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

Prepping your RV for summer travel & camping

It’s almost time to hit the road! Before you pack up the family into the RV for a spring camping vacation, take the time to get your winterized RV ready for the warm weather. A thorough once-over will keep your … Continue reading

Time to prep that swimming pool for safety!

Is it too early to think about going swimming yet? We’ve certainly earned warm weather after a snowy, chilly start to spring. Swimming season can’t be far away! But if you own a backyard pool, whether of the in-ground or … Continue reading

Fire extinguishers: What you need to know from A to K

What’s a piece of kitchen equipment that  every cook should have handy and know how to use, but hopes to never need? A fire extinguisher. There are a few different types of fire extinguishers. Some are meant for specialized situations, … 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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