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Find Commercial Insurance Agents Near You in Winchester, MA

Looking for a commercial insurance agent in Winchester? Review the directory below to compare your options.

12 agents listed
Updated May 2026
Winchester, MA
Important: Listings are compiled from publicly available sources and have not been independently verified by BeforeInsuranceUSA.com. We do not endorse any agent or guarantee outcomes. Verify licensing and disciplinary status with the Department of Insurance of Massachusetts before hiring.
Showing 12 commercial insurance agents in Winchester, MA Listings are displayed in no particular order and are not ranked by BeforeInsuranceUSA. Order does not constitute a recommendation or endorsement of any agent.
Scotti Insurance Agency
19 Mt Vernon St, Winchester, MA 01890
(781) 729-9200 scottiinsurance.com
Saltmarsh Insurance Agency
751 Main St, Winchester, MA 01890
(781) 729-4615 saltmarshinsurance.com
John A Pierce Insurance Inc
934 Main St, Winchester, MA 01890
(781) 729-8770 johnpierceinsurance.com
Admiralty Insurance Agency Inc
2 Central St, Winchester, MA 01890
(781) 721-5500 admiraltyinsurance.com
W Allan Wilde & Son Insurance Agency, Inc.
887 Main St #1911, Winchester, MA 01890
(781) 729-1400 wildeinsurance.com
Horace Mann Insurance Co
895 Main St, Winchester, MA 01890
(781) 368-9029 agents.horacemann.com
Furey Insurance
28 Church St #8, Winchester, MA 01890
(781) 721-5758 fureyins.com
BARRY FREEMAN
895 Main St, Winchester, MA 01890
(781) 368-9029 barryfreemaninsurance.com
Barry & McHugh Insurance Inc
10 Skillings Rd, Winchester, MA 01890
(781) 729-6600 barryfinn.com
Jay M Finn Insurance
10 Skillings Rd, Winchester, MA 01890
(781) 729-5724 barryfinn.com
Ducey Insurance Agency
10 Skillings Rd, Winchester, MA 01890
(781) 235-6795
Black Horse Insurance
175 Washington St # C24, Winchester, MA 01890
(781) 729-1164 blackhorseinsurance.com

What Does a Commercial Insurance Agent in Winchester Cost?

Commercial insurance costs in Massachusetts vary widely based on business type, size, and risk level. A small retail shop might pay 500 to 1,500 dollars per year for general liability, while a construction firm could pay 5,000 to 15,000 dollars or more. Workers compensation rates are set by the state and depend on payroll and industry class codes. This is general information and not insurance advice.

* Cost estimates are general ranges based on publicly available data and compiled using automated research tools. Actual fees vary by agent and case complexity. This is not insurance advice — consult directly with an agent for fee specifics.

Frequently Asked Questions

What types of commercial insurance do businesses in Winchester need?
Common coverages include general liability, property insurance, and workers compensation. Massachusetts requires workers comp for nearly all employers with one or more employees. An agent can help assess your specific needs based on your industry and location.
How do Massachusetts laws affect commercial insurance requirements?
Massachusetts has strict liability laws and a high minimum auto liability limit of 20/40/5 for commercial vehicles. The state also requires employers to provide workers compensation insurance or face fines. A local agent understands these statutes and can help you stay compliant.