luxury seaside houses for sale Islamorada, United States

Commanding 170 feet of private Florida Bay frontage and situated on over an acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors, providing vast screened porches both upstairs and down. The kitchen anchors the home with gorgeous views and a function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired amenities continue with a lagoon-style pool, putting green, and ample deep-water dockage with a boat lift, providing Bay to Ocean access in minutes via Channels 2 or 5. This offers effortless access to world-class boating and fishing. Just off the edge of the channel lies a rare bayside reef teeming with life and providing snorkeling right off your own dock. Located on the Lower Matecumbe island of Islamorada, Eagle Point balances modern coastal luxury with timeless island tranquility—an estate designed for those who seek both beauty and belonging by the water.

Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind gates on Plantation Key, this secluded retreat combines lush tropical landscaping with unmatched privacy for the ultimate island escape. The 8,988-square-foot main residence showcases exceptional craftsmanship and thoughtful design. One wing features a dramatic two-story primary suite with a private office, while the opposite wing includes four additional bedrooms and four bathrooms across two levels. A separate two-bedroom guest house provides extra space for visitors, and a whole-house generator adds convenience and peace of mind. Inside, custom woodwork, coffered ceilings, built-ins, and high-end finishes create a warm yet refined atmosphere. Amenities include a chef's kitchen, wine cellar, private gym, elevator, and seamless indoor-outdoor living spaces ideal for entertaining or relaxing by the water. Resort-style outdoor features include a custom pool, tiki bar, outdoor kitchen, beachside fire pit, putting green, observation pier, and a lighted tennis court with cabana. Convenient access by seaplane, helicopter, or a 90-minute drive from Miami makes travel effortless. Perfect for boating enthusiasts, the estate is near dockage and concierge dry storage options. Located in the heart of Islamorada, Palm Paradise offers easy access to world-class fishing, boating, dining, and the laid-back luxury of the Florida Keys. Offered at $26.4M, Palm Paradise is a rare opportunity to own a private waterfront compound ideal for luxury living, family retreats, or executive escapes.

Impeccably Designed Islamorada Waterfront Retreat! Welcome to your private island oasis! This stunning 3BR/3BA solid concrete waterfront home on Lower Matecumbe Key combines comfort and style with the ultimate Florida Keys lifestyle. Beautifully updated, this turnkey residence is move-in ready for immediate enjoyment. The inviting floor plan features a well-appointed kitchen with quartz countertops and stainless appliances with open living concept, a spacious primary en suite, and a versatile downstairs guest suite with bedroom and living area--perfect for hosting family and friends or creating your own private retreat. Situated on a canal with immediate ocean access, the property includes 75 feet of concrete dockage with boat lift for the boating enthusiast. The resort-style backyard is designed for endless entertaining with a heated pool, expansive sun deck, screened porch, and multiple indoor-outdoor living spaces--your personal vacation paradise. Located just minutes from Islamorada's acclaimed restaurants, local marinas, world-class fishing, and island attractions, this exceptional home offers the perfect balance of waterfront tranquility and vibrant Keys living. Whether you're lounging poolside, departing for a day on the water, or gathering with loved ones, every day feels like a getaway. Low Flood Insurance currently $2075 available to transfer.

Welcome to Casa Matecumbe, an extraordinary oceanfront sanctuary located at 74049 Overseas Highway in the prestigious Village of Islamorada. This iconic property represents one of the rarest opportunities in the Upper Keys: a private, gated, resort-style compound offering expansive open-water views, unmatched privacy, and the timeless charm of classic Florida Keys architecture. Set on a generous parcel with a sandy beach, and direct ocean access, Casa Matecumbe delivers the ultimate coastal lifestyle--one defined by serenity, natural beauty, and the freedom to enjoy the water at a moment's notice. The gated entrance supplies a perfect level of privacy. The approach sets the tone for the entire experience: peaceful, secluded, and authentically 'Old Florida,' yet elevated with the sophistication expected in a luxury Keys residence. Whether used as a full-time home, a seasonal retreat, or a legacy property to be enjoyed for generations, Casa Matecumbe offers a rare combination of location, land, and lifestyle that is nearly impossible to replicate. The main residence is thoughtfully positioned to maximize panoramic ocean views from nearly every room. Expansive windows and glass doors frame the turquoise water, inviting natural light to fill the interior spaces throughout the day. Upstairs there are 3 bedrooms and 2 baths as well as a gorgeous kitchen an open concept with dining under air conditioning or al fresco, Downstairs includes a large en-suite bedroom with water views as well as an additional kitchen and dining living area. Lower-Level Finished area of 1,065 is included in square footage. Both levels offer a breezy indoor-outdoor living--with modern comforts including updated finishes, impact windows, and spacious living areas. This 4-bedroom House is the perfect vacation home for larger families wishing to enjoy the pool, the beach and the ocean in a private setting.

