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Directory of supplemental insurance agents in Pittsfield, Massachusetts. Verify credentials with the state department of insurance before hiring.
20 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 20 supplemental 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
Berkshire Fairfield Insurance Agency, LLC
128 South St, Pittsfield, MA 01201
(413) 443-0077
berkshirefairfieldinsurance.com
Taillefer Insurance
446 South St, Pittsfield, MA 01201
(413) 445-5616
Scarafoni Financial Group LLC
128 South St, Pittsfield, MA 01201
(413) 443-5300
scarafonifinancial.com
Mclaughlin John
55 North St #304, Pittsfield, MA 01201
(413) 499-0620
johnfmclaughliniii.nm.com
Northwestern Mutual
55 North St #304, Pittsfield, MA 01201
(413) 499-0620
northwesternmutual.com
Aflac Insurance: Joseph Hervieux
961 Dalton Ave, Pittsfield, MA 01201
(413) 214-2059
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
Suzanne Eisermann - Aflac Insurance Agent
359 Pecks Rd, Pittsfield, MA 01201
(413) 442-0350
New York Life
7 North St Suite LL1, Pittsfield, MA 01201
(413) 442-8067
newyorklife.com
Supplemental insurance agents in Pittsfield, Massachusetts help residents fill gaps in Medicare coverage, such as copayments and deductibles. Massachusetts law requires Medigap plans to be guaranteed issue during the six-month open enrollment period starting when you turn 65. Local agents can explain how Massachusetts standardized Medigap plans A through N work for Berkshire County seniors.
What Does a Supplemental Insurance Agent in Pittsfield Cost?
Supplemental insurance costs in Massachusetts vary by plan type, age, and insurer. Monthly premiums for Medigap Plan G in Pittsfield typically range from $120 to $250 for a 65-year-old. Plan N may cost $90 to $