Winter Park Mall, located in the heart of Winter Park, Florida, was hailed in the 1960s as a symbol of progress. The Mall was designed to compete directly for customers with nearby Park Avenue, the City’s traditional Main Street. During the 1980s and early 1990s, however, Winter Park Mall steadily declined in sales and lost tenants, while Park Avenue maintained its vitality and grew stronger. Park Avenue is now known as "the Main Street that killed the Mall."
In 1997, a consultant team from Dover, Kohl & Partners, Glatting Jackson, and Gibbs Planning Group devised a plan for the redevelopment of the Mall. Created on the City’s behalf, this plan was worked out in consultation with the prospective developer.
Winter Park Village was featured in the April 23, 2003 edition of USA Today, entitled "Makeovers Bring Life to New Malls." Winter Park Village was one of the earliest mall redevelopments in the country.