In the latter part of the 19th century, doctors prescribed warm climes and a peaceful environment as a remedy for a variety of ailments and, to Chicago businessman Loring Chase, Winter Park, Fla., seemed the perfect spot for recovering from his chronic bronchitis. Once there, the area's lush, fertile land and string of crystal-clear lakes appealed to the entrepreneurial spirit of the former real estate broker, so Chase and an old friend, Oliver Chapman, plunked down $13,000 for 600 acres in order to build a town. Together they plotted out what would become the first planned community in Florida, with neat grids for houses and space set aside for schools, parks, shops, and municipal buildings. Over the years, Winter Park attracted many residents and visitors interested in the arts, and the city became well known for its art and music festivals and events. Another attraction, less highbrow but popular nonetheless, was the famed Winter Park sinkhole, a ground collapse that, over the course of one day in 1981, grew to more than 300 feet in diameter, swallowing a grove of trees, homes, and a car dealership. Today, it is just one more of the area's lovely lakes.

Learn more about markets featured in this article: Chicago, IL, Orlando, FL.