Our Story and Why it Matters

At our core, we believe in giving back, contributing, educating, and serving. 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. 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.

At the DiMatteo Group, 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.

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.



Dim partners



Our History: It all started in the '60s

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, Connecticut, offering auto, home, and life insurance, and then added tax preparation services soon after.


1986 – The Family Business Grows

Loretta DiMatteo Lesko was the first child of Tony and Adeline 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 toward commercial insurance, with greatly accelerated growth and expansion.


1991 – Financial Services Added to the Roster

The financial services department was added and spearheaded by John DiMatteo as a CERTIFIED FINANCIAL PLANNERTM professional, offering retirement planning and college funding.


1993 – The Big Move

With both the firm and team growing, the business relocated from a 1,000-square-foot Bridgeport office to a 1,800-square-foot office on Main Street in Trumbull.


1995 – Family Expansion Continues

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

2003 – Move to Shelton

After continual growth during the past decade,  the firm relocated again and now resides at its current location in a 5,000-square-foot building on Bridgeport Avenue in Shelton.


2005 – Birth of 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 was born. The annual golf event held by the foundation raises funds to support various local charities. It is completely run by DiMatteo Group staff and volunteers to maximize the proceeds to our community.


2010 – The Legacy Lives On

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


2016 – Third Generation

John Esposito, the first of the third generation DiMatteos, came on board as a paraplanner on the financial team.


2018 – Family Leadership Continues

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


2020 – A New Chapter

Effective 2021, DiMatteo Insurance will have completely merged with ACBI, another local agency in Shelton, Connecticut. The status quo will remain with both the financial and tax departments. John DiMatteo will still be leading the financial services business with the help of his nephew, John Esposito. Rosemarie Esposito will continue to head the tax and accounting department, with Loretta and Rob Lesko playing key management and servicing roles.


2021 – Third Generation, Round 2

Jessica DiMatteo, the second of the third-generation DiMatteos, came on board as an assitant on the financial team.