A family firm. Guidance for generations.

Financial planning begins with understanding the people behind the decisions.

At DiMatteo Group Financial Services, we help you prepare for retirement, navigate life’s changes, and consider the people and priorities connected to your financial future.

Meet Our Team

As a multigenerational, family-owned firm, we bring a personal perspective to that work. We understand that your decisions may affect your household today, loved ones who need support, and generations still to come.

From Shelton, Connecticut, and Redington Shores, Florida, we build relationships that grow with you.

A Relationship You Can Turn To

When an important question comes up, we want you to feel comfortable calling us.

You may be approaching retirement, making a decision about your business, or helping a family member through a transition. We listen, explain the financial considerations, and help you identify practical next steps.

Our six-step financial planning process gives those conversations structure while keeping your circumstances at the center.

Some decisions benefit from several perspectives. When appropriate, we help you connect with professionals and resources relevant to your needs.

Retirement Planning With Your Whole Life in View

Retirement planning anchors our work, but your retirement decisions rarely stand alone.

How much you save, how you invest, the support you provide to family, and your plans for a business can all influence what comes next.

Our financial planning services help you consider those connections, understand your options, and make informed decisions. As your priorities change, we revisit your plans together.

Explore Our Services

Our Values in Action

01

Always Growing

Your needs evolve, and so do we. We keep learning and improving our knowledge, service, and approach so we can bring thoughtful guidance to your questions.

02

Treat People Like Family

We take time to listen, respect your individual circumstances, and follow through. To us, treating people like family means showing care through consistent attention.

03

Serve Generously

We share our time, knowledge, relationships, and resources to support clients and contribute to our community.

04

Proactive Guidance

We look ahead, raise questions, and help you prepare for decisions. Clear communication and thoughtful follow-through are central to how we work.

05

Enjoy the Journey

Your financial plan supports a life being lived today. We make room to recognize milestones, celebrate progress, and appreciate the relationships built along the way.

Our Family Story

Connecticut Roots

Our family business began in 1960, when Tony and Adeline DiMatteo founded A.A. DiMatteo Insurance in Bridgeport, Connecticut.

Financial Planning Becomes Part of Our Work

In 1991, John DiMatteo established the financial services department, expanding the family’s work to include retirement planning and college funding.

A Continuing Family Commitment

Over the years, additional family members joined the business, bringing new perspectives and experience. That continuity shapes how we think about relationships, responsibility, and planning across generations.

Today, our leadership team carries that perspective into our work with families and business owners in Connecticut, Florida, and beyond.

Giving Back Across Generations

Serving generously extends into our community.

Established in 2005 in honor of founder Tony DiMatteo, the DiMatteo Family Charitable Foundation supports charitable organizations through fundraising and community involvement.

It is one way our family continues its commitment to helping others and invites others to take part.

Explore Our Community Giving

Financial Guidance in Connecticut and Florida

Wherever you are in your planning journey, we start with what matters to you.

Our locations in Shelton, Connecticut, and Redington Shores, Florida, support our relationships with individuals, multigenerational families, and business owners.

Connecticut

1000 Bridgeport Avenue, Unit 506
Shelton, CT 06484

Florida

17715 Gulf Boulevard, Unit 601
Redington Shores, FL 33708

Phone & Email

Phone: 203.924.5420
Email: info@dimatteofinancial.com

Let’s Start With Your Questions

You don’t need a finished plan to start a conversation.

Tell us about the decisions ahead, the people you’re planning for, and what you hope your next chapter will look like. We’ll help you explore your options and discuss how we can support you.

Schedule a Conversation