About Us
Core Values
Learning and Evolving
We employ a dedicated work ethic to continuously learn and develop.
Put The Client First
As a values-based organization, we put our client needs before our own.
Be A Go Giver
We give more in value to those around us than we take in payment. We give back to the community that we serve in a meaningful way.
Do What You Say
We do what it takes to execute and keep clients informed along the way. We strive to provide accessible, responsive service and consistent follow through.
Celebrate
We recognize individual and shared accomplishments and celebrate these experiences by telling stories, sharing laughter, and having fun.
Our Passion
Serving as our client's first call for guidance.
Our Niche
Help people prepare for and enjoy a confident retirement.
We Are A Valuable Resource
Our team provides meaningful guidance and an elevated standard of care to support your needs.
We Look At Your Whole Picture
We understand not only financial planning, but also risk management & insurance planning, investment planning, tax planning, retirement savings & income planning, and estate planning. Our goal is to have each piece work together to better position & preserve your assets in a dynamic manner.
We Are A Multigenerational Owned & Operated Firm
We strive for an impeccable reputation in the community we serve, and we intend to uphold it.
I’ve been doing business with the DiMatteo family for over 25 years and working with the third generation of family members. They’re more than a business acquaintance, they’re like a family. Thank you for all your support throughout the years.
- Jose Costa
The statement was provided 05/19/2023 by Jose Costa who is a client. This statement may not be representative of the experience of others and is not a guarantee of future performance or success. For additional reviews, search us wherever local businesses are reviewed.
DiMatteo Group Financial Services breaks complex financial matters down into understandable terms and they are always available for me when I have questions or concerns. I feel very comfortable because of the family atmosphere DiMatteo Group provides, and I trust that they are proactively looking out for my interests at all times. I especially like the timely and reassuring market updates during volatile times.
- Joseph Gessaroli
The statement was provided 05/17/2023 by Joseph Gessaroli who is a client. This statement may not be representative of the experience of others and is not a guarantee of future performance or success. For additional reviews, search us wherever local businesses are reviewed.
My wife and I have been very happy with the financial advice from the DiMatteo Group for a long time. We strongly recommend John and his staff to potential future clients. We are also happy with the coordination that exists with the DiMatteo tax services especially his sister Rose who has been doing our taxes for many years. This is a wonderful family run business.
- John DaPonte
The statement was provided 6/30/2024 by John DaPonte who is a client. This statement may not be representative of the experience of others and is not a guarantee of future performance or success. For additional reviews, search us wherever local businesses are reviewed.
I have been working with the DiMatteo Group for over a decade, and I couldn't be happier with the level of service and expertise I've received. John and his team have been instrumental in helping my family navigate through various financial decisions, from investments to retirement planning.
What stands out the most is the DiMatteo Group's deep knowledge of the market and their ability to explain complex financial concepts in a clear and understandable manner. They took the time to understand my financial goals and tailored a plan that aligns perfectly with my objectives.
Their professionalism and responsiveness are top-notch. Whenever I have questions or need clarification, John and his team are always there to provide timely guidance and support. I truly appreciate their dedication to my financial well-being.
I highly recommend DiMatteo Group to anyone looking for a trustworthy and knowledgeable financial advisor who genuinely cares about their clients' financial success.
- DJ Martin
The statement was provided 7/2/2024 by DJ Martin who is a client. This statement may not be representative of the experience of others and is not a guarantee of future performance or success. For additional reviews, search us wherever local businesses are reviewed.
I highly recommend DiMatteo Group. They are an honest group of caring people with the highest level of integrity and trust. They have been managing my investment portfolio and year end taxes for almost two decades. I always look forward to my meetings with John DiMatteo, where he carefully explains things and discusses ways my wife and I can be prepared for our future in retirement. John is always professional and respectful and is someone that I truly trust with my finances.
If you are looking for a group to manage your finances that cares and treats you more like family than clients, you should set up a meeting and see how they can put your financial mind at ease.
- Paul LaPlaca
The statement was provided 12/23/2024 by Paul LaPlaca who is a client. This statement may not be representative of the experience of others and is not a guarantee of future performance or success. For additional reviews, search us wherever local businesses are reviewed
Dedicated & Dependable
Supporting Our Community
In the spirit of our vision and in honor of our father, grandfather, and founder Tony DiMatteo, we run the DiMatteo Family Charitable Foundation. So far, we’ve raised more than $636,000 for local and national organizations, including Homes for the Brave Female Soldiers/Forgotten Heroes, Spooner House, St. Vincent’s Swim Across the Sound, The Kennedy Center, Valley Community Foundation, Boys & Girls Club of Lower Naugatuck Valley, and Adam's House. We’d love to get you involved and to know what you’re supporting.
Our Broker/Dealer
We are proud to partner with Commonwealth Financial Network®, a Registered Investment Adviser–broker/dealer that helps independent advisors like us serve their clients. As of December 31, 2024, Commonwealth oversees total account assets of $344 billion.
Independent, just like us.
Our partnership with Commonwealth supports our commitment to remain free to act in your best interest, without any pressure to promote proprietary products or strategies.
How Commonwealth helps us help you
Commonwealth offers the scale, stability, and resources that help us deliver the strategies you need. It's that infrastructure–and the expanding wealth of resources it provides–that makes it easier for us to provide you with attentive guidance and the prompt, personal service you expect and deserve.
Keep Exploring
We have a variety of resources to assist in your planning.
Our History: It all started in the '60s
1960-1990
In 1960, Tony and Adeline DiMatteo founded A.A. DiMatteo Insurance in Bridgeport, offering personal insurance and tax services. Their children Loretta and John joined in 1986 and 1988, followed by John's wife Kim in 1990, which marked a shift toward commercial insurance and rapid growth.
1991-1995
In 1991, John DiMatteo launched the financial services department, offering retirement planning and college funding. By 1993, the growing firm moved from a 1,000-square-foot office in Bridgeport to a larger space on Main Street in Trumbull. In 1995, more family members, including Rosemarie, Victoria, and Rob, joined the family business.
2003-2010
In 2003, the firm moved to a 5,000-square-foot office on Bridgeport Avenue in Shelton. In 2005, the DiMatteo Family Charitable Foundation was established in honor of founder Tony DiMatteo, supporting local charities through an annual golf event. Tony passed away in 2010, but his legacy continues through the foundation, the business, and his family.
2016-2022
By 2018, Loretta Lesko and Kim DiMatteo led the insurance department, while John DiMatteo headed financial services and Rose Esposito managed tax and accounting. In 2019, DiMatteo Insurance merged with ACBI, with John DiMatteo continuing to lead financial services. In 2020, Jessica DiMatteo, the second of the third generation, joined the financial team. Adeline DiMatteo passed away in 2022, leaving a lasting legacy.
Today
DiMatteo Group continues to grow by providing high-quality service to clients while still giving back to the community. Built on the hard work of three generations, we remain focused on innovation and excellence. In March of 2025, Michael DiMatteo, the third person of the third generation joined the financial team, bringing a new expertise to the table with his extensive experience in sales leadership/management and cybersecurity.
Let’s connect.
We’re ready to start planning your future whenever you are. Reach out to our team to begin.