A TrustedChoice.com recommended local independent insurance agency, with elite-level expertise, is here to assist you with your insurance needs. Your protection is their priority. Recommended Local Agency
Old Bay Insurance Agency, Inc.
  • Business
  • Home
  • Auto
  • Life

Old Bay Insurance Agency, Inc.

Independent Insurance Agent in Annapolis, MD

About us

From Steamed Crabs to Homeowner's Insurance Old Bay's Got You Covered

Thanks to the leadership and expertise of Neal Tatterson, Owner and Agent - Old Bay Insurance is celebrating 30-years of serving the Annapolis, Anne Arundel County, and all of the Maryland areas. Our company has had the distinct pleasure of working with thousands of families, individuals, and young adults for everything from their first auto insurance to whole life policies. Our team of insurance agents make themselves available to policyholders, not just to discuss the product, but also to educate policyholders on the product as it relates to their finances and lifestyle. Walk into our office and you'll be walking into the room with a combined 60+ years of insurance experience. Our approach to insurance? It's all about the relationships, because who better to be friends with than someone who knows insurance inside and out? Plus, we understand you have things to do, and although insurance may be high on your priority list - it may not be high on your "favorite things to do" list.

Personal Lines insurance professionals

Ask me about these types of insurance...

Having the right car insurance is so important, even more important is understanding all the ins and outs of your coverage to help protect you.

Request an automobile insurance quote

Get multiple quotes on your homeowners insurance with one phone call. Let an independent agent shop for you.

Request a homeowners insurance quote

An independent insurance agent will walk you through top umbrella policy options to make sure you have the proper coverage to tackle above and beyond claims.

Request an umbrella insurance quote

States we serve

  • DC
  • Delaware
  • Florida
  • Maryland
  • Pennsylvania
  • Virginia

Our insurance coverages

Personal insurance coverage

  • Automobile
  • Boat
  • Builders Risk / Construction
  • Collectible Auto
  • Condo
  • Flood
  • Home
  • Landlord
  • Motorcycle
  • Personal Watercraft
  • RV / Motorhome
  • Renters
  • Umbrella

Business insurance coverage

  • Business Owners Package (BOP)
  • Business Vehicle
  • General Liability
  • Property

Life & Annuities coverage

  • Annuities
  • Life

Recommended insurance company partners

Other companies we work with:

Agency Insurance Company, Chartis Property Casualty Company, Chubb, Cumberland Mutual, Donegal Mutual Insurance Company, Farmers of Salem, GEICO, Maryland Automobile Insurance Fund, Mutual Benefit Group, National General Insurance (GMAC), Penn National Insurance, PersonalUmbrella.com Insurance, RPS, Scottsdale Insurance Company, State Auto, The Hanover Insurance Group, The Hartford, US Assure, United States Liab, Utica First Insurance Company, Utica National Insurance, Vindati

Old Bay Insurance Agency, Inc. Team

Neal Tatterson - Owner
Neal Tatterson
Owner
(410) 777-5390
Vickie Holder - Personal Lines Manager
Vickie Holder
Personal Lines Manager
(410) 777-5390
Dollie Kreger - Agent
Dollie Kreger
Agent
(410) 777-5390
John Giovingo - Agent
John Giovingo
Agent
(410) 777-5390

Old Bay Insurance Agency, Inc. Reviews

Average based on 4 reviews Leave a review

Customer Reviews

September 10, 2025

My experience with Old Bay insurance was top notch. I was handling my mothers insurance and my dealings with John were so smooth. He took care of my mother's insurance and found her the best rates he could. Very impressed with your company.

September 10, 2025

Neal was amazing and responsive when I needed some help on the road. It seems to be the culture of the agency as my old agent was every bit as helpful. I appreciate them!

September 10, 2025

Fair prices and easy to work with.

September 10, 2025

Old Bay was not only the first agency to take our call rather than sending us to voice mail. They were very helpful arranging for insurance coverage in time for our closing, even though most companies would not insure a waterfront property with a 20 year old roof. Old Bay arranged for our insurer to provide coverage with an adequate amount of time to replace the roof after closing on then purchase. They even recommended a roofer who did an excellent job and was more reasonably price than many of the estimates we received. Many thanks to Old Bay for helping to welcome us to our new home and community.

Our Commitment to Transparent and Trustworthy Reviews

We prioritize honest feedback from our clients to assist future customers in making well-informed decisions. Our review section showcases authentic experiences from real customers. When a less-than-positive review is submitted, we share it with both the agent and the reviewer to foster collaboration and improvement based on constructive feedback. We also moderate reviews to remove inappropriate content or spam, upholding a high standard of trust and transparency.

RECOMMENDED INSURANCE COMPANY PARTNERS

Old Bay Insurance Agency, Inc.

From Steamed Crabs to Homeowner's Insurance Old Bay's Got You Covered

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