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

Spooky guide to New England Halloween happenings

Get your fright on! Between now and early November, there’s no shortage of spooky, haunted happenings to scare and delight you. Whatever your age – young, old or in-between, there is something for you in our guide. We’ve selected a … Continue reading

Have a fireplace? Time to clean that chimney!

What’s better on a chill winter night than a crackling fire in the fireplace? But if you have a fireplace, it’s extremely important that you conduct ongoing maintenance — and it’s a good time to do that now, before the … Continue reading

Don’t fall for flu myths: get your flu shot early

We tend to think of the flu as a winter illness, but October is the start of flu season in the United States, continuing on through May and generally peaking in January or February. It’s not too early to think … 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.

Get directions

bw-map