Business Insurance

At Stephen Benjamin Insurance Agency, we know that protecting your business is essential to your success. Our commercial insurance services are crafted to help Massachusetts small businesses safeguard their operations, employees, and assets against unforeseen risks. From liability coverage and property insurance to specialized policies for small businesses, our solutions are designed to be as unique as your business itself.


Business Owner’s Insurance

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Combines general liability and property coverage to protect your business from unexpected risks. Safeguard your assets, employees, and income with tailored coverage designed for small to medium-sized businesses.


Commercial Property & Liability

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Navigating zoning laws and land use regulations requires specialized expertise. We work with developers and investors to secure municipal approvals, handle planning board presentations, and resolve challenges efficiently.


Commercial Auto Insurance

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From site acquisition to final build-out, we provide end-to-end legal support for development projects. Our team anticipates potential hurdles, offering proactive strategies to keep your vision on track.


Commercial Umbrella Coverage

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From site acquisition to final build-out, we provide end-to-end legal support for development projects. Our team anticipates potential hurdles, offering proactive strategies to keep your vision on track.


Surety Bonds

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Ensure trust and financial security with surety bonds. Whether for contractors, businesses, or legal obligations, our bonds guarantee compliance, performance, and financial protection, giving you and your clients peace of mind.


Fidelity Bonds

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Protect your business from employee dishonesty with fidelity bonds. This coverage safeguards against fraud, theft, and embezzlement, giving you financial security and peace of mind.


Builders Risk Insurance

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This coverage safeguards against damage from fire, theft, vandalism, and weather-related events during construction or renovation. Ensure your project stays on track with tailored protection.


Errors & Omissions

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From site acquisition to final build-out, we provide end-to-end legal support for development projects. Our team anticipates potential hurdles, offering proactive strategies to keep your vision on track.

Tailored to Your Business

Have questions about what types of coverage you need?

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.