5. Port Charlotte, Florida
About halfway between Sarasota and Fort Myers and northeast of historic Punta Gorda, Port Charlotte in Charlotte County boasts the best of both worlds, the old and the new. Quaint, yet modern, it has gained a well-deserved reputation for its unhurried and laid-back lifestyle. The area itself was long underdeveloped until the post-war boom in the 1950s.
Based out of Miami, Elliot, Robert, and Frank Mackle Jr. and their land development company the General Development Corporation would transform the whole area turning it into one of the most desirable places to retire in the US. Its retiree-friendly tax code, quality health care, and desirable amenities only add to that.
Total population: 59,654
Median list price: $220,000
Percentage of population 65 and older: 30%