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.


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.


Consumer Insurance Blog

Post-Thanksgiving shopping extravaganzas – a few safety tips

Once upon a time, we all celebrated Thanksgiving, watched a few football games and had a leisurely post-holiday weekend. Now it’s a shop-til-you-drop extravaganza that extends over 5 or 6 days – yikes!  We offer a rundown with some consumer … Continue reading

Best & Worst Thanksgiving Driving Times

If you’ll be driving to visit friends or family on Thanksgiving, you’ll enjoy remarkably low gas prices. Gas Buddy reports that the national average per gallon is $2.139, down .73 from last year’s average of $2.876! And last year, we … Continue reading

Vintage insurance advertising!

Photoshop has nothing on the photo montage specialists of the 1800s, who were adept at “trick photography.” Witness this historic Civil War era image title “Union Commanders” from the Library of Congress. Linton Weeks of NPR’s history department took a … 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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