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(410) 777.5390
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Our Locations

Old Bay Insurance Agency - Main Office

133 Defense Hwy, Suite 214
Annapolis, MD 21401
Main office: 410-777-5390
Fax: 410-774-5240

Office Hours:

Mon: 9:00 AM - 5:00 PM
Tues: 9:00 AM - 5:00 PM
Wed: 9:00 AM - 5:00 PM
Thurs: 9:00 AM - 5:00 PM
Fri: 9:00 AM - 5:00 PM
Sat: Closed
Sun: Closed

Old Bay Insurance Agency - Satellite Office

2002 Annapolis Mall
Annapolis, MD 21401
Main office: 410-777-5390
Fax: 410-774-5240

Office Hours:

Mon: 10:00 AM - 9:30 PM
Tues: 10:00 AM - 9:30 PM
Wed: 10:00 AM - 9:30 PM
Thurs: 10:00 AM - 9:30 PM
Fri: 10:00 AM - 9:30 PM
Sat: 10:00 AM - 9:30 PM
Sun: 11:00 AM - 6:00 PM

Our Providers

Delivering home, auto, and business insurance in Annapolis and Severna Park, MD


We’re an independently owned and operated agency in Annapolis, Maryland and we serve individuals, families, and businesses with comprehensive products and personalized services.  We’re professional, affordable, and strong and are committed to giving each client the best insurance experience possible. 


We provide solutions throughout Maryland, Virginia, and the District of Columbia and we’ve served these areas for many years.  To all of our clients and potential clients in these areas we offer the greatest selection of coverage and policy options.  We’re able to do this because we partner with different carriers.  The options that these carriers help us provide include programs for business and for personal lines like home, auto, and life.  For specific industries we have specially-designed programs that include construction and trucker’s insurance.  In particular, for any business, we have a commercial auto policy option that provides the protection needed. We are also happy to provide bonds (either Fidelity or Surety) for any and all of our commercial clients. 


In order for us to serve clients best we get to know clients and we support these clients throughout the lives of policies.  We manage risk and claims, regularly monitor policies, and are fully available.  This ensures that insurance experiences are easy and valuable.  Our approach is very hands-on and exhaustive, and as a result we provide great value.


Please contact us or give us a call to learn more.  You can request a quote to get started.


Questions about the Annapolis MVA? Check out their helpful YouTube channel or visit them online.



Phil ROCKS! He not only saved us a TON of money on our insurance but is friendly & helpful with any & all reminders & questions! You will not be disappointed! Thank you for all that you do for us!
- Megan Rosendale
Neil Tatterson is very knowledgeable and attentive. Going with Old Bay Insurance saved my family a bunch over our previous insurer.
- Sean Lyon
Neal is Amazing! I have my business insured with him As he helps with all aspects and his speed of response on answers to questions and documents needed is quicker then ever expected and always appreciated. When running a business it is nice to have someone to count on!
- Daniel Reall
For several years I was looking for an insurance company. I found Neal and Old Bay Insurance and gave them a shot. They took my business. Over the years there was a choice for us to make. Stay with Neal and change my carrier, or stay with my carrier and let Neal go. We considered and decided to stay with a local business , Old Bay Insurance. We have been satisfied with this decision. and now Endorse Neal and Old Bay Insurance. Our feelings are work with local business. We consider where our money goes. And how it is used. We want local companies to develop and local lives to prosper. And from this though process today years later we are happy with our choice of insurance provider. Of note Neal has grown with us in his customer service. Which is important to us. We do endorse Old Bay Insurance and Neal Tatterson.. And are satisfied with their work and product.
- Terry Black
Neal and his team are so wonderful to work with, you can even text with them if you need anything. They were able to lower my auto insurance rates, and do the same for my brother and a good friend of mine - all with great coverage. Highly recommend them for anyone looking for an independent insurance company.
- Niki Rogers
Neal Tatterson reviewed my insurance coverage and was able to lower my cost by 50%!!! Old Bay Insurance Agency has amazing customer service. I will be referring all my friends and family to Neal and his team!!
- Leticia Bustamante Guzman
Neal is awesome - and he looks so suave in his picture. Kinda like a secret agent, agent.
- Erik Lytikainen
Neal was a great help switching our insurance and saved us about $400.00 this year!! We highly recommend Old Bay Insurance!
- Jennifer Tollberg-Van Breevoort
Neal did a great job with helping my daughter switch her auto to a lower rate and got her homeowners insurance. All was done fast and precise.
- Mary Stokes
I just wanted to drop you a short line and thank you for always being their for our families' insurance needs. First off, you have been our agent through many transitions and challenging times, whether it be a car accident or just questions about how to proceed next. You have been our agent for about 15 years and I would never change insurance agents, as you are the best!!! You always seem to have the answer to whatever issue comes up and the resources and ability to solve it quickly. Case in point, when I called yesterday to ask you a question about the MVA and a recent letter they had sent me, you said let me check it out on the internet and then call them directly. Within twenty minutes you called me back to say that it was all worked out and that it was just a mistake in their computer file for our car. That saved me the potential headache and aggravation with having to make a personal visit to the MVA to resolve the situation. Thank you for that and so many other situations that you have helped us out on through our long relationship. The other thing that I have to say is that working with Allied Insurance has been quite wonderful as well. I always liked Erie insurance too when we were with them for all those years. I have to say though, the ease of contacting them and paying my bill or talking to an agent on the phone, has always been easy and pleasurable and I like them even more than Erie. You teamed up with Allied, makes a pretty amazing combination for anyone's insurance needs!!! Thanks as always and peace to you and your family.
- Chris Luzier
I've know Neal Tatterson for over 20 years. Always been a pleasure doing business with him. He is knowledgable about all aspects of insurance. I would highly recommend him as an agent.
- Albert Lee
Neal Tatterson and Old Bay Insurance have been fantastic to work with over the years. Neal is always prompt in his replies to my requests and always finds ways to get my family exactly what we need for our insurance needs. I highly recommend Neal and his company!
- Joe Burcham