It all began in 1919 when W.J. Lawton had a desk in the back of his grocery store and dealt only with Hartford Insurance. Then, in 1965 Ben F. Ward bought and expanded the business and after several years of operating a building, real estate, and insurance business. Ward sold the Ben Ward Insurance Agency to Harvey Winchester from Massachusetts. Winchester formed Gale, Ward & Winchester along with Jack L. Gale, a prominent Central Florida real estate agent. The firm grew with the town of Oviedo in the 70's and 80's. In 1984, the brick colonial building which now houses the agency was built.
In 1991 Bill Winchester and Lori Forrest bought the agency. Currently, the office is managed by President, Lori Forrest.