Personal & Family Insurance

The unexpected happens – make sure you and your assets are well protected. The experts at Leonard Insurance Agency tailor coverage to meet your exact needs.

Business & Commercial Insurance Products

Trust the professionals at Leonard Insurance Agency to assess your company’s needs and provide the best products at the best prices. We have a full range of coverage to protect you and your business so you can focus on what matters most.

About us


Leonard Insurance Agency is an independent insurance agency based in Osterville, MA. For more than a century, we’ve been helping our neighboring Cape Cod businesses, families and individuals to meet their insurance needs. Whether it’s auto insurance, homeowners, boat, or business insurance, we understand your needs because we understand the way you live. And because we have priority access to dozens of premier insurance companies, we can find the right product at the right price.

Claims Reporting

If you have a claim during normal business hours, please call us – we are happy to help. But if you prefer online reporting, or if you should need to file a claim during nights, weekends, or holidays, here are links to online claim reporting services for our insurers.

Tools

These tools and links are provided as a service to our clients. We are happy to serve you should you have any questions about your policies, your coverage, or assessing your needs – give us a call!

Online bill payment

Want to pay your insurance bills online? These links are to online bill payment options for our insurers.

News

Consumer Insurance Blog

Car thieves are just driving away with our cars for the darndest reason!

We’ve all misplaced our car keys at one point or another, but are people getting more forgetful? That would appear to be the case if we review the recent report that the National Insurance Crime Bureau (NICB) issued on car … Continue reading

Thinking of a side hustle? Check with your insurance agent

Today, it seems like everybody’s got a side hustle, which is essentially just a fancy rebranding of what used to be called moonlighting. But today’s moonlighting often comes with a twist …. these gigs often involve using your personal car … Continue reading

Your annual reminder: Any dog can bite

This week is Dog Bite Prevention Week and the US Postal Service would like to remind you that although there are about 78 million good doggies here in the U.S., “any dog can bite.” They should know. Their carriers suffer … Continue reading



Contact us

Contact us

Leonard Insurance Agency, Inc.

683 Main Street, Suite B
Osterville, MA 02655

Telephone: 508-428-6921
Fax: 508-420-5406
Email: To help us meet your needs and get your query to the right place, please use the e-mail form below.

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