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

DUI Laws, Insurance Rates, and Interlock Devices

Don’t drive drunk. Don’t drive while impaired. Just… don’t. It’s sound advice you’ve heard a million times before. It’s common sense. And it’s one of the best ways to avoid taking a significant hit to the wallet when it comes … Continue reading

Apartment dwellers: Don’t miss out on the protection that renters insurance offers

Great, you have a great new apartment. You’ve thought of everything – the mover, the new furnishings, the utilities. You’ve got everything covered. Or do you? Too few people are taking advantage of one of the most affordable and practical … Continue reading

Handling pet fears in thunder & lightning storms

When the thunder roars and the lightning crackles, there’s a primal satisfaction in being snug and dry beneath a stout roof surrounded by sturdy walls. And that’s just as true for your pets as it is for you and the … 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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