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The funky beach town of Key West, Florida is the southernmost point of the continental United States, a true Land’s End with a laissez-faire attitude that pairs perfectly with sherbet-coloured houses, spectacular sunsets and semi-tropical breezes. Going your own way is not merely tolerated – it is actively encouraged.

What is it known for?
Geographically closer to Havana than Miami, the coral reef-filled waters off Key West often  resemble those found in the Caribbean. But the Conch Republic, as it is known, has a character all its own. This is the town that inspired Jimmy Buffett’s song Margaritaville, after all. Free spirits, soul searchers, artists and anyone who wants to be a part of such a community have all drifted down to be part of One Human Family, Key West’s official philosophy of inclusion.

“Key West attracts everyone – rich or poor, old or young, famous or infamous —interesting people find their way to Key West,” said Perry Collier, who, with his wife Sue, spends winters in their 100-year-old house in Old Town. “When you’re out on the town, listening to great live music, you never know who you will meet.”

The town attracted writers like Ernest Hemingway, who lived here in the 1930s, and during his term in the 1940s and ‘50s, former US President Harry Truman spent a lot of time at the gracious Little White House, not far from Duval Street, Key West’s main strip. Lined with small boutiques, open-air bars and music clubs like Sloppy Joe’s (where Hemingway drank and where bands play every night of the week), Duval Street attracts tourists, cruise ship day-trippers and packs of Harley-riding visitors who mingle with the locals. The harbourfront watering holes, such as the bar on Sunset Pier are also packed, especially at day’s end, when, sundowner in hand, everyone watches the daily crepuscular show. “When the geese head south and the skies turn grey [in New Jersey]. I know I need to be [in Key West], where every morning it’s going to be another sunny day,” Collier said.

The streets surrounding Duval are part of the Key West Historic District, including Old Town, which is filled with 19th-century one- or two-storey wooden Conch-style houses (brought by Bahamian immigrants), with wide-planked porches, intricate pastel-coloured trim and lush gardens filled with jasmine and bougainvillea. Sitting on the porch is a sure way to make friends and chat with neighbours, and it is a perfect place to watch events like the annual Fantasy Fest parade during Key West’s answer to Mardi Gras, held at the end of October. The slower pace of life and Key West’s compact size mean the best way to get around is on two wheels or on foot.

Where do you want to live?
Key West is linked to the mainland and the rest of the Florida Keys by a single highway, US Route 1, and it runs through New Town, which looks very different from Old Town, with fast food restaurants and waterfront condo buildings.

The most popular places to live are in the historic district of Key West, in the charming neighbourhoods clustered at the water’s edge. “The historic district is the most popular with out-of-town buyers,” said Rudy Molinet, principal broker and co-owner of Marquis Properties Realty. “These include Old Town, Casa Marina, Truman Annex and the Meadows, all within walking district to restaurants, bars, water sports and cultural activities.” Property-seekers come from all over the US and Canada, as well as the UK, France and Italy, and the most sought-after properties are single-family homes in the Old Town area. “Key West is a city built on diversity, so our buyers come from everywhere and all walks of life,” said Molinet.

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