Calvin Sheets Insurance Insider and Senior Advisor

Founded in 1983 by Calvin Sheets, Sheets Insurance began as a Captive Nationwide Insurance agency in Bear, Delaware. Calvin, a true “scratch agent,” built the business from the ground up, guided by one simple but powerful principle: treat every client like family. Quickly becoming an expert through his unwavering commitment to trust, transparency, and building strong, lasting relationships became the cornerstone of the agency’s growth and reputation in the community utilizing insider knowledge.

Family owned office Located in Bear, Delaware. Sharing insurance Insider knowledge with clients since 1983.

Over the years, Calvin’s dedication earned the agency a loyal client base and a strong presence across Delaware. By putting people before policies, Sheets Insurance became known not just for coverage solutions, but for exceptional service and a personal touch that larger companies often lack.

In 2020, the agency made a major transition from a Captive Nationwide agency to an independent broker. This shift opened the door to partnerships with a wider range of trusted providers, giving clients more choices, flexibility, and customized solutions. No longer limited to a single company’s offerings, Sheets Insurance could now provide multiple quotes, ensuring clients always had the coverage that fit their unique needs. This evolution helped the agency expand its services, strengthen relationships, and solidify its reputation as a dependable, client-focused independent agency.

Head Shot, Kyle Sheets Insurance Insider and Expert

In 2024, leadership passed to Kyle Sheets, who continues to uphold the agency’s tradition of integrity, personalized service, and a client-first philosophy. Kyle’s vision combines the time-honored values of a family-owned business with a modern, forward-thinking approach. Under his guidance, Sheets Insurance maintains its local “Mom and Pop” atmosphere, while leveraging industry Insider knowledge, technology, and independence to outperform larger corporate competitors.

Today, Sheets Insurance is a trusted, community-focused agency serving families across Bear, Middletown, Townsend and Smyrna Delaware. Backed by over four decades of experience and a Team of dedicated, knowledgeable professionals, we combine ethical service with a client-first approach. Our team’s expertise and commitment ensure that every client receives personalized guidance and protection that truly fits their needs, helping generations of Delaware residents safeguard what matters most.

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See Why Our Customers Love Us

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Laura profile picture
Laura
24 September 2026
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I can’t say enough about sheets! They do a great job of shopping around for the best policy at an affordable price. Today I worked with Jen and she is amazing. She explains everything very clearly even through email which is amazing because I am unable to talk on the phone at work. She was able to explain everything to me in detail via email in a way I could understand. Take all the stress out of insurance shopping and contact Jen at sheets today!
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Chanelle Spotswood
23 September 2026
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I recently worked with Jennifer P again while switching my auto insurance to Geico, and once again she was absolutely wonderful to work with. She was incredibly helpful, patient, transparent, and responsive throughout the entire process. She took the time to answer all of my questions and made the transition so easy for me. I truly appreciate Jennifer’s continued help and would highly recommend her to anyone looking for an agent who genuinely cares about her customers!
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Violet Spring
21 September 2026
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Jennifer was very helpful
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Amy Roberts profile picture
Amy Roberts
17 September 2026
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Christopher Phillips was extremely helpful and knowledgable. He helped me find a better price for auto and home insurance and it was easy to switch from a company I had been with since 1985. Thanks Chris! I will recommend you to others.
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Ylana Wesley
14 September 2026
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Jen is always on top of getting me the best rates and coverage to support my needs.