Your Trusted, Independent Insurance Agency
Your Trusted, Independent Insurance Agency
Serving Maryland Since 1986
Deale & Associates Insurance Agency is a locally owned, independent agency that has proudly served Annapolis and the surrounding Maryland communities for nearly four decades. We specialize in personal and commercial insurance, offering tailored solutions for everything from your family’s home to your small business, recreational vehicles, and more. With a reputation built on referrals, we’re known for treating every client like family—and we work hard to earn that trust with every policy we write.
Our Mission
At Deale & Associates Insurance Agency, our mission is simple: to help you protect what matters most with insurance that’s smart, personal, and rooted in trust. We know insurance can be overwhelming—so we guide you through a sea of options with clarity, compassion, and confidence. As an independent agency, we offer access to multiple carriers and the flexibility to build policies that actually fit your needs.
Our Core Values
Service That’s Personal
We take the time to listen, understand, and tailor coverage to your life—not just your assets.
Relationships That Last
We’re proud to serve families across generations, thanks to the trust and referrals of our clients.
Independent & Honest Guidance
We represent multiple top carriers and recommend what’s best for you—not what’s best for us.
Rooted in Maryland
As a community-based agency, we bring local knowledge and real accessibility to everything we do.
Meet Our Team
Charlie Deale
President
Charlie founded the agency with a focus on personalized service, honest guidance, and building long-term relationships. His leadership reflects the values that have shaped Deale for nearly 40 years.
410-267-5606
Tom George
Associate Agent
Known for his responsiveness and thoughtful support, Tom helps clients find coverage they can feel good about—no pressure, just clear solutions.
410-267-5606
Shannon Stastny
Office Manager
Shannon keeps everything running behind the scenes while providing a friendly first point of contact. She’s here to help with every step of your experience.
410-267-5606
See What Our Clients Are Saying
Incredibly friendly staff, that was knowledgeable and found me the best product for my needs. Deale and Associates saved me over $2,500 for the year. Highly recommended.
– Jay Antonelli
Charlie was very nice to deal with and was extremely responsive to questions and requests. He provided multiple choices of insurance for our requirements and we were able to make an informed choice. I would recommend his services wholeheartedly.
– Snehal Shetye
Deale & Associates is a great local agency. I have worked with them for many years and find that they are always looking for the best policies for their customers. Great to work with!
– Derek Heiss
All my insurance has been through Charlie since I started driving at 16 years old. I have never found the need to change that. Charlie has always reached out to me when he could save me money on my insurance and provided me with the best overall options available.
– Mike Barnhart
When I call with a question, I am met with a quick, respectful response. If I am wondering if I have the best coverage, Tom George takes the time to listen to my concerns, then talk with me about the coverage best suited to my needs. I am very happy with Deale Insurance Office!!
– Cherry Miloe
Auto, Home & Life Insured with Charles Deale & Associates for 20+ years now... Great staff with excellent customer service. I will continue to refer my family and friends for all their insurance needs. Give them a call today!
– Brittni Leizear
Late one Sunday afternoon in July 2011 a tree fell through the roof of our newly rebuilt house. I left a voice message for Charlie Deale and within the hour a whole crew arrived to protect the house and start the clean-up. This rapid Sunday afternoon response was beyond our expectations and highly appreciated.
– David Huggins
Incredibly friendly staff, that was knowledgeable and found me the best product for my needs. Deale and Associates saved me over $2,500 for the year. Highly recommended.
– Jay Antonelli
Charlie was very nice to deal with and was extremely responsive to questions and requests. He provided multiple choices of insurance for our requirements and we were able to make an informed choice. I would recommend his services wholeheartedly.
– Snehal Shetye
Ready for Coverage from People Who Truly Care?
Whether you’re insuring your car, your home, your business — or all three — our team is here to guide you every step of the way. We take the time to understand your unique needs, clearly explain your options, and deliver the kind of personal service that makes you feel like part of the family.
Request a free, no-obligation quote today and experience the difference of working with a team that genuinely cares about you and your future.
