DiMatteo Insurance’s Story

Our Story and Why It Matters

Our story begins at our core, we believe in giving back, contributing, educating and service.  Each and every day we strive to add value to the lives we touch – be it our customers, our employees or our friends and family.

Our successes since 1960 are directly related to this philosophy of giving instilled in us by our Founder, Tony DiMatteo – it’s what allows our story to continue on year after year.   He reminded us to always put the interests of others first, and the abundance will in turn follow.  We’re pretty sure he was on the right track, because those lessons continue to live with us today.

Our Story Picture of Founders DiMatteo Insurance
DiMatteo Insurance -Picture of partners on stairs in office

At DiMatteo Insurance you’ll always see a smiling face, hear a helpful and calming voice and know that we will be here to advocate for you.   We are continually expanding our knowledge to better serve you and to be the best we can be. This includes our recent partnership with Cross Insurance. You can learn more about Cross Insurance by visiting their website: crossagency.com.

Lastly, our doors are always open.  If there is a problem or a concern we want to know, don’t ever hesitate to connect with us and ask for help.

The DiMatteo Family Charitable Foundation

Created to honor our Founder, the late Anthony “Tony” DiMatteo during his battle with cancer, the DiMatteo Family Charitable Foundation has raised over $300,000 dollars for various well-known local and national charities.

DiMatteo Family Charitable Foundation logo

1960: A.A. DiMatteo Insurance Services Center was Born

The late Anthony “Tony” DiMatteo and Adeline DiMatteo started A.A. DiMatteo Insurance Service Center in Bridgeport, CT doing auto, home, and life insurance.

1986: The Family Business Grows

Loretta DiMatteo Lesko was the first child of Tony & Adeline’s to join the business.

1988: And Grows…

Tony and Adeline’s son and Loretta’s brother, John DiMatteo joined the business.

1990: And Grows…

John’s wife, Kim DiMatteo, joined the firm and soon after the business focus shifted towards Commercial Insurance with greatly accelerated growth and expansion.

1993: The Big Move

With both the firm and team growing, the business relocated from their 1000 sq. ft Bridgeport office to an 1800 sq. ft office on Main St. in Trumbull.

1995: The Family Expansion Continues

Additional children and family members joined the business: Rosemarie DiMatteo Esposito, Victoria DiMatteo, and Rob Lesko.

2003: The Move to Shelton

After continual growth over the past decade,  the firm relocated again and now resides at their current location in a 5,000 sq. foot building on Bridgeport Ave. in Shelton.

2005: The Birth of the DiMatteo Charitable Family Foundation

Created to honor our Founder, the late Anthony “Tony” DiMatteo during his battle with cancer, the DiMatteo Family Charitable Foundation was born. The annual golf event held by the Foundation raises funds to support various local charities.  It is completely run by DiMatteo Insurance staff and volunteers to maximize the proceeds to our community.

2010: The Legacy Lives On

The late Tony DiMatteo passed away however his legacy lives on with this foundation, the business and family members.

2019: Family Leadership Continues

Loretta Lesko and Kim DiMatteo lead the insurance department with over 20 employees with Rob Lesko as a senior producer of commercial lines.

2019: Joining Forces with Cross Insurance

Dimatteo Insurance joins forces with Cross Insurance – a family owned insurance agency made up of a network of wholly-owned subsidiary insurance agencies throughout Maine, New Hampshire, Massachusetts, Connecticut, New York, and Rhode Island. Getting its humble beginnings in the home of Woodrow Cross in 1954, the company has since grown to become one of New England’s largest independent insurance intermediaries and the nation’s 33rd largest broker of U.S. Business, with over 40 branches and more than 800 employees.