Upper Matecumbe Key Islamorada Homes on the Bay / Gulf Side For Sale

This lovely home is classic Keys on the outside, with modern elegance on the inside. Secluded on high ground in the heart of downtown Islamorada, this accommodating three-bedroom, two-bath residence offers abundant space for relaxation and entertainment, including an inviting back porch, surrounded by lush landscaping that enhances the serene atmosphere. The expansive front and back yards provide ample room for outdoor activities and gatherings. Ideally situated, you are within easy walking distance to the beaches, great restaurants, and grocery shopping. Experience the perfect blend of comfort and convenience in this idyllic retreat.

This beautiful 4-year-old ground-level home features 3 bedrooms and 2 bathrooms. The kitchen boasts stunning all-wood cabinets, granite countertops, and stainless steel appliances. Marble tile floors extend throughout the house, creating a luxurious and cohesive feel.The home includes a large screened porch off the back two bedrooms, perfect for enjoying the surrounding tropical tree canopy. The house is well-lit with all LED lights and features ceiling fans inside and on the porches, providing comfort and energy efficiency.The bathrooms have been thoughtfully designed with backing that will allow for the installation of handicap bars, ensuring accessibility for all. The two-car garage with doors at the front and back provides easy access to the backyard. The low-maintenance landscaping is complemented by a sprinkler system, making upkeep a breeze.For those with a penchant for boating, the home is conveniently close to marinas. Additionally, it is near shopping facilities and some of the best restaurants in the Florida Keys, offering a blend of convenience and leisure.

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.

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!

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

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 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.