What It’s Like to Live in the Upper Keys

Upper Florida Keys
Upper Florida Keys FTL file photo

Once you reach the end of the 18-mile stretch of asphalt tethering the Florida Keys to the rest of the world, you’ll find that life moves to the tempo of a reggae song. The archipelago is perched on an ancient coral reef, nestled between the aquamarine waters of the Atlantic Ocean and the Florida Bay. Small-town island living is both what initially draws people here and, later, what anchors them. Most residents, after they tell you how they came and fell in love with the Keys, will conclude: “I just never left.”

The enchantment starts in Key Largo and Islamorada. Known as the Upper Keys, these islands sit at the top of the chain, which is connected by a series of 42 bridges. Needless to say, water is the attraction. “The cusp of our community either boats, fishes or dives, so water amenities and access are important,” says Joy Martin, broker and owner of Marr Properties and American Caribbean Real Estate. The 33-mile-long island of Key Largo is bordered by John Pennekamp Coral Reef State Park to the east, which is home to North America’s only living barrier reef and is a big draw for divers. To the west is Everglades National Park, easily accessible to boaters. A look in the canals that weave around the islands reveals manatees, spiny lobsters and mangrove snappers.

Bill and Kim Cook, dive enthusiasts from California, came looking for a second home. Key Largo’s status as the diving capital of the world drew the couple in — it was perfect for pursuing their underwater-photography hobby. “We dive here regularly and looked at homes several years ago,” Bill says. “Last year, the prices dropped dramatically, so we thought it would be a good long-term investment, as well as a fun place to live.”


An airy four-bedroom home, with 20-foot-high pine ceilings and a mosaic outdoor bar, proved too much for the Cooks to resist. One of the selling points that sealed the deal was the home’s location on Adams Waterway, a man-made shortcut from ocean to bay called “the cut.” “We enjoy watching the boat traffic going by,” Bill says. “We’ll go out for a sunset cruise and catch some fish for dinner.”

Located an hour south of Miami, Key Largo is the epicenter of the Upper Keys. Chain supermarkets, discount stores, pharmacies and professional offices are all centrally located. “We have everything we need, but if you’re expecting Neiman Marcus, you’re not going to find it here,” Bill says. “It’s a very casual lifestyle.”

Most of the restaurants are still funky independents. The Fish House is a mainstay for the daily catch. At lunchtime, Mrs. Mac’s Kitchen causes mini traffic jams with its down-home cooking that’s easy on the wallet, and Snapper’s oceanfront tiki bar is a favorite local gathering spot every Thursday.


With the Florida Keys’ tourism-driven economy and temperate climate — the Upper Keys have never hit 32 or 100 degrees — most buyers are shopping for second homes. Northerners want winter residences, and Floridians seek summer getaways.

However, Key Largo is also part bedroom community for Miamians who work in the city; it has more full-time residents than neighboring Islamorada. A single-family home on a dry lot — not on the ocean, bay or canal — in the Key Largo Beach neighborhood (a mix of old and new homes) starts at

Neighboring Islamorada is a village with four narrow keys: Plantation, Windley, Upper Matecumbe and Lower Matecumbe. Known as the sport-fishing capital of the world, the area is extremely popular with anglers, who find ocean and bay access via a series of eight bridges. “Islamorada is a bit more upscale with more valuable properties,” Martin says. “You have the area called Millionaires Row on Plantation Key, where award-winning Hollywood producer Jon Landau [of Avatar fame] purchased the four-acre oceanfront estate Bali Hai for $5.8 million.”


Two years ago, Rick and Cindy Freeburg relocated from Miami to Plantation Lake Estates when Rick became CEO of Mariners Hospital. They bought a three-bedroom home on a lagoon for just under $1 million. “We used to visit the Keys regularly, so when the job opportunity came, I felt like we hit the lotto,” Rick says. “We love being in a small-town atmosphere. The servers know our names at the Islamorada Fishing Club, and it’s been the source of many of our closest friends.” He insists that being on the water is what made the deal so sweet, adding, “We’ll boat to restaurants, especially Island Grill. We snorkel and fish, or we’ll just go out for a picnic, anchoring at Alligator Lighthouse.”

Laurie Wickham, owner of Gallery Morada, and her husband, Dick Hagood, a backcountry fisherman, are 29-year residents living on Upper Matecumbe — Islamorada’s downtown.

The village’s former ban on chain stores resulted in one-of-a-kind boutiques, art galleries and upscale restaurants. Although the law was recently overturned, square-footage allotments for new developments remain scarce. “It’s not as commercial as Key Largo. I drive 20 miles every week to Publix, but I’d rather live here,” Wickham says.


She is often spotted bicycling or walking along the pedestrian-friendly Old Highway, which runs parallel to U.S. Highway 1. The shade of old-growth poinciana and buttonwood trees creates a quiet refuge, interrupted by the occasional wild peacock call. “Islamorada feels more like island living to me.”

This laid-back Upper Keys lifestyle has tempted homeowners for years, yet few get to indulge. Since the area is environmentally sensitive, building during the housing boom that peaked in 2006 was mostly limited to redevelopment of existing properties. For anyone shopping the real-estate market now, Martin says, “There’s confidence buying where there’s not a glut of inventory.” However, “As the inventory is absorbed, there will be fewer deals.”


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