Islamorada, FL

The Most Expensive Homes in the Florida Keys

Toni Koraza
Photo by Jensen R.

The Florida Keys are a string of stunning tropical islands located about 120 miles from the southern tip of Florida.

Available home rentals boast a variety of vacation condos, beach houses, and homes in Islamorada, Key Largo, Key West, and other popular Keys. To give you an idea of their grandeur, we’ve gathered a list of the top three most expensive houses in the Florida Keys.

Palm Harbor at 80999 Old Hwy, Islamorada, FL 33036

Zillow lists Palm Harbor as one of the most stunning and exquisite estates in the Florida Keys, coming in at $23,000,000. This spectacular tropical destination is on the Atlantic Ocean, nestled on a beachfront, and it has a private harbor and peninsula. Furthermore, the location is on the highly-esteemed Green Turtle Beach in Islamorada, Florida Keys.

Inside of the main house is over 7,500 square feet, with four baths, four bedrooms, two half baths, a crow's nest, outdoor showers, lofted card/game room, lofted card/game with parking to boot. The guest house features two baths, two bedrooms, a caretaker's office, storage, and two garage bays.

Ocean Tranquility at 88011 Old Hwy, Islamorada, FL 33036

Oceanside Tranquility is a gorgeous home located near the Old Highway. The views are spectacular, and it sits on more than seven acres of land. The entrance is private and begins with a long and winding road that leads you to the main home. You'll find five bedrooms and 5.5 bathrooms, totaling 6,652 square feet.

Also, two exquisite staircases separate the two sections of this extensive property. The main house has floor-to-ceiling windows, 450 feet of sandy shores out front, and a home library.

The guest house on this property is 1,161 square feet, with two large bedrooms with a private bathroom. A hot tub and private, heated pool separate the main and guest houses. At $10,900,000, this is one of the most luxurious homes in the Keys.

Lush Landscape at 20 Avacado St, Islamorada, FL 33036

This location brings you endless sunset views and 1.5 acres of lush landscape. In downtown Islamorada, the estate overlooks the Florida bay. The main house has four massive bedrooms, six bathrooms, a home gym, a media room, ample closet space, an office, multiple elevators to access any area in the home, and more.

The guest house has two bedrooms, two bathrooms, a separate laundry facility, and a 1300-square foot boat basin, which offers plenty of space for docking boats, jet skis, and other water sports equipment. Overall, it will cost $10,750,000 to move into this beauty with cathedral ceilings and nearly 7,000 sq feet.

What's your favorite Florida Keys house?

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