Upper Matecumbe Key Islamorada Florida homes for sale starting at Fifty Thousand Dollars

$25,000,000 - Upper Matecumbe Key Islamorada, FL

82768 Overseas Highway Upper Matecumbe Key Islamorada, FL - 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.

$9,950,000 - Upper Matecumbe Key Islamorada, FL

82238 Overseas Highway Upper Matecumbe Key Islamorada, FL - 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. Don't miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

$6,750,000 - Upper Matecumbe Key Islamorada, FL

83407 Old Highway Upper Matecumbe Key Islamorada, FL - 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.

$6,600,000 - Upper Matecumbe Key Islamorada, FL

100 List Street Upper Matecumbe Key Islamorada, FL - Built in 2014, Bahia Bonita is an ultra-private, luxury bayfront estate found in the heart of Islamorada. Situated on a peninsular parcel with 250+ linear feet of open water frontage of crystal-clear water teeming with marine life, this home is within walking distance of Islamorada's favorite dining spots. Designed to offer the ultimate combination of location, deep-water dockage, storm resiliency and unobstructed open water views from every room, this home boasts marble floors throughout and a spectacular ''floating'' staircase. Begin your day by stepping out of your master suite to your private and secluded bayfront terrace and into a second floor Infinity Edge pool. Just one step away from the main kitchen is an outdoor kitchen with adjacent bay view, al fresco dining. In the evening, slide open the numerous walls of glass to experience year-round, unobstructed open water views and the brilliance of Islamorada's sunsets from the privacy of your great room, bedrooms, gourmet kitchen or outdoor decks. For stargazing, venture up the spiral stairs to the rooftop deck for a breathtaking front row seat. Your boats will comfortably berth on the 100' dock with two boat lifts fitted with hurricane and storm surge protection. Other functional luxuries include an elevator, an enormous three-car, 2200 sf garage, complete with workshop and storage, professional camera/security system, central wet-dry vacuum system and mature landscaping with fruit trees. A fourth bedroom and bathroom can be easily added without modifying the structure or footprint at very reasonable expense. Built to withstand sustained 200 mph winds, this solid concrete constructed home also includes accordion shutters over impact glass for ultimate storm resiliency. Call today to view this private piece of paradise!

$5,299,000 - Upper Matecumbe Key Islamorada, FL

153 Stromboli Drive Upper Matecumbe Key Islamorada, FL - Exquisite Tri-Level Waterfront Estate in Islamorada!Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence boasts an open-concept floor plan with soaring ceilings, a fireplace and a grand living area.Enjoy seamless indoor-outdoor living with an expansive wraparound veranda, perfect for soaking in the breeze and relaxing water views. The beautifully landscaped 10,000sqft lot provides privacy and tranquility, while the swimming pool offers the ultimate relaxation.For boating enthusiasts, this property is a dream come true! Featuring 100' of deep-water concrete dockage equipped with a 20,000lb catamaran width elevator boat lift and a 5500lb set of davits you will enjoy immediate access to both the Atlantic Ocean and Florida Bay for excellent offshore and backcountry fishing. A two-car garage with a new A/C unit, plus additional covered carport parking, ensures ample space for vehicles and storage along with a beautifully paved driveway.Come experience the best of the Florida Keys lifestyle in this exceptional waterfront retreat!Updates....1. NEW 2-car Air Conditioning Split with 10-year warranty2. New Dock and Stair Brick Pavers3. New third-floor Impact Windows4. Two New third-floor Impact French Doors5. Two New third-floor electric Rolladen Hurricane Shutters6. Swimming poll resurfacing with new glass edge surround7. Dock has a 220-volt pedestal to service dock-side marine electric needs

$4,050,000 - Upper Matecumbe Key Islamorada, FL

150 List Street Upper Matecumbe Key Islamorada, FL - This remarkable 34,000 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 (65 ft), which has previously accommodated a 36-foot Bertram, making it perfect for boating enthusiasts. The property also offers ample space 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 aquatic species, like fish, birds, manatees, and a multitude of different birds. It's 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 property is one of the best on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation. May also purchase the vacant lot up front that has a Market Rate TDR on it. Combined you would have ability to build 2 large homes on a combined 49,000 of land. This would make an exceptional family compound in the heart of Islamorada. Possible owner financing. Owner / Agent

