luxury real estate for sale Islamorada, United States (page 2)

Start building immediately with this Waterfront TDR for use in the Village of Islamorada for a Single Family Residence on the water. Buyer has to verify with the Village if TDR is applicable to vacant lot. Buyer has to pay all closing costs associated with the transaction and the transfer fees to the Village. The Letter of Development Rights Determination from the Village is on file and can be provided upon request.

Make all of your Florida Keys fantasies come true at Fantasy Harbor! We're willing to bet you never even knew this gated community on Islamorada's Lower Matecumbe existed. This concrete harborfront home is being offered for the very first time. Upstairs 2 bedroom 2 bathrooms suites with open and spacious harborview living areas plus downstairs bedroom and bathroom with a bonus party hut reminiscent of relaxing Bahamian nights after a day on the water. Quiet & private living situated just off the Florida Bay in a protected harbor with 99' concrete seawall on cap rock plus boat lift. This one is a winner!

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly 4 acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the sparkling waters of the bay while lush gardens create a serene oasis. The home's architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. Spanning over 6,900 square feet, the interior is a seamless fusion of open-concept living spaces and private retreats. Soaring vaulted ceilings and vast windows invite abundant natural light and spectacular views of the bay, creating an indoor-outdoor flow. The primary suite serves as your personal sanctuary, complete with private terrace, spa-inspired bathroom, and walk-in closets fit for a connoisseur of fine living. Each guest has direct access to outdoor spaces and views. A bonus, versatile bunk room/media center sits just off the west wing of the home. The charming guest house is the perfect complement to the main home, nestled in its own secluded on site location this delightful addition exudes a warm, welcoming ambiance ideal for hosting guests, or as a private office or creative studio. This downtown Islamorada estate in an incomparable location; walking distance to shopping, dining, and local culture, also has appeal that extends to those with a passion for the great outdoors. Two protected docking basins and boat lift, sandy lounging beach, expansive outdoor lanai and outdoor kitchen offers the ideal space for entertaining or enjoying a quiet evening watching the sunset. Fly the seaplane in or land the helicopter. Premier boating access just moments away from the Intracoastal waterway and Ocean channels. Serenity Cay is not just a home, it's an experience.

Oceanfront acreage in the heart of Islamorada! Discover a unique opportunity to own oceanfront acreage right in the heart of Islamorada, the jewel of the Florida Keys. This remarkable property encompasses over 7 acres of pristine upland, complemented by bay bottom, and comes with a coveted building right, allowing you to create your dream estate. With an astonishing 700 feet of direct Atlantic beachfront, your oasis in paradise awaits. Nestled in the vibrant community of Upper Matecumbe Key, you have the canvas to craft your vision, with space for your main residence, a caretaker cottage, a detached guest house, a tennis court, and even a charming boardwalk leading to your very own private sandy beach. Not only does this piece of paradise offer unparalleled beauty and space, but it also boasts zoning that allows for weekly rental potential, making it a valuable investment. Seize the opportunity to make your waterfront dreams a reality in the Florida Keys. This is your chance to create a legacy estate that combines coastal luxury with the convenience of town living. Don't miss out on this once-in-a-lifetime opportunity!

Showcasing an oasis of distinguished elegance and prime coastal beach charm, this extraordinary property spans over 40,000 square feet of exquisite indoor and outdoor living spaces. It masterfully combines the sophistication of the Hamptons with the irresistible allure of the Florida Keys. Every detail has been meticulously crafted for discerning taste, from the shimmering mosaic fountains and grand staircases to the soaring floor-to-ceiling windows and bespoke art-stained glass elevator doors. An illuminated fireplace, intricate wrought iron balconies, and illuminated chandeliers add a timeless touch of glamour throughout the estate.Designed for both luxurious living and distinguished private events, the property features:

Nestled in the Safety Harbor enclave, Islamorada, this stunning Gulfside estate offers unparalleled blend of luxury and tranquility. Situated on a prime point w/open water and protected dockage, makes this a boater's paradise. With concrete seawall/2 boat lifts this home is appointed for waterfront living. Easy ocean access through Channel 5. Home features 8 ensuite BRs plus 2 half BAs. The master layout, a private sanctuary w/spa bath, showcases water views thru impact windows/sliding doors. Elevator ensures access to all levels; balconies invite you to savor unobstructed panoramas. The gourmet kitchen w/high-end appliances/gas cooktop is a chef's delight. With its seamless indoor-outdoor design and unmatched location, this property is the epitome of luxurious Keys living. Owner/Agent

Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boater's paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning station, this home is perfectly appointed for waterfront living. Easy ocean access through the nearby Channel 5 Bridge adds to its appeal for avid anglers and adventure seekers alike. Inside, the home features eight spacious bedrooms, each with its own ensuite bath, plus two additional half baths for convenience. The master suite is a private sanctuary with a spa-inspired bath, while the open layout showcases spectacular water views through impact windows and sliding glass doors. An elevator ensures effortless access to all levels, and the wraparound balcony invites you to savor unobstructed panoramas. The gourmet kitchen, complete with high-end stainless steel appliances and gas cooktop, is a chef's delight, complemented by an outdoor kitchen for alfresco entertaining. With its seamless indoor-outdoor design and unmatched location, this property is the epitome of luxurious Keys living. Owner/Agent

Completed in 2025 and positioned along one of the most coveted stretches of oceanfront in Islamorada, this extraordinary estate represents a once-in-a-generation opportunity to own one of the Florida Keys' most remarkable waterfront properties. Set on more than two acres of usable tropical grounds and directly overlooking the turquoise waters of the Atlantic Ocean, the estate offers an unrivaled combination of privacy, scale, and coastal luxury, redefining the very essence of oceanfront living. A gated entrance welcomes residents through lush tropical landscaping and a beautifully curated fruit orchard, creating a grand arrival experience that immediately conveys exclusivity, serenity, and sophistication. The property boasts approximately 210 feet of private sandy beachfront, a rare protected cove, and an impressive 230-foot private dock, providing exceptional access for boating, fishing, and an array of water-based activities synonymous with the Islamorada lifestyle. Designed to embrace seamless indoor-outdoor living, the residence offers approximately 7,500 square feet of refined interior space complemented by over 1,700 square feet of covered outdoor living areas, all carefully crafted to maximize breathtaking Atlantic Ocean views. The dramatic great room serves as the centerpiece of the home, featuring soaring 24-foot ceilings and expansive walls of glass that frame spectacular panoramic ocean vistas, creating an atmosphere of openness, elegance, and connection to the surrounding landscape. Expansive covered terraces provide the ideal setting for entertaining and relaxation, complete with a fully equipped summer kitchen, outdoor dining spaces, and sophisticated lounge areas overlooking the water. The gourmet chef's kitchen showcases premium Sub-Zero, Wolf, and Thermador appliances, combining exceptional functionality with refined design to satisfy the expectations of the most discerning culinary enthusiasts. Outside, a stunning 65-foot heated lagoon-style swimming pool anchors the resort-inspired grounds. A swim-up bar, luxurious lounge spaces, and a dedicated firepit gathering area create an extraordinary private retreat reminiscent of the world's finest luxury resorts. The residence further features two exceptional primary suites, offering remarkable flexibility for family living and guest accommodations while maintaining the highest levels of privacy and comfort. Additional amenities include a private orchid garden, a dedicated recreation and relaxation lounge, private elevator, integrated Sonos surround-sound system, impact-resistant windows and doors, durable standing-seam metal roof, double-height garage, dedicated water-sports equipment storage facility, and a whole-house backup generator. For buyers seeking even greater potential, an adjacent 0.7-acre parcel is available separately and includes development rights for an accessory structure with upper-level storage and additional facilities, providing a rare opportunity for future expansion. A truly iconic oceanfront trophy estate that captures the finest elements of luxury, privacy, and waterfront living in the Florida Keys, created for an international clientele seeking one of the region's most exceptional properties. Private showings and confidential information available exclusively upon qualified request.

Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architects Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.

Welcome to your coastal retreat in the highly sought-after Port Antigua neighborhood--where relaxed Keys living meets exceptional boating access and resort-style amenities. Residents enjoy a private homeowner's beach and boat ramp, enhancing the ease of life on the water. This solid CBS construction home offers approximately 75 feet of dockage, a 12,000 lb boat lift, and a convenient fish cleaning station--perfect for avid boaters and anglers alike. After a day on the water, unwind by the beautifully designed pool where a spa cascades into the water, complete with a swim jet, heater, and chiller for year-round enjoyment. Upstairs, the open floor plan is bright and inviting, anchored by a well-appointed kitchen featuring stainless steel appliances, quartz countertops, and a generous island ideal for gathering. Two spacious bedrooms and baths provide comfort and privacy, while a versatile Florida room serves perfectly as a home office and gym. Built for durability and peace of mind, the home includes a concrete roof, impact windows and doors, and an Arlo security system. A rooftop deck offers additional space to relax and take in the coastal surroundings. Downstairs, an expansive covered entertaining area flows seamlessly to the pool and tiki hut--thoughtfully equipped with lighting, ceiling fan, grill, side burner, sink, and refrigerator--creating the ultimate setting for outdoor living. Elevated above flood, the guest quarters feature a private living area, bedroom, and bath with access from both the pool and interior, making it ideal for visitors. A perfect blend of comfort, function, and island charm--this is Port Antigua living at its finest.

Positioned directly on the crystal-clear waters of the Atlantic Ocean, Château On The Ocean stands among the most extraordinary and private estates in the Florida Keys. Located within the exclusive enclave of Islamorada—often referred to as “The Hamptons of Miami”—this remarkable property redefines luxury oceanfront living through an unparalleled combination of architecture, scale, privacy, and lifestyle. Completely reimagined and rebuilt in 2023, the estate is the result of a visionary approach blending contemporary design, advanced engineering, and world-class craftsmanship. Set on nearly two acres of pristine private oceanfront, the property offers more than 19,700 square feet of total living and entertainment space, including over 10,000 square feet of climate-controlled interiors. From the moment of arrival, the estate conveys a profound sense of exclusivity, architectural presence, and coastal sophistication. Interior features include: soaring ceilings dramatic floor-to-ceiling glass walls breathtaking Atlantic Ocean views couture-level finishes seamless indoor-outdoor living environments Designed to rival the world’s finest private resorts, the residence offers an extraordinary collection of lifestyle amenities. Wellness & Recreation professional fitness center indoor basketball and pickleball court private putting green custom-designed glamour suite dedicated wellness and relaxation spaces Entertainment Collection Baccarat-inspired grand ballroom outdoor cinema with a 300-inch LED screen panoramic rooftop terrace expansive event and entertaining areas Outdoor living is equally impressive, featuring: mosaic-tiled resort-style swimming pool oceanfront spa outdoor dining pavilion waterfront fire-pit lounge multiple terraces overlooking the Atlantic Ocean spectacular coastal and open-water views For boating enthusiasts, the estate includes: private 100-foot dock direct Atlantic Ocean access infrastructure suitable for large yachts and watercraft An exceptionally rare opportunity is presented through approved expansion plans that allow for: 6 additional luxury suites 2 additional oceanfront residences development into a world-class multi-structure private compound More than a residence, Château On The Ocean is a legacy estate designed for a global clientele seeking one of the most significant oceanfront properties available anywhere in the United States. Contact us for confidential information or to arrange a private presentation of this exceptional estate.

