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Directory of truck insurance agents in Winchester, Massachusetts. Verify credentials with the state department of insurance before hiring.
13 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 13 truck 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
Northeast Adjustment Bureau
24 River St, Winchester, MA 01890
(781) 721-3300
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
Truck insurance agents in Winchester Massachusetts help owner-operators and fleet managers secure the right commercial auto coverage. Massachusetts requires all commercial trucks to carry liability insurance with minimum limits of 750000 dollars for bodily injury per accident. Local agents understand the specific filing requirements of the Massachusetts Division of Insurance and can guide you through the process.
What Does a Truck Insurance Agent in Winchester Cost?
Typical annual premiums for truck insurance in Massachusetts range from 8000 to 15000 dollars for a single owner-operator with a clean record. Fleet policies can cost 25000 dollars or more depending on vehicle count and cargo type. Factors like driving history vehicle value and coverage limits affect the final price. This is general information 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 truck insurance do agents in Winchester offer?
Agents typically offer liability coverage physical damage coverage cargo insurance and non-trucking liability. They also provide coverage for hired and non-owned trucks as needed for Massachusetts-based operations.
Do I need a specific license to drive a commercial truck in Massachusetts?
Yes Massachusetts requires a Commercial Drivers License (CDL) for vehicles over 26000 pounds gross vehicle weight rating or those carrying hazardous materials. Your insurance agent can help ensure your policy matches your CDL class.
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BeforeInsuranceUSA.com is not an insurance agency, agent referral service, or insurance advice provider. No agent-client relationship is formed by submitting a form or using this site. We do not endorse, recommend, or vouch for the qualifications of any agent. Past results do not guarantee future outcomes. Each situation is different. Verify agent credentials with your state department of insurance before hiring.
About Our Listings
Agents listed on BeforeInsuranceUSA.com are compiled from publicly available directories, state department of insurance records, and business listings. Inclusion does not constitute endorsement. We do not verify agent licensing, disciplinary status, or qualifications. Verify each agent's current standing with the Department of Insurance of Massachusetts.