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Find Health Insurance Agents Near You in Pittsfield, MA

Compare health insurance agents in Pittsfield. Review contact information and insurance categorys before you decide.

19 agents listed
Updated May 2026
Pittsfield, 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 19 health insurance agents in Pittsfield, 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.
AAA Pittsfield
660 Merrill Rd, Pittsfield, MA 01201
(413) 445-5635 branches.northeast.aaa.com
Pearson Wallace Insurance, LLC
222 South St, Pittsfield, MA 01201
(413) 464-9390 pearsonwallace.com
Greylock Insurance Agency
5 Cheshire Rd Suite 26, Pittsfield, MA 01201
(413) 443-5943 greylockinsurance.com
MOLARI Employment and HealthCare Services
166 East St, Pittsfield, MA 01201
(413) 499-4546 molariinc.com
Home Instead
66 Wendell Ave, Pittsfield, MA 01201
(413) 910-9131 homeinstead.com
MountainOne Insurance
111 Silver Lake Blvd, Pittsfield, MA 01201
(413) 442-9241 mountainone.com
Shire City Insurance
446 South St #1, Pittsfield, MA 01201
(413) 443-9359
Wheeler & Taylor Insurance
402 East St, Pittsfield, MA 01201
(413) 448-8224 wheelertaylor.com
Berkshire Insurance Group
43 East St, Pittsfield, MA 01201
(866) 636-0244 berkshirebank.com
National Financial Network
700 South St, Pittsfield, MA 01201
(800) 819-2468 agencies.guardianlife.com
Greylock Insurance Agency
150 West St, Pittsfield, MA 01201
(413) 236-4840 greylockinsurance.com
MountainOne Insurance
101 South St, Pittsfield, MA 01201
(413) 445-5648 mountainone.com
Berkshire Fairfield Insurance Agency, LLC
128 South St, Pittsfield, MA 01201
(413) 443-0077 berkshirefairfieldinsurance.com
Scarafoni Financial Group LLC
128 South St, Pittsfield, MA 01201
(413) 443-5300 scarafonifinancial.com
Northwestern Mutual
55 North St #304, Pittsfield, MA 01201
(413) 499-0620 northwesternmutual.com
Taillefer Insurance
446 South St, Pittsfield, MA 01201
(413) 445-5616
Health Options
648 North St, Pittsfield, MA 01201
(413) 464-9400
Health New England-Berkshire
75 S Church St, Pittsfield, MA 01201
(413) 499-8887
Berkshire Insurance Group Inc
Allendale Shopping Center, 39 Cheshire Rd, Pittsfield, MA 01201
(413) 447-3510

Health insurance agents in Pittsfield, Massachusetts help individuals and families find coverage through the Massachusetts Health Connector, the state-based marketplace. These agents are licensed by the Massachusetts Division of Insurance and can assist with plans that comply with the state individual mandate requiring residents to maintain health insurance. Local agents understand the specific needs of Berkshire County residents and can guide you through enrollment periods and subsidy eligibility.

What Does a Health Insurance Agent in Pittsfield Cost?

Health insurance agents in Massachusetts are typically paid by insurance carriers through commissions, so their services are usually free to you. Premiums for individual plans through the Health Connector vary widely based on income, age, and plan tier, with monthly costs ranging from under 100 dollars for subsidized plans to over 500 dollars for unsubsidized gold or platinum plans. Medicare supplement plans in Pittsfield generally cost between 100 and 300 dollars per month depending on the carrier and plan type. 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 is the open enrollment period for health insurance in Massachusetts?
The Massachusetts Health Connector open enrollment typically runs from November 1 to January 23 each year. Outside this period, you may qualify for a special enrollment period if you experience a qualifying life event such as losing job-based coverage, moving, or having a baby.
Do I need health insurance in Massachusetts?
Yes, Massachusetts has an individual mandate that requires most residents to have health insurance that meets minimum creditable coverage standards. If you do not have coverage, you may face a tax penalty when filing your state taxes.
Can a health insurance agent help me with MassHealth?
Yes, many health insurance agents in Pittsfield are certified to help you apply for MassHealth, Massachusetts Medicaid program. They can determine your eligibility and guide you through the application process.