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 homes 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, its an experience.

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.

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Dont miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

Welcome to Bahia Bonita! This ultra-private bayfront estate in the heart of downtown Islamorada offers the ultimate combination of expansive open water views from every room plus deep-water dockage. If you have been wishing for an exceptional piece of Florida Keys paradise where natural beauty and luxury living meet storm resiliency, this solidly constructed, sustainably designed home may exceed your expectations. Begin your day by stepping out of your primary suite to your bayfront terrace and into an incomparable, second floor Infinity Edge pool. In the evening, slide open the wall of glass on the top floor to experience the brilliance of Islamoradas famous sunsets from your great room, gourmet kitchen or outdoor decks. Feel like grilling? Just one step away is an outdoor kitchen with bay view seating and adjacent dining. For stargazing, venture up the spiral stairs to the rooftop deck for a breathtaking front row seat. Built from solid concrete to withstand sustained 200 mph winds, this home also includes accordion shutters over impact glass for the ultimate defense against the elements. Outside, enjoy 250+ linear feet of open water frontage and a 100 dock with commercial-grade piles, composite decking and two boat lifts fitted with hurricane and storm surge protection. This unparalleled storm resiliency is combined with modern sustainability features including a large cistern with state-of-the-art water purification system, a grid-tied solar array and integrated Tesla Power Walls eliminating the need for a generator. Other functional luxuries built into the home are an elevator, professional camera/security system, central wet-dry vacuum system, mature landscaping and an enormous three-car garage, complete with workshop and storage. This home also boasts marble floors throughout and a spectacular floating staircase.This luxurious yet practical island estate is also within walking distance of many of Islamoradas favorite dining spots. Call today!

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost comfort. Located in a serene cove with a pristine natural beach, the home features floor-to-ceiling windows that offer stunning 180-degree panoramic views of the ocean. Every corner is meticulously designed with tasteful decor, exuding elegance while providing a personal, comfortable atmosphere. The property is in downtown Islamorada, Florida Keys, and includes a private beachfront terrace, a third-story private balcony, and a tranquil pool with a tiki hut, making it ideal for relaxation and entertaining. The outdoor spaces feature a cozy firepit, offering the perfect setting for intimate gatherings with the sound of the waves as a backdrop. As a vacation rental, this residence is a lucrative investment opportunity in a highly sought-after area. This home is a true masterpiece, offering unparalleled luxury, privacy, and breathtaking views.

The Villas at the Islands of Islamorada is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a twin room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.

The Villas at the Islands of Islamorada is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a twin room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.

The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a bunk room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.

This remarkable 32,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay.One of the key highlights of the lot is its exceptional dockage, which has previously accommodated a 36-foot boat, making it perfect for boating enthusiasts. The dock can be expanded to suit your needs, providing ample space for additional vessels or watercraft. The property also offers plenty of room for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds creating a tranquil atmosphere for evening relaxation.The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aqatic species like fish, birds, manatees and a mulitude of different birds. Zoned as Residential Estate, this property allows for weekly rentals, presenting an opportunity for investment or personal use. Its a perfect canvas for your dream residence or vacation retreat.With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this lot is one of the best properties on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation.Owner / Agent

Coconut Cottage beckons you to the quintessence of tropical living in Islamorada. This oceanfront haven boasts a 90ft sandy beach, a private boat basin, and an inviting waterfront pool, creating an idyllic backdrop for both relaxation and adventure. The main residence, featuring four bedrooms and three bathrooms, exudes vintage Florida elegance, complemented by a screened-in porch where one can savor the panoramic ocean vistas and gentle sea breezes. A Separate One-Bedroom, One-Bathroom Guest Cottage offers additional privacy and comfort, making it ideal for hosting friends or family. Constructed with durability in mind, both homes feature concrete walls and metal roofing, ensuring a sanctuary that stands the test of time. The propertys lush tropical landscaping and gated entry promise a secluded retreat, fully fenced to ensure your exclusive slice of paradise remains undisturbed. Ample parking accommodates a fleet of cars, boats, and trailers, while a dedicated storage shed keeps your water toys and fishing gear organized. Coconut Cottage isnt just a residence; its a lifestyle choice for those who dream of a natural tropical setting. Envision your special day at this perfect wedding venue, where a 7-day rental policy aligns seamlessly with celebrations and gatherings. With a charming boutique hotel nearby, your guests will enjoy the convenience and luxury that this unique property affords. Discover the rare gem that is Coconut Cottage, a treasure nestled in one of Islamoradas most sought-after locations, where every day feels like a blissful escape from the ordinary. Motivated Seller!

