Our Story

Our Story and Why it Matters

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.   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.

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.

Our History

It All Started in the 60’s


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 but added tax preparation services soon after.


The Family Business Grows

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


And Grows....

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


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.


Financial Services Added to the Roster

The financial services department was added spearheaded by John DiMatteo as a Certified Financial Planner offering retirement planning and college funding.


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.


Family Expansion Continues

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


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.


The 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.


The Legacy Lives On

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


Third Generation

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


Family Leadership Continues

Today – Loretta Lesko and Kim DiMatteo lead the insurance department with over 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.

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