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

Do you fly in the U.S.? You might need REAL ID by October 1, 2020

Do you fly on commercial airplanes for work or for pleasure in the U.S.? Do you regularly visit military bases or secure federal facilities? If so, this is the year you will need to have either a REAL ID-compliant license … Continue reading

Quick best practice tip for your 2020 financial and legal documents

It’s a new year – time to get in the habit of changing the year that you use when you write a quick check or date documents. But there’s another habit you should alter this year, according to police and … Continue reading

Favorite blog posts for 2019 and all-time

Here are the Top 10 Blog Posts that were reader favorites in 2019 1. Never plug a space heater into a power strip 2. New Massachusetts hands-free driving law to go into effect in February 2020 3. Update your life … 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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