133 Defense Highway Suite 214 Annapolis, MD 21401

(410) 777-5390
neal@oldbayinsurance.com
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Local Agents Who Work For You

Actual agents who live in your neighborhood, mutual trust is our number one focus

An Agency that supports their clients current and future needs

Saving money, reviewing policies, help protect their assets and future demands

Your Journey Starts Here

We can help you bridge the gap between where you are and where you want to be.

Auto 

Auto 

In most states, you’re required by law to carry car insurance. 

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Home

Home

What would happen if a disaster struck your home tomorrow?

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Business

Business

As a business owner, every transaction you complete is fraught with peril.

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Personal

Personal

Our insurance is a collection of protective insurance policies for any family. 

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Meet Our Agents

Neal Tatterson

Neal Tatterson

Agent/Owner

Rick Bowers

Rick Bowers

Agent

Sharon Richards

Sharon Richards

Agent

Our Education Center

<p>Did You Know This Fact About Claims Advances?</p>

Did You Know This Fact About Claims Advances?

If a fire forces you out of your home, you can ask for a claim advance.
Learn More
<p>Did You Know This Fact About Winterizing Your Car?</p>

Did You Know This Fact About Winterizing Your Car?

Do you winterize your car? You should consider it.
Learn More
<p>Did You Know This Fact About Foggy Conditions?</p>

Did You Know This Fact About Foggy Conditions?

Foggy conditions make driving more hazardous, but high beams aren't the answer.
Learn More

"Old Bay Insurance company has been great for us. We can always count on Neal to give us whatever information we need right away. I give this company a 5 Star review rating."

- Carolyn Riggins

"Neal is super easy to work with. Great communication. Replies to requests efficiently and professionally. Always tries to find the best policy and value combined for my specific needs. I recommend Old Bay and their personalized service."

- Jo Burkholder

"Working with Neal was great. We had a difficult situation that he managed us thru. He was able to find the right insurance for us and our specific situation. He was diligent, thoughtful, knowledgeable and a nice guy. Highly recommend Neal and Old Bay Insurance."

- David Vogel

"Neal just saved me BIG bucks on my auto policy renwal. I have used Neal Tatterson as my Agent for all my insurance needs for about 20 years now. He is very attentive to service and is concerned with both my expenses and my liability exposure."

- Roger Gerst

"What a great team at Old Bay Insurance. They are responsive, professional and work to get you what you need."

- Christian Dimenna

"I joined Old Bay on the recommendation of my lender when I bought a new house. Im incredibly happy with Neal and everyone else at Old Bay. Wouldn't go anywhere else."

- Jason Guest

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