Personal Insurance

Our personal insurance services are designed to provide peace of mind, helping to ensure that you, your family, and your assets are covered. Whether it's safeguarding your home, car, or personal belongings, or planning for life's uncertainties, we offer a range of customizable insurance solutions tailored to meet your unique needs.

Auto Insurance

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From everyday drivers to classic cars and motorcycles, we provide coverage that keeps you protected on the road. Get the right policy for your vehicle today.

Home Insurance

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Protect your home—whether it’s a house, condo, rental, AirBnB, or mobile home. We can even help protect your home when vacant. Our policies can safeguard your property and belongings, giving you peace of mind where it matters most.

Life Insurance

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Ensure your loved ones are financially secure with a life insurance policy tailored to your needs. Plan for the future with coverage that provides lasting peace of mind.

Umbrella Coverage

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Extra protection when you need it most. Umbrella insurance extends your coverage beyond standard policies, helping shield you from costly liability claims and unexpected events.

Boats, RVs, & Toys

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Enjoy adventure with confidence. From boats and jet skis to RVs and ATVs, we offer specialized coverage to keep your recreational vehicles protected wherever the journey takes you.

Pet Insurance

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Unexpected vet bills can be costly. Our pet insurance plans help cover medical expenses, ensuring your furry family members get the care they need without financial stress.

The Independent Advantage

Why work with Stephen Benjamin Insurance?

85 Years of Trust and Commitment

Four generations strong, we’ve earned our community’s trust by delivering reliable coverage and personalized service since 1939.

Local Roots, Lasting Relationships

As a family-run agency in Sutton, MA, we’re deeply invested in the well-being of our neighbors—because your future is our future.

Tailored Coverage That Makes Sense

From auto and home to life and small business insurance, we match you with policies that fit your life, your needs, and your budget.

Real People, Real Answers

You’ll never get lost in a call center here. We take the time to listen, explain your options, and make insurance feel simple—not stressful.