Experience luxury waterfront living in the heart of the Florida Keys! 4 bedrooms and 2 bathrooms. This stunning modern home offers sleek finishes, breathtaking canal views, and direct boating access. Enjoy the spacious outdoor entertainment area, complete with a private dock, lush synthetic turf, and a large jacuzzi—perfect for relaxing under the stars. The upper-level terrace provides an ideal setting for lounging or hosting guests while enjoying the coastal breeze.

Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime waterfront location, this beautiful resort-style residence offers generous living spaces, including both upstairs and downstairs primary suites, three additional guest suites, a dedicated office, shaded porches on both levels and a spacious garage for ultimate flexibility. The gourmet kitchen flows seamlessly to a fully equipped outdoor kitchen and shaded lounge area—ideal for al fresco dining by the pool amid lush tropical landscaping. A rare combination of classic design, modern amenities, and timeless island charm. Effortless boating and space for all of your waterfront toys with 75' of deepwater dockage and quick access to both ocean and bay. Nearby homeowner’s park provides the added bonuses of a private, sandy beach and boat ramp. With the serene, wide canal views and cooling bay breezes, and this is where luxury, comfort, and natural beauty, convenience converge.

Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Caf, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and a rare tiki hut at the end of the dockyour new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living areaideal for guests or extended family. Whether you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

Welcome to Casa Mar Azul, a one-of-a-kind oceanfront estate located along the iconic Old Highway in Islamorada a rare offering with 200 feet of oceanfront shoreline, a private jetty with dockage, and breathtaking panoramic views of the Atlantic Ocean. This elegant coastal retreat blends indoor-outdoor living with an open floor plan and soaring vaulted tongue-and-groove ceilings that bring warmth and character to the airy living space. Floor to ceiling windows and doors lead to an expansive open terrace, where unobstructed ocean views take center stage and sea breezes invite total relaxation. Upstairs, you'll find two spacious bedrooms and two full baths, each thoughtfully designed for comfort and ease. A versatile bonus room opens to a covered lanai that leads directly to your own sandy beach the perfect spot for morning coffee or sunset gatherings. The private jetty stretches 200 feet into the turquoise waters and offers dockage at the end, ideal for boating, fishing, or simply soaking in the serenity of the sea. Nestled within mature tropical landscaping, this estate offers a sense of seclusion while being just steps or a short bike ride from Islamorada's best charming restaurants, local boutiques, and vibrant art galleries. Whether you're looking for a serene island escape or a place to entertain in style, this exceptional property captures the spirit of the Florida Keys with timeless charm and coastal elegance. Offered by appointment only your piece of paradise awaits.

Seize the rare opportunity to build your dream home in one of Islamorada's most coveted locations! This Ocean Front estate located directly across from the iconic Alligator Reef Lighthouse. Across the street from a protected preserve that will never be developed, and featuring a deep water channel capable of accommodating boats up to 40 feet, this property offers unmatched privacy and access.Imagine living just a short stroll from the legendary Square Grouper, Midway Cafe, Robbie's. Down the road from some of the best restaurants in Islamorada like Ziggie's, Mad Dog's, and Chef Michael's. This oversized lot, just shy of an acre, provides the perfect canvas for a builder, developer, or savvy end user to craft a stunning, custom-designed home in an unparalleled location.

Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. An existing legal nonconforming home with a waterfront swimming pool currently sits on the property and may be used as a residence or rental while architectural plans and permits are finalized, offering flexibility during the planning process. For buyers who understand the value of land in the Florida Keys, this offering represents something increasingly difficult to find: the opportunity to create a custom waterfront estate tailored entirely to your vision, rather than inheriting someone else's. A remarkable parcel for a remarkable build.

A rare architectural masterpiece by renowned architect Max Strang, this modern coastal estate in Port Antigua, Islamorada, redefines luxury waterfront living. Set on a private sandy beach, the residence offers 5 bedrooms, 6 full baths and 2 half baths across 6,367 SF of interior space and 10,483 total SF. Strangs signature tropical modernist design showcases natural materials, clean lines, and expansive glass walls framing panoramic ocean views. Amenities include a gym, golf simulator room, movie theater living area and a spectacular summer kitchen for entertaining. Outdoor living shines with a resort-style pool, spacious terraces and direct beach access. Every detail embodies refined elegance, relaxed sophistication and the timeless allure of Islamoradas coastal beauty. Fully furnished.

A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. Designed for elevated living, The Oasis blends resort-style amenities with the privacy and scale of a true Florida Keys compound. The grand porte-cochère entry sets the tone, leading to a single-level main residence with soaring ceilings, white oak floors, and 12' retractable glass walls that frame sweeping ocean views. The chef's kitchen is anchored by a Calacatta marble island, Thermador appliances, and a walk-in pantry, opening to a spacious great room and dining area ideal for entertaining. The main home features four bedrooms, six full bathrooms, and a soundproof theater room. The primary suite is a private retreat with a fireplace, dual walk-in closets, a safe room, and a spa-inspired bath with a steam shower. Each additional bedroom includes an en suite bath, private balcony, and ocean views. A detached guest house offers two additional bedrooms and bathrooms, creating a total of six bedrooms across the estate with endless space for expansion. The summer kitchen, alfresco dining areas, and multiple lounging terraces offer seamless indoor-outdoor living. The deepwater basin accommodates larger vessels and provides quick access to the Atlantic and Bay. Amenities rival a private resort: soundproof theater, fitness center with sauna, golf simulator, and two resort-style pools—each with a spa, sun deck, and outdoor entertaining spaces. Discreetly luxurious and effortlessly livable, The Oasis redefines waterfront living in the Florida Keys. Designed for ultimate security and safety, this home was built to provide unmatched peace of mind. Every element was designed with meticulous attention to detail and an uncompromising commitment to quality. The Oasis is not just a residence—it is a lifestyle statement in one of the Florida Keys' most desirable locations.

Introducing a newly completed architectural masterpiece overlooking the turquoise waters of the Atlantic Ocean in the prestigious enclave of Plantation Key. Set on over two private acres, this extraordinary estate embodies the pinnacle of coastal elegance, modern luxury, and serene island living. Spanning more than 9,000 sq. ft. of interior living space (15,000+ sq. ft. under roof), this expansive residence offers 5 spacious ensuite bedrooms, 5 full baths, and 3 half baths. Thoughtfully designed flex spaces include a fitness room, dedicated office, and state-of-the-art theater roomall of which can be converted into additional bedrooms if desired. The open-concept living areas showcase premium finishes throughout, elevated by Thermador and U-Line appliances, built-in ice makers, and a $200K upgraded package of commercial-grade CGI impact windows and doors for superior efficiency, storm protection, and enhanced style. Nearly every room captures sweeping ocean views, while over 1,735 sq. ft. of covered outdoor living spaces invite you to relax and entertain in the soothing coastal breeze. The resort-style grounds include a private pool and jacuzzi, complemented by an 80-foot dock with electric and water hookups, a 160-foot concrete jetty, and a 20,000 lb boat liftcreating an unmatched boating experience. Designed for ultimate convenience, the home features an elevator, dual laundry rooms (one on each level), a concrete shoreline retention wall, and a gated entry for privacy and an impressive sense of arrival. Zoned Residential Estate, the property is eligible for vacation rental licensing, offering exceptional potential for both personal enjoyment and investment return. Fully completed and move-in ready, this custom-built estate delivers world-class island livingwhere every moment is framed by endless blue water and unforgettable sunrises and sunsets.