Islamorada Real Estate Search

Newest Islamorada Homes and Condos for Sale

$6,999,000
5 Beds 6 Baths 611760 MLS
Welcome to Southwinds, your exclusive oceanfront oasis in the heart of Lower Matecumbe, Islamorada. This stunning 5-bedroom, 6.5-bath CBS home embodies luxury and tropical living. Spanning nearly 4,000 sq. ft., Southwinds offers breathtaking ocean views, with floor-to-ceiling impact windows that flood the interior with natural light, seamlessly connecting you to the stunning beauty of the Atlantic. One of the standout features of Southwinds is its 100' natural sandy beach, a rare find in Keys oceanfront homes. Stroll the 150' foot pier which features water, electric and a fish cleaning station. Read a book or enjoy your favorite beverage under the tiki. The pool features a spillover edge, bubbler, sun shelf and hot tub. The grand outdoor Mahogany bar is ideal for entertaining against the backdrop for the ocean breezes. A private pickleball court offers hours of fun and fitness for you and your guests, right in your own backyard. Paired with a putting green, this home provides a truly unique lifestyle experience that caters to the active, outdoor enthusiast.The home features a large kitchen with a pass-thru, an induction range, wine and beverage coolers, and two sets of washers and dryers for ultimate convenience. The third-floor wet bar and expansive open balconies offer additional space to enjoy the spectacular views. The gated property also features landscape lighting, an irrigation system, a spacious garage, and storage room.Southwinds is a sanctuary for those seeking a private retreat or a valuable investment. Whether you're in search of a second home or a high-performing rental property, this residence offers everything you could desire. Zoning allows for weekly vacation rentals, Southwinds presents an ideal opportunity for generating rental income.

75851 Overseas Highway, Islamorada

$13,995,000
7 Beds 9 Baths 611489 MLS
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.

83283 Old Highway, Islamorada

$545,000
2 Beds 2 Baths 611462 MLS
Least expensive oceanfront lot with immediate building capability!! Owner wants offer! RARE FIND.....BUILDABLE OCEANFRONT LOT WITH RV. Oceanfront Slice of Paradise in the Florida Keys! INCREDIBLE OCEAN VIEWS. Owner has quote $250k from start to finish to put in a Jacobsen Top of the line Modular Home, ask for details. BUILD with a Development Right Letter from the Village of Islamorada in hand, no wait to build your dream home! Located in fabulous Islamorada with Multi-Million Dollar Views! Currently livable 1 bedroom and 1 bath RV on lot. RV cannot be replaced with another RV-if removed must build. Lot is on solid coral rock-not fill. Future potential is to build a modular or concrete home on stilts for one or two levels of living area. Owner also has engineered plans for a 2/2 concrete home that can be provided to buyer at no charge (6,000.00). Very easy to build either CBS or modular on this lot with no hassles from Village of Islamorada Letter In Documents. Perfect for primary home or vacation spot to enjoy magnificent Florida Keys sunrises and sunsets. Complex amenities includes dock privileges, boat storage, fish cleaning station, common oceanfront jetty and boat ramp-ask for more details. You own the land in a neighborhood comprised of 48 units with low monthly fees at 139 a month. Two domestic pets allowed any size. Only a couple miles away from Heart of Islamorada offering the Art District, Restaurants, grocery store, gym and more. Fantastic bike path for the bikers, runners and walker enthusiasts. Hurry this will not last!!! Owner Finance may be possible, please inquire.

84961 Old Highway Unit #19, Islamorada

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Islamorada Homes for Sale

Stretching across just over seven square miles halfway between Key West and South Miami, the waterfront community of Islamorada is a great place to buy a home in Monroe County, Florida. Encompassing Tea Table Key, Upper and Lower Matecumbe Key, Windley Key, and Plantation Key, the community is also called Village of Islands. The community was just a part of Upper Matecumbe Key until it was incorporated in 1977. It is located in the center of the one-hundred-mile-long Florida Keys, between Mile Markers 72 and 90. Altogether its four islands span eighteen linear miles with a thin land area of just under four thousand acres.

This naturally beautiful community has strict land development regulations as do most of the islands in the Florida Keys. It is an incredibly popular destination for anglers, particularly in the backcountry that abuts the Gulf of Mexico. In fact, it is known as the Sport Fishing Capital of the World. It also has fabulous fishing opportunities on the opposite shore, conveniently out of reach from the Gulf Stream. Home to just over six thousand, six hundred people, Islamorada sees a lot of second-home owners and vacationers and offers a wide variety of services and amenities. For example, there are some fabulous micro-beer breweries, art galleries, shops, and restaurants here, including must-try places like Whale Harbor Restaurant, Pierre’s, Kaiyo Grill & Sushi Bar, Ziggie & Mad Dogs, and Chef Michaels, to name a few.

Islamorada is also home to beautiful sandbars and parks, including Founders Park which encompasses a sandy beach, aquatic center, and Plantation Yacht Harbor Marina and its eighty-three wet slips. All of these advantages contribute to the irresistibility of Islamorada real estate. Real estate in Islamorada include stunning oceanfront estates, two- and three-story stilt homes, and a variety of oceanfront condos. There are roughly five thousand seven hundred homes in this Village of Islands, and they include Islamorada oceanfront homes and inland properties. These also include Islamorada vacation homes. Whatever it is you seek, we would love to share details about specific properties available in Islamorada, Florida, so please contact us today so we can help you with your Islamorada home search.

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