Meet Our Team
Meet Our Team

Diana Halsey

Insurance Consultant

60 Burlington Mall Road, Suite 111
Burlington, MA 01803

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Phone: 781-942-1583

Fax: 774.321.3453

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Diana brings over 35 years of insurance knowledge and experience to her Bearingstar clients. Since returning to sales in 2009, Diana has relied on her deep understanding of personal, commercial and life insurance in order to provide her customers with the support and service they need.

Being a member of the Reading Chamber of Commerce allows Diana to connect with her customers and community. She has held the designation CIC (Certified Insurance Counselor) since 1996, and also belongs to the Society of Certified Insurance Counselors and has won numerous awards for sales and sales management over the years.

Diana is a graduate of Simmons College in Boston, MA. She lives in Reading, MA and enjoys spending time with family, watching baseball and reading.

Reach out to Diana to start your insurance quote

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Bearingstar 2025 Charitable Fund Highlights image

Our Year in Giving Back: 2025 Charitable Fund Highlights

At Bearingstar, giving back is more than a tradition. It is part of who we are. Through the Bearingstar Insurance Charitable Fund, employees across Massachusetts and Connecticut continue to uplift the communities we call home. Whether we are volunteering at local events, supporting families in need, or donating to organizations making a real difference, we are proud of the impact our team helped create this year.

Image of a New England home with a storm brewing above

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Severe storms hit our area all the time, but not many of them are a match for the strength and breadth of a hurricane. These forces of nature typically span at least 300 miles and arrive with sustained winds of 157 mph or more. Even communities a good distance from the eye of the hurricane…

Image of four teenage girls leaving home for school

How Much Umbrella Insurance Do You Need?

In Connecticut, where high home values, busy roadways, and a strong boating culture increase liability risks, a personal umbrella policy offers critical extra protection. If a claim exceeds your home, auto, or watercraft policy limits, umbrella insurance steps in to help safeguard your assets.

Visit the Blog