$3,495,000 - Upper Matecumbe Key Islamorada, FL

80639 Old Highway Upper Matecumbe Key Islamorada, FL - LAST New developer unit for sale in Maison Residences!Maison Residences #201, a 4 bedroom residence with 4.5 bathrooms features an open floor plan with a grand room and oversized covered terraces for oceanside living. So open and airy! The grand living room leads into casual dining, island seating and kitchen for gatherings during 'inside time'. This private enclave is nestled between the turquoise waters of the Atlantic Ocean and the Bay of Florida in the quaint seaside village of Islamorada. Maison is located on the Island of Upper Matecumbe Key- the most fun, artsy, beautiful island! It's situated within very private commons featuring more than 350 of natural sand beach, 155-foot day pier, with room for all water play activity. The most popular amenities are the lavish 86-foot lagoon-style pool, heated jacuzzi and the beach! After spending 'outdoor time' head to your private elevator which takes you to your private entryway. You'll walk into the grand living room leading to the terrace that overlooks the ocean, beach and pool. Gourmet kitchen provides storage a-plenty and counter space that includes the casual island separating the kitchen from the dining area. Upscale Sub-Zero and Wolf Gas appliances are featured. The grand room features 9-foot stacked sliders for entertainment flow out to the oversized terraces where entertaining is a must with multiple seating areas, large flatscreen TV, fireplace, and infrared/gas grill. The master suite features King-sized bedding, 9-foot sliders, luxurious tub bath and glass shower ensuite, with private terrace access. Three more Guest rooms feature King sized beds and bath en-suites, with two of the rooms featuring private balcony access. Detail: PRIVATE opening elevators into residence, 10-foot ceilings, Caesar-stone counters, porcelain tile, Sub-Zero and Wolf appliances, U-Line bev center, Lynx gas grill, Kohler plumbing fixtures, exceptionally furnished in luxurious comfort by design!

$2,950,000 - Upper Matecumbe Key Islamorada, FL

81250 Overseas Highway Upper Matecumbe Key Islamorada, FL - Only sophistication and class represented in Islamorada's most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off it's manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique charm blending Old Florida allure with the timeless essence of Nantucket. Covered parking and a versatile multi-purpose room on the ground floor with a foyer entry. On the second floor you will find an open living space with the kitchen & dining room overlooking the bay, 2 bedrooms/2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maid's quarters with more amazing views from the private balcony. If amenities are what you're after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare greenhouse to nurture your beloved plants, a waterfront pool & gazebo leading down to the beachfront, and plenty of dockage for your skiff. Come see the exclusivity of Tarpon Flats for yourself.

$2,850,000 - Upper Matecumbe Key Islamorada, FL

81250 Overseas Highway Upper Matecumbe Key Islamorada, FL - Experience refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket.This three-story home offers a thoughtful layout and spectacular bay views throughout. The ground floor features covered parking, a versatile multi-purpose room, and access through a gracious foyer entry. Upstairs, the main living level boasts an open-concept kitchen and dining area with panoramic bay vistas, two bedrooms, two bathrooms, and a tranquil porch ideal for enjoying sunset skies. The top floor is reserved for the expansive master suite, complete with a private balcony and sweeping waterfront views.Tarpon Flats offers an amenity-rich lifestyle tailored to the discerning buyer. Enjoy a waterfront pool and gazebo, private beachfront access, generous dockage for your skiff, a charming greenhouse, and a tennis court with shaded seating for guests. Adding to the ease of ownership, the community provides a full-time concierge service and an on-site handyman, ensuring both comfort and convenience year-round. Sophistication, privacy, and natural beauty converge in this exceptional Islamorada retreat--come discover what makes Tarpon Flats truly one of a kind.

$2,800,000 - Upper Matecumbe Key Islamorada, FL

33 Pen Key Drive Upper Matecumbe Key Islamorada, FL - 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 worlda'a 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; it's 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 you're 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.Don't just dream of the Keys, live it. Schedule your private tour today and experience firsthand what makes this home and private community so extraordinary.

Upper Matecumbe Key Islamorada, Florida listings for sale

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