A 12-mile barrier island between the sun-drenched waters of Sarasota Bay and the Gulf of Mexico, Longboat Key has long been a favored destination of globe-trotters and U.S. residents alike. Located half in Sarasota County and half in Manatee County, this island paradise is home to nearly 8,000 permanent residents. The island is especially popular with retirees and second-home owners, who boost the population to as high as 20,000 in peak season.

The south end of the Key is one bridge away from St. Armands Circle, a renowned shopping and dining destination, as well as Lido Beach.

The main thoroughfare is the beautifully landscaped Gulf of Mexico Drive, which runs the full length of the island with only two stoplights, past magnificent homes and condominiums, verdant greenways and parks, yacht basins and discreet plazas for upscale shopping and fine dining, as well as the two championship golf courses of the Longboat Key Club.

On the Gulf of Mexico side, condominium communities occupy the south end, with prices ranging from $400,000 to $5 million. The north end has fewer condos and more private single-family homes. A beachfront cottage here may go for $1 million, with larger homes ranging from $2 million to $6 million. On the Sarasota Bay side, offering spectacular views of the Sarasota city skyline, canal and bayfront homes can be found from $500,000 to $6 million, while condos range from $250,000 to $3 million.