Venetian Shores Has It All! Welcome to your slice of paradise in the heart of Islamorada's most sought-after boating community. This beautiful 4 bedroom, 3 bath coastal retreat is designed for both relaxation and entertainment, featuring 70 feet of deep-water dockage along a 100-foot wide canal - just seconds from open water via Snake Creek. Step inside the front door to access the elevator and interior stairs. Upstairs, the main living area offers 2 bedrooms and 2 baths, a wide open floor plan, and a gourmet kitchen with a large center island, granite countertops, stainless steel appliances, and a dedicated workstation. Enjoy sunset cocktails from the screened canal-side terrace, accessed via impact-rated sliding glass doors. Downstairs, the ground level is a haven for guests and fun - featuring a pool table, a comfortable tv area, 2 more bedrooms and a full bath, laundry room, and garage for all your gear. The backyard is pure Keys magic - complete with a heated pool, tiki hut, hot tub and an expansive deck for sunbathing or relaxing in the shade. Boaters will love the 70 ft concrete dock with a 15,000 lb boat lift, 50 amp shore power and fish cleaning station. This home checks every box for the ultimate island lifestyle - whether you're heading east to the Atlantic or west to Florida Bay's backcountry to enjoy fishing and breathtaking sunsets. Live the dream in Venetian Shores - where the boating is easy and the living is even better.

Coastal elegance meets the ultimate boating lifestyle in this beautifully updated Venetian Shores home. Designed for effortless Keys living, the open floor plan is filled with natural light, highlighted by a dramatic floor-to-ceiling wall of windows in the living area that brings the outdoors in. An inviting entrance foyer welcomes you inside, with interior stairs to the main living level. The spacious kitchen is the heart of the home, featuring stainless steel appliances, a large island for gathering, and a separate laundry room and pantry for added convenience. The main living level offers two guest bedrooms and two full baths, including one bedroom with a private en-suite bath. Direct access from the second-floor living area to the pool deck creates a seamless connection between indoor and outdoor living. The open floor plan offers plenty of room for dining, watching TV, conversation and even some ping pong. Upstairs, the expansive primary suite provides a peaceful retreat with a walk-in closet and luxurious en-suite bath. A fourth bedroom on the third floor offers flexibility for guests, family, or a home office. Separate air-conditioning systems for each floor ensure year-round comfort. Outside, 70 feet of dockage and a 27,000-pound boat lift make this property a dream for boating enthusiasts, with quick access to both the Atlantic Ocean and Florida Bay. The resort-style backyard is ready for endless summer fun, featuring a sparkling pool, expansive sun deck, shady lounging area, and abundant storage for all your fishing, diving, and water sports gear. Whether you're entertaining friends, heading out for a day on the water, or simply relaxing poolside, this exceptional Venetian Shores home offers the perfect blend of coastal sophistication and waterfront adventure.

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. The 2/2 pool home is updated and ready for refined living.

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.

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 this exquisitely designed home located in beautiful Port Antigua. This is an entertainer's delight featuring marble flooring throughout the home. It boasts 2 full kitchens, one of which is outdoors so you can bring your fresh catch in from the boat and start cooking immediately while the smell of night blooming jasmine envelops you. There is a fully fenced in yard for your furry friends. You'll have a 65 foot dock for your boat to spend days on the crystal clear blue waters that surround our beautiful islands. This home has 3 bedrooms and 3 1/2 baths, a beautiful indoor bar with the ability to add another shower in the downstairs half bathroom. You'll be proud to call this house home.

Dream location in Port Antigua! This property is a GEM with a 75 ft. wide lot on the main waterway with no houses across the water. Upstairs you'll enjoy an open floor plan with 2 sets of 8 ft. sliding glass doors that pocket outside the walls for access to the screened lanai. The pitched concrete roof adds volume to the living area and primary bedroom. On the ground level there is a permitted bath and a large workshop and car port with very high ceilings. The waterfront features a dock with a tiki hut for shade and a 16,000 lb. 4 post boatlift. There is plenty of room for a pool in the backyard. Buy this GEM and polish it into a brilliant diamond!