Whether you need insurance for your primary or secondary home, condominium, or mobile home or need renter's insurance, we can provide superior insurance packages that are unequaled in the industry. We offer competitive insurance rates for auto, motorcycle, ATV, RV, boat, flood, commercial property, general liability, commercial auto, workers comp, term life, and universal and whole life policies.

Bundling your insurance policies under one insurance carrier can help you realize cost savings in multi-policy discounts, as well as provides the convenience of having everything under one roof.

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Meet the Team Report

Principle agent Jerry Judge started in the insurance industry in 1990. He has owned Bayside insurance since 1998. When not managing the day to day operations at Bayside Jerry enjoys offshore fishing on his boat Double J in the summer and hunting in the winter. Jerry's two daughters have recently graduated college and have started careers in engineering.

About Report

Since 1977, Bayside Insurance has been providing the Upper Eastern Shore with high-quality insurance products customized to fit a variety of insurance needs. With convenient locations in Chester and Easton, Maryland, Bayside Insurance offers experienced insurance agents who know the communities they serve.

Auto Report

Whether you have a new or antique automobile, truck, motorcycle, ATV, Snowmobile, Golf Cart or RV, or are insuring a new driver in your family, we can help you find the right coverage for you. Understanding the nuances of your policy can provide you with the reassurance that your insurance policy is customized for your individual needs, family circumstances and state requirements.

Homeowners Report

Whether you need insurance for your primary residence, secondary residence, or seasonal property - we have a variety of homeowner insurance products to offer. Protection against property damage caused by tornadoes, fire, theft, wind, and flood is important in the changing climate we live in today. To be sure your home is properly protected, our agents will meet with you to review your needs thoroughly, explain your options, and help you to understand how the coverage you select can be applied in various situations, including adding living expenses, sump pumps, personal liability, identity recovery, and service line protection.

Athena Papaporfiriou

May 06, 2020

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Got us the best price on both auto and homeowners insurance!

Eleftheria Garas

Dec 15, 2019

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Peter is amazing! The big insurance companies don't come close to the service you will get from this office, not to mention I SAVED an unbelievable amount of money. Try them out if you like keeping your money in your pocket and not GEICO OR ALLSTATES!

Angeliki Mikedis

Oct 25, 2019

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Very helpful service - I would definitely recommend them. Angela got me a great home insurance for a better price than what I had before. And she made the process very easy.