Welcome to this beautiful concrete home in the highly sought-after Venetian Shores subdivision in Islamorada! This beautifully remodeled 5-bedroom, 3-bathroom home offers a spacious, open living floor plan perfect for modern living and entertaining. Venetian Shores is renowned for its deep control depth and exceptional deep-water dockage. With 70 of dockage featuring TWO boat lifts--one 15K and one 20K--this home is a boaters dream.Step into the backyard oasis where youll find a sparkling pool with both heater and chiller, as well as an inviting tiki hut, ideal for relaxing or hosting friends and family. Enjoy quick and easy access to both the Atlantic Ocean and Florida Bay through the nearby Snake Creek Channel.This property is completely fenced for privacy, with two electric gates and meticulously landscaped grounds that offer outstanding curb appeal. Dont miss your chance to own a slice of paradise in the Florida Keys!

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today.Owner is Florida licensed real estate agent.

Discover Your Private Tropical Oasis in Islamorada.Welcome to your dream retreat in the heart of the Florida Keys in the sport fishing capital of the worldaa stunning Key West-style home nestled amidst lush greenery in an exclusive gated bayfront private club community. This residence is more than just a home; its a lifestyle defined by serenity, elegance, and the natural beauty of Islamorada.From the moment you pass through the palm-lined gated front entrance, you will notice the manicured tropical beauty of this community as you make your way to the classic architectural gem that will captivate you. Vibrant hues, large sitting porches, and timeless craftsmanship create a warm, inviting ambiance. Inside, open living spaces are bathed in natural light, blending seamlessly with the lush surroundings visible through every window.Step outside and find yourself in your very own tropical sanctuary. Towering palms, old growth trees, vibrant bougainvillea, and lush greenery surround the property, offering privacy and tranquility. Relax by the pool, host unforgettable gatherings on the expansive patio, or simply unwind as the breeze carries the scent of salt air.Nestled within a private club community, this home offers access to a range of world-class amenities, including a marina, sunset point, beach, and community pool. Plus, the vibrant culture and stunning waters of Islamorada are yours to explore from the protected marina.Whether youre seeking a permanent residence or a vacation escape, this property provides the perfect balance of seclusion and connection. From sunrise strolls on pristine beaches to evenings under the stars, every moment here feels like a slice of paradise.Dont just dream of the Keys, live it. Schedule your private tour today and experience firsthand what makes this home and private community so extraordinary.

Little Basin Key Lime Villa #3 is a beautifully appointed, 3 bedroom, 3.5 bath townhome with proven rental income. Nestled amongst a quaint row of rocking chair adorned porches, this residences design takes inspiration from Old Town Key West and features postcard views of sunset from deck and docks. The immaculate, tropically landscaped grounds lead to the shared dockage, pool, tiki hut, and cabana. Parrot fish and mangrove snapper swirl around the waterfront with room for boats up to 30 ft, and a floating dock for guest use. Located on Upper Matecumbe Key, Bayside, in the Heart of Islamorada, the compound is right next door to Library Beach and is situated within walking distance to the best local sunset venues in the American Caribbean. Watch Sunset Celebrations each day and Full Moon Parties each month from your private porch! Across, on the Oceanside of the island, The Morada Way Art Walk is every Third Thursday and many local boutiques, breweries and fine dining restaurants are within walking distance. The first floor is designed in an open concept with soaring ceilings featuring dining area, kitchen, half bath and guest bedroom with ensuite bathroom. Upstairs leads to two more bedrooms with ensuite bathroom, and the master bedroom features french doors leading to lovely covered porches. Fully furnished in immaculate white decor - come stay for a week .... or, forever! Boats up to 30 allowed at dock on a first come, first serve basis. Note: Easy to show! Agent must accompany.

Welcome to one of downtown Islamoradas most exclusive properties- a spacious estate thats hitting the market for the first time in generations. This ranch-style home sits proudly on four contiguous lots in the peaceful Grove Park Subdivision, offering something thats increasingly scarce in the Keys: space to breathe. With two bedrooms and an oversized garage (50 x 26) thats perfect for an artists studio, boat and car storage plus a Workshop, and Utility buildings. Space to park your RV or Camper. This property gives you room to live and create.Step outside and youll find yourself in a tropical paradise. Fruit trees dot the landscape, and carefully planned gardens create a private sanctuary. Lounge in your Gazebo and an in-ground pool (25 x 40) beckons on those warm Florida afternoons, while the lush landscaping ensures your privacy from the world beyond.Location? It doesnt get better than this. Take a short stroll and youre in the vibrant heart of Islamorada. Wander through Artists Alley, browse local shops, or treat yourself to dinner at some of the Keys finest restaurants - all just minutes from your front door.This property isnt just a home - its a blank canvas of possibilities in paradise. And with properties like this becoming increasingly rare in the Keys, it wont be available for long.

