Navigating a Sea of Policies Since 1986.
Insurance That Treats You Like Family Because to Us, You Are.
Protection That’s Personal
Your car gets you where you need to go—our job is to make sure you're protected on the way. From daily commutes to weekend getaways, we offer policies that fit your lifestyle and budget.
Whether it's your first home or your forever home, we help you protect it with personalized coverage built around Maryland living.
From Main Street shops to local contractors, we help Maryland businesses protect their people, property, and livelihood—so you can stay focused on what matters most.
Boats, RVs, and more! Enjoy your getaways with confidence, knowing you’ve got the right protection behind you.
From back roads to coastal rides, we offer coverage that rides with you—so you can hit the road with confidence.
Tomorrow isn’t guaranteed, but peace of mind can be. Let’s build a plan that protects the people you love when they need it most.
Locally Rooted. Regionally Licensed. Always Personal.
Based in Annapolis, Deale & Associates Insurance Agency has proudly served Maryland families and businesses since 1986. As a locally owned, independent agency, we don’t push one-size-fits-all coverage—we guide you to the right policy for your life, home, or business.
Licensed in
Maryland, Virginia, Delaware, and Florida, we combine deep community ties with access to top insurance carriers. The result? Smart solutions, clear guidance, and the kind of service that earns referrals—and trust—for generations.
Why Clients Trust and Recommend Us
Clients come to Deale—and stay with us—because we offer more than just insurance. They trust us because:
- We’re independent and work for you, not the carriers.
- We listen and understand your unique needs.
- We’re local, accessible, and here when it counts.
- We believe in personalized, long-term relationships.
That’s why most of our new business comes from word-of-mouth—and why we treat every referral like family.
See What Our Clients Are Saying
Abhay Chaudhari
"Charlie was great to work with. You reviewed my current insurance policies and was very straight-forward with what policies were already good with good rates and what he could offer for some of my higher premiums. The office communication was great and I opened up Home Insurance and Umbrella policies with them. Highly recommend them for your insurance needs!"
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Gloria McJilton
"My experience with Deale & Associates has consistently been positive. Mr. Deale and his staff are very knowledgeable, courteous and always professional. I especially like how proactive and prompt they are in reaching out to their customers. It’s reassuring knowing that all of my insurance needs are being met!"
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Jennifer W
"Deale & Associates have been my insurance provider for over 30 years. The insurance products the agency has offered to my family over those years has always been as comprable or better than all the other advertised competitors on the market. What makes Deale & Associates stand out is the superior customer service that I have rec'd over that time. I know that no matter the size of my account or my concern I receive pleasant helpful service and follow up. Thank you."
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Eric Ohrvall
"We recently asked Charlie Deale to be our insurance agent after becoming dissatisfied with our previous insurance company. Charlie very quickly demonstrated what customer service means to Deale& Associates by coming to our home to assess what we needed for our vehicles and our home, clearly explained our options an cost an provided us with written proposals to review. He improved our coverage an reduced our cost. We highly recommend Deale & Associates."
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Todd Maxwell
"Switched to Deale after moving from NC based on a family recommendation and haven't been happier. They are very professional and responsive. You get the feeling that they have your interest in mind and not always the insurance company which is refreshing. Best insurance company I have dealt with!"
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Let’s Build the Right Coverage, Together.
Whether you're looking for auto, home, life, or business insurance — or a customized bundle designed just for you — our dedicated team is here to guide you every step of the way. We’ll take the time to understand your needs, walk you through your options clearly, and help you feel confident that you’re covered where it matters most. Let’s protect what matters to you, together.
