool and outdoor lighting, multilevel entertainment options, stunning ocean views, 7 bedrooms with a primary on each floor, 7 full in-suite bathrooms, 2 half baths, multi floor laundry rooms, walk in and climate-controlled showpiece wine cellar, exquisitely appointed custom made kitchen, three level elevator, 4 zone cooling, and a whole home back-up generator. Located in Key Largo, this spectacular home is only an hour drive to Miami offering easy travel, big city entertainment and dining while allowing a quick escape back to the tranquility of your seaside oasis. Enjoy world class fishing and boating with room for all your friends, their boats and all the water toys. Suburban/commercial zoning is investor and 1031 exchange friendly. 16 Seaside is currently under construction and delivery is scheduled for January, 2025. Call today to make sure delivery is to you.***Note: This is a double lot with total lot size of 21,250 sq ft.

Nestled along the sun-kissed shores of exclusive 15th Circle on prestigious Key Colony Beach is the iconic Lighthouse. This expansive and recently updated home offers the epitome of luxury coastal living. With its private beachfront, youll wake up to the gentle lull of the waves and breathtaking views of the Atlantic Ocean. Relaxation meets sophistication. This spacious residence boasts:Generously sized living spaces designed for comfort and coastal elegance married with an open concept capsulating the tranquil Atlantic Ocean views.Upgraded kitchen equipped with modern appliances, perfect for culinary enthusiasts and entertainers alike.9 stylish bedrooms, each offering serene views and ample natural lightImpeccably renovated bathrooms with premium fixtures and finishesOwners quarters for unparalleled privacy and comfort boasting an Owners Suite that coastal living dreams are made of, complete with a generous walk-in closet, steam shower, tub, double vanity with storage galore, a separate living space with wet bar, pilates and music studio overlooking the ocean, beautiful home office and so much more. Private beachfront, one of a kind sparkling oceanfront pool for refreshing dips and lazy afternoons under the sun20k lb boat lift and private mooring ball granting seamless access to the crystal-clear watersOutdoor spaces ideal for entertaining, from intimate gatherings to lavish partiesWhether you seek a serene retreat or an entertainers dream, this Key Colony Beach gem offers the ideal canvas to live your coastal dream. Experience the allure of Florida living in this luxurious waterfront haven. Embrace the serenity of oceanfront luxury living.

Experience the ultimate in luxury and design at this custom-built masterpiece on a private peninsula along the coveted Adams Cut Waterway. This 4-bedroom, 7-bathroom estate spans 4,000 square feet and offers breathtaking open water views, unmatched privacy, and world-class amenities. From the triple-poured concrete roof to La Finesta impact windows, every detail of this fortress is built to the highest standards. Enter through the curved travertine staircase with underlighting and custom water feature. The main living area features floor-to-ceiling windows, a Nexus TV that descends from the ceiling by remote, and a wet bar with an ice maker and storage. The chefs kitchen is an artistic showpiece, complete with a backlit quartzite waterfall island, soft-close cabinets, a built-in wine cooler, and high-end appliances. The private top-floor primary suite offers a spa-like atmosphere with panoramic views. A bonus room on the same level adds versatility, perfect as an office, gym, or library. And a rooftop infinity pool featuring a swim-up bar, ambient lighting, and water features, creating a resort-style oasis. The ground level is designed for entertaining with a summer kitchen, Lynx grill, salt-chlorinated pool, and teak-clad ceilings. A turf yard and paver driveway adds style and functionality. This home is fully equipped with a whole-house generator, elevator, custom closets, remote controlled shades, and an advanced security system with remote access. A stocked 100-bottle wine cellar, ample dockage, a 20x8-foot swimming platform, and so much more. This estate is more than a home--its a lifestyle. Dont miss the opportunity to experience this extraordinary Key Largo retreat.

3 HOMES, OVER 100 PROTECTED DOCKAGE & OVER 550 NATURAL OCEANFRONT BEACH ~Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. Now being offered for the very first time, this one of a kind legacy property beckons you to bask in original elements of the Florida Keys way of life at Kids Cay. Three charming homes; a timeless 4 bedroom main house plus 4 bedroom guest house and a lovely 2 bedroom caretakers cottage. This tropical and tranquil estate offers ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes. Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals. This offering is for the south side (over 4 acres upland plus ocean bottom parcel) of property and over 550 of beachfront. See MLS#604054 for entire offering.

LUXURY PROPERTY AUCTION: BID 21-31 MARCH. Listed for $18.5M. Starting Bids Expected Between $5M-$8M.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 9 residential units) and located in the historic commercial tourist district, the possibilities are vast for a savvy investor. THE Southernmost House is a rare gem in the United States!

