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Find Health Insurance Agents in Winchester, MA

Browse health insurance agents serving Winchester, Massachusetts. Contact information and addresses listed below.

11 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 11 health 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
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
Black Horse Insurance
175 Washington St # C24, Winchester, MA 01890
(781) 729-1164 blackhorseinsurance.com
Ducey Insurance Agency
10 Skillings Rd, Winchester, MA 01890
(781) 235-6795

What Does a Health Insurance Agent in Winchester Cost?

Health insurance agents in Massachusetts do not charge you directly for their services. Their compensation comes from the insurance carrier. The cost of a health insurance plan varies widely based on age, income, and metal tier. A bronze plan for a 40-year-old in Winchester might cost around 450 to 600 dollars per month before subsidies. Subsidies from the Massachusetts Health Connector can lower that cost significantly. 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 does a health insurance agent in Winchester do?
A health insurance agent helps you review plan options from carriers like Blue Cross Blue Shield and Harvard Pilgrim. They explain deductibles, copays, and provider networks. They do not charge you a fee because they earn a commission from the insurance company.
When can I enroll in a health insurance plan in Massachusetts?
Open enrollment for individual plans typically runs from November 1 to January 23 each year. If you lose other coverage, move, or have a qualifying life event, you may qualify for a special enrollment period. You have 60 days from the event to enroll.
Do I need health insurance in Massachusetts?
Yes, Massachusetts has a health insurance mandate. If you go without qualifying coverage for more than three consecutive months, you may face a tax penalty. An agent can help you find a plan that meets the minimum creditable coverage standard.