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

Earthquakes, floods & other catastrophes: Could they happen here?

It’s sad and shocking to see the devastation in Italy from the recent earthquakes in Italy and the widespread flooding in Louisiana. Natural catastrophes are always difficult, particularly when there is heavy loss of life and when the devastation is … Continue reading

Back to school toolkit for kids of all ages

It’s getting to be that time of year… back-to-school season! Over the years, we’ve posted lots of advice for parents and students of all ages. In this post, we’ll offer some of our best back-to-school posts, with a few new … Continue reading

Beat the Extreme Heat Tools!

With oppressive heat and humidity in the forecast for the Northeast today and through this weekend, we’ll all be looking for ways to beat the heat. If you’ll be working or playing outside, it’s really important to slow down, take … 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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