Your Slice of Paradise Awaits in Downtown IslamoradaDiscover the perfect blend of modern coastal living and convenience with this beautifully remodeled ground-level duplex in the heart of Islamorada. Located just a moment from the famous Cheeca Lodge and the vibrant Arts District, youll be surrounded by charming shops, restaurants, and galleries.Property Highlights: Two Separate Units PLUS a Guest Space: Each of the two dwellings is thoughtfully designed with a bright, airy ambiance to complement the island lifestyle. Use one unit for yourself and rent out the other, and/or welcome family and friends to visit! Durable Construction: Built with concrete and topped with a sturdy metal roof, this home is designed to withstand the elements. Impact windows and doors provide added protection and energy efficiency. Private Outdoor Oasis: The fully fenced yard features an electric gate, artificial turf for low maintenance, and lush landscaping with vibrant tropical foliage, perfect for relaxing or entertaining.Why Youll Love It:Whether youre looking for a permanent home or a vacation retreat, this property delivers the ideal Florida Keys lifestyle. The Village of Islamorada recognizes two dwelling units, adding significant value to the property.Dont miss your chance to own this coastal gem in an unbeatable location! Buyers should be able to convert this building in to one single-family home and transfer one of the building rights to another Village non-waterfront lot that is deemed appropriate by the Village. Two units are recognized by the Village. Buyers must confirm all with Village of Islamorada.

This newly remodeled 3 bedroom, 3 bathroom home is located on upper Matecumbe in the heart of Islamorada, Florida. The home features a unique layout with 1 bedroom and 1 bathroom downstairs, and 2 bedrooms and 2 bathrooms upstairs. The home boasts high-quality construction and modern finishes throughout. The open-concept living area is perfect for entertaining, with a spacious kitchen featuring stainless steel appliances and granite countertops. The bedrooms are all generously sized and offer plenty of natural light. Outside, the home features a large deck perfect for enjoying the beautiful Florida weather. The property is within proximity to world-class restaurants and is accessible to some of the best fishing and diving spots in the world. This home is the perfect blend of luxury and convenience, making it an ideal choice for those looking to experience the best that Islamorada has to offer.

Beautiful Downtown Islamorada Cottage! This newly constructed home is located on an oversized lot with a pool, outdoor entertaining area, plenty of storage, parking, and handicap access. The home features 3 bedrooms & 3 bathrooms with two of the bedrooms ensuite. The home offers a great floor plan and has been tastefully decorated with a beautiful kitchen including stainless steel appliances. This is a great investment with rental history. Dont miss the opportunity to own where you can walk and ride your bike to all the places downtown Islamorada has to offer including shopping, restaurants, bars, and all the amenities The Sports Fishing Capital of the World has to offer!

Paradise Found: Renovated Jungle Treehouse!Welcome to your dream retreat in the heart of the Florida Keys. Nestled in the highly sought-after village of Islamorada, this exquisitely remodeled 3-bedroom, 3-bath estate redefines luxury living- 2/2 up and legal nonconforming 1/1 down. Perfectly situated on a sprawling 15k+ square-foot lot (14k sf residential dry and 1k sf easement) , this property offers an unparalleled combination of elegance, privacy, and tropical charm. Concrete roof fully resurfaced in 2024, and electrical, and state-of-the-art impact windows, providing peace of mind and protection while letting in abundant natural light. The interiors have been meticulously updated whilst keeping the Old Florida Charm alive. The kitchen is a true chefs dream.

This stunning property offers a rare opportunity with two lots and over 24,000 square feet of space, situated in the heart of Islamorada. This property is one of the sixteen durable Red Cross homes constructed in Islamorada. Built with solid poured concrete, these homes are designed to withstand hurricanes. features ample room for EXPANSION, allowing you to customize the space to suit your needs and desires.This 2-bedroom, 1-bathroom home has been completely renovated in 2023 with modern upgrades. The bathroom features custom cabinetry and a walk-in shower with a glass enclosure. The updated kitchen includes stainless steel appliances--a propane range, microwave, dishwasher, and refrigerator--along with custom cabinets. Plus, the entire property is fully fenced, offering both privacy and security.The expansive outdoor space offers endless possibilities--whether you envision adding a pool, tennis court, or a beautiful garden, the choice is yours.Dont miss the chance to own a home where you can easily walk or bike to all the attractions downtown Islamorada has to offer, including shopping, restaurants, bars, farmers markets, and everything that makes The Sports Fishing Capital of the World so special!