"Coverage with Confidence"

Serving Central Florida Since 1919

It all began in 1919 when W.J. Lawton had a desk in the back of his grocery store.  He 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 Bill Winchester and Vice President Lori Forrest of Oviedo.  The staff consists of :

  • Diane Spencer, Agent
  • De Allen, Agent
  • Lou Traeger, Agent
  • Carol bergman, Agent
  • Jeff Woodward, ChFC, CLU
  • Rachelle Rich, CSR
  • Sue Wentworth, CSR
  • Peggy Peterson, Administrative
  • Lori Contreras, Administrative
  • Becky Carroll, Administrative

Winchester Insurance strives to provide our clients with personalized service and insurance products tailored to their individual needs.  Today we represent over 15 national insurance carriers handling over 3,000 clients.

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1425 W. Broadway Street
Oviedo, Florida 32765

(407) 365-5656
Fax: (407) 366-0031

Our Mission:
Winchester Insurance, Inc. regards the insurance business as an opportunity to serve society. Our agents strive to render the full measure of service that would be expected from an Independent Agency. We analyze the insurance needs of all our clients, and to the best of our ability, recommend the coverage to suit those needs. Our goal is to provide the public with a better understanding of insurance.