If it matters to you, it matters to us.


Umbrella Insurance

By purchasing an umbrella policy, avoid financial ruin.


Fine Arts/Collectibles Insurance

As a collector, you would consider some items in your collection priceless.


Car Insurance

It’s about more than just the car – it is a passion.

Why Toole Insurance? Why Should you work with us?

For that matter, in a world of mega-insurance companies like Geico and Progressive, what could a small, independent agency possibly offer?

Personal Service. Real People. Local Expertise.
We have been in business since 1939 and we are currently licensed in more than 30 States.

I Need Business Coverage

I Need Personal Insurance

Fine Art Insurance

MAIA renews five-star rating for
Toole Insurance Agency

The Massachusetts Association of Insurance Agents has renewed its Five Star Agency Designation for L.V. Toole Insurance Agency of Lee and Lenox. Toole has been a five star agency since 2002, and continues to demonstrate excellence in the five imperatives associated with the designation: customer focus, management/leadership, human resource, product and process, and future success initiatives.

MAIA awards the Five Star Agency Designation to independent agencies that go through a vigorous review based on key criteria that affect an insurance agency and how it operates. Upon earning a qualifying score, an agency becomes a Five Star Agency Designee and must go through an intensive review process every 3 years.