Tranquility Haven features the newest construction in Islamorada... completed January 2025! As you enter the gated and fenced sanctuary a long winding driveway leads up to an elevated entrance and convenient 1st floor living access. The 6 bedrooms and 9 bathrooms provide the epitome of coastal living with uninterrupted views of the turquoise waters on the Atlantic Ocean, with serene sunrises, and the gentle symphony of waves as your daily backdrop. Nestled on 210 of private sandy beach, this 2.04ac +/- serene oasis invites you to indulge in 6,946 sf of air-conditioned elegance and 1,800 sf of covered outdoor living designed for relaxation and entertaining. At its heart, a stunning 65 blue lagoon pool with swim-up bar stools, propane fire pit and spacious lounging patio promises unforgettable moments with family and friends.Inside, every detail reflects the designers mastery, from the chefs kitchen with SubZero, Thermador, and Wolf appliances to the grand living spaces that blend sophistication with comfort. The residence boasts 2 master suites that include double bathrooms and closets! A luxurious feature of the 1st floor master suite is a shower al fresco surrounded by a unique orchid garden and immediate access to the spa and pool patio. The 2nd floor master suite ensures more privacy and the ultimate sunrise horizon view! Much more is revealed as you walk from room to room - a flex room provides for possibilities of fitness, office or guests. A family room designed with home theater technology, a 2 car garage together with a beach-access garage and professionally landscaped grounds is complete with a tropical fruit orchard! Begin each day with golden sunrises and end with starlit skies, all within the embrace of an ocean breeze. Encounter warm Winter days and cool Summer nights. Whether hosting lavish gatherings or seeking peaceful solitude, this estate can be your haven - a perpetual island vacation in the Florida Keys!

Discover the crown jewel of the Florida Keys.This extraordinary five-acre oceanfront estate redefines luxury, offering 244 feet of private ocean frontage and unmatched tropical serenity. From the moment you pass through the gated entrance, youll be immersed in a world of elegance, privacy, and unparalleled amenities.A timeless Chicago brick-paved driveway winds gracefully along the lush rain forest and fruit orchard, leading through the grand Palm Alley to the heart of the estate, setting the tone for the tropical oasis that awaits.The custom-designed 5,600+/- sq. ft. main residence by DAsign Source showcases architectural brilliance and exquisite craftsmanship. A separate 2,999 sq. ft. guest house includes its own kitchen, multiple bathrooms, workshop, and spacious living areas, making it ideal for hosting guests or staff.The resort-style pool features waterfalls, waterslide, a Tahitian-style river, an expansive spa, a swim-up tiki bar, and a tiki village. Private bedroom balconies provide direct access to this stunning pool, making it perfect for tranquil escapes and lavish entertaining.Boating enthusiasts will love the private marina, boat ramp, and charming bait shack, offering instant access to the world-famous waters of the Keys for fishing, diving, and boating adventures.Inside, the estate is designed to impress, featuring a gourmet kitchen, opulent guest suites with private balconies to the pool, and a luxurious movie theater. The primary en-suite dazzles with a spa-like sanctuary, ensuring every moment here is extraordinary.Beyond the elegance, this estate is built for durability, with impact-resistant windows and doors, generator, and cistern. Outside, enjoy expansive porches, multiple garages, a barn, and a tortoise habitat . With potential for a private hangar, this property offers unmatched exclusivity.Experience the pinnacle of Florida Keys living--where luxury, tranquility, warmth and prestige come together in perfect harmony.

Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. Now being offered for the very first time, this one of a kind legacy property beckons you to bask in original elements of the Florida Keys way of life at Kids Cay. Three charming homes; a timeless 4 bedroom main house, separate 4 bedroom guest house and a lovely 2 bedroom caretakers cottage. This tropical and tranquil estate has nearly 8.5 acres of upland plus 7.98 acres of ocean bottom plus ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes. Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals. Also being offered with south side only for $17m see listing #613236.

An exquisite masterpiece of coastal luxury crafted by visionaries to create the ultimate secluded paradise. This architectural gem, designed by the renowned Siskind architects Bruce Carlson and Steve Siskind, offers an extraordinary lifestyle in an over five-acre waterfront oasis. Raymond Jungles landscape mastery frames the canvas, while Sam Robins interior magic awaits within. Experience approximately 11,000 sq ft of air-conditioned, carefully curated living space that is meticulously crafted with attention to detail. The gross square footage exceeds 17,895 sq ft, including covered outdoor verandas that seamlessly blend indoor and outdoor living. A four-bay air-conditioned collectors car garage awaits your prized vehicles. Additional covered parking porticos and a crushed shell driveway bordered by cut coral provide ample space for guests. Step into a world of tranquility with a private saltwater pond teeming with native sea life. Wander along the stone-through path for an intimate encounter with nature and carefully curated specimens. Situated on a peninsula, this estate offers complete privacy and security. A secluded beach area invites you to dip your toes into the ocean without prying eyes. Hosting soirees on the peninsula grassy area could serve as a helipad with a tiki lounge. Resort-style amenities include a gas-heated oasis pool, hot tub, and waterfall grotto to create a tropical paradise. Built-in swim-jet therapy and a beach entrance enhance your relaxation. Gas-powered tiki torches illuminate the evenings. Thoughtful details throughout, with an air-conditioned equipment room and cabana bathroom, add convenience. The elevated, fully equipped summer kitchen features a push-button elevated TV and a pizza oven, all with unobstructed views. A 450-foot dock with two boat lifts and a private protected boat basin awaits your vessels. This is more than a home; its an unparalleled legacy of luxury and privacy waiting to be claimed.