Escape to the Conch Republic: Islands of the Florida Keys

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Proving that you don’t need to travel far to find a perfect sun-swept tropical isle, the Florida Keys offer Americans an exotic getaway right in their own backyard.


Ragged Key – 8 Acres – US$ 5 Million

Beautiful Private Island located in Biscayne Bay just 18 miles from Miami. Property features two guest houses, above ground pool and dockage.

A secluded chain of 1700 islands stretching from cosmopolitan Miami down to colourful Key West, the Florida Keys are the notable exception to America’s image as a place for rustic cottage islands. With a laid-back culture and a feeling of pleasant isolation from the mainland, the Keys have long exerted a gravitational pull on artists, writers and other eccentrics seeking to escape from the urban world… and more than a few unsavoury types on the run. Cemented in the public imagination as an underworld haven by Noir films like John Huston’s 1949 “Key Largo”, and a storied history as a hideout for pirates and smugglers, this slightly shady reputation seems to have only added to the islands’ romantic allure. And while the Keys may have undergone some gentrification over the past decades, the 1980’s move by the mayor of Key West to secede as the “Conch Republic” speaks volumes about the sleepy chain’s still-independent character.


Ballast Key – 23 Acres – US$ 13.8 Million

The celebrity owner of this island in the heart of the Keys has entertained the likes of Tennessee Williams, Truman Capote and Dick Cavett.

Our tour of the Keys starts just south of Miami in Biscayne Bay, with one of the swankiest private islands to hit the American market. This long lagoon is home to several highly exclusive communities where you’ll find the homes of celebrities and some of Miami’s top executives, and manages to retain a natural feel even with the metropolitan skyline in the distance. Our first island’s name of Ragged Key may sound a little rustic, but the ultra-modern residence is surrounded by manicured grounds and comes with guesthouses, a pool, and just enough untouched land to add a little sense of wilderness. This 8-acre property is offered at US $5M, and for those who crave even more opulence or want to make a permanent move to the Miami area, an option to purchase the island together with a luxurious nearby mainland estate is available.


Fanny Key – 1.7 Acres – US$ 8 Million

The ultimate in luxury awaits you on this beautiful Florida Key, complete with a perfectly appointed home, freshwater pool, and unique lagoon.

The town of Duck Key is the next stop down the archipelago, with a rare opportunity to purchase two twin islands near this upscale community. Surrounded by excellent diving and close to all amenities, Tom’s Harbor Keys are prime for development into a resort or residential complex. Located right by multi-million dollar mainland homes, they total 46 acres and are offered at a very reasonable US $2.9M. Heading south towards the tip of the chain is the sleepy town of Summerland Key, an area that sees a fair amount of private island activity. Listed at US $4.5M, the 9-acre Howell Key is a rare larger property that currently offers adventure camping to guests, and could be further commercially developed or kept for personal use. Also close to Summerland is the celebrity-owned Melody Key, a relaxed and modern island retreat with a price that’s just been reduced to a highly attractive US $4.9M.


Howell Key – 9.5 Acres – US$ 4.5 Million

This jewel in the Florida Keys is an excellent prospect for tourist development, featuring extensive building permits and quintessential Keys charm.

One of the biggest towns in the Keys, the city of Marathon is spread over a number of individual islands, and prides itself on having a perfect combination of history, nature and sophistication. Here you’ll long sandy beaches, incredible fishing and the famous Seven Mile Bridge, which stretches across the ocean and is considered by many to be one of the most picturesque drives in the world. The little 1.7 acre Fanny Key is only private island found for sale in the Marathon area, and you can enjoy its beautifully designed home and sunset views for $8M. Concluding our tour, at the tail end of the Keys is an incomparable estate and one of the few private islands found in the pristine Key West Wildlife Refuge. With 26 acres of white sand beaches and tropical forests, the $13.8M Ballast Key has provided a relaxing retreat for cultural luminaries like Tennessee Williams and Truman Capote. A short distance from the city of Key West, the island is also the southernmost inhabited point of the continental USA. Continue any further and you’ll only find little barren islets, and after a few hundred empty miles, eventually reach Cuba.


Melody Key – 5.5 Acres – US$ 4.9 Million

Everything you need is included in the sale of Melody Key: a fully furnished house, pool, two boats, and a canal lot on the mainland.

From Miami’s Biscayne Bay to the most remote reaches of the American continent, each of these islands offers a special kind of luxury, and an opportunity to create a new lifestyle within the vivid culture and natural beauty of the Keys. While their price point may be slightly higher than that of properties found in the lakes and rugged coasts of the northern states, Florida’s private islands are exceptionally well-priced when compared to the tropical isles for sale in the Caribbean, and have the added advantage of American property laws and ease of development. And unlike more exotic areas of the world, a majority of the islands on the market in the Keys are close to abundant shopping and fine dining, come in a finished state with a modern home ready to be enjoyed, and are easily accessed through numerous regional airports. Perfect for those who crave independence without the challenges of being truly remote, your piece of the Keys may not be your own Conch Republic, but will feel just close enough.


Tom’s Harbor Keys – 46 Acres – US$ 2.9 Million

The Tom’s Harbor Keys constitute two separate islands in the Atlantic, just south of Hawk’s Cay Resort. A perfect development prospect, the islands total 46 acres.

For more information on private islands for sale in Florida, please see: