In 1960, the late Anthony “Tony” DiMatteo and Adeline DiMatteo started A.A. DiMatteo Insurance Service Center, located on the lower east side of Bridgeport.  They primarily provided auto, home, and life insurance but added tax preparation services soon after.  The office moved to Huntington Tpke Bridgeport around 1970.  Loretta “DiMatteo” Lesko was the first child to join the business in 1986 and then John DiMatteo joined in 1988.  The firm focused at that point in offering business insurance which grew very rapidly once John’s soon to be wife Kim DiMatteo joined the firm in 1990.  The financial services department was also added in the early 1990’s spearheaded by John DiMatteo as a certified financial planner offering Retirement Planning and college funding.

The firm outgrew the small Bridgeport location (under 1000 sq ft.) and moved to Main St. Trumbull in 1993 (1800 sq ft).  Rosemarie DiMatteo Esposito, Victoria DiMatteo, and Rob Lesko joined the firm in the mid 1990’s.  The next stop in  2003,  was Bridgeport Ave. in Shelton with over 5,000 square feet and over 20 employees. 

Today,  Loretta Lesko and Kim DiMatteo lead the insurance department with over 20 employees while John DiMatteo leads the financial services department and Rose Esposito leads the tax and accounting department.  Rob Lesko is a senior producer of commercial lines and also plays a key role in the tax and accounting department.

The third generation joined the firm when John Esposito came on board in 2016, and we are all hopeful to see others from the third generation join the firm.

The DiMatteo Family Charitable foundation was created in 2003 and uses an annual golf event’s proceeds to support various local charities.  This was done when Tony DiMatteo was battling colon cancer.  Tony passed in 2010 and to date the foundation has raised approximately $400,000 and is completely run by DiMatteo Group staff and volunteers to maximize the proceeds to our community.