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Directory of medicare insurance agents in Pittsfield, Massachusetts. Verify credentials with the state department of insurance before hiring.
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 medicare 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
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
Taillefer Insurance
446 South St, Pittsfield, MA 01201
(413) 445-5616
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
Aflac Insurance: Joseph Hervieux
961 Dalton Ave, Pittsfield, MA 01201
(413) 214-2059
New York Life
7 North St Suite LL1, Pittsfield, MA 01201
(413) 442-8067
newyorklife.com
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
Arsenault Insurance Adjusters
172 First St, Pittsfield, MA 01201
(413) 499-2121
Medicare insurance agents in Pittsfield, Massachusetts help residents navigate Original Medicare, Medicare Advantage, and Part D drug plans. Massachusetts has a unique annual enrollment period from October 15 to December 7, and agents can assist with plan comparisons and enrollment. Local agents understand the Berkshire County healthcare network and can guide you through options that fit your needs and budget.
What Does a Medicare Insurance Agent in Pittsfield Cost?
Medicare insurance agents in Massachusetts generally do not charge you directly for their services. They receive commissions from insurance carriers when you enroll in a plan. Some agents may offer additional consulting for a flat fee, which can range from 50 to 200 dollars per session. Costs vary by situation, plan type, and the agent's business model. 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 Medicare insurance agent in Pittsfield do?
A Medicare insurance agent helps you compare and enroll in Medicare plans, including Advantage and Part D plans. They explain coverage details, costs, and network restrictions for plans available in Berkshire County. Agents are licensed in Massachusetts and can assist with annual enrollment and special enrollment periods.
Do I have to pay for a Medicare insurance agent in Massachusetts?
In most cases, Medicare insurance agents are paid by the insurance companies, not by you. Their services are typically free to the consumer. However, some agents may charge a fee for certain advisory services, so always ask about costs upfront.
When can I enroll in a Medicare plan in Pittsfield?
The Initial Enrollment Period starts three months before your 65th birthday and ends three months after. Massachusetts also follows the federal Annual Enrollment Period from October 15 to December 7. You may qualify for a Special Enrollment Period if you move, lose other coverage, or meet other criteria.
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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.