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

How to avoid rogue tow truck scams

Bad enough if you are in an auto accident – that’s stressful enough. You might be injured or at the very least, shaken up. Suddenly a tow truck appears on the scene saying they are from your insurance company. While … Continue reading

Focus on Phishing: Take these quizzes to see if you are smarter than the criminals

October is National Cybersecurity Awareness Month, the time of year when cybersecurity experts from government, academia and industry remind us of the importance of safeguarding our digital information and reviewing our online safety practices. One of the most common ways … Continue reading

Fall Home Maintenance Checklist

Fall is time to batten down the hatches before old man winter comes to call. Depending on where you live in the country, your maintenance may vary a bit. While snow can happen in all 50 states, in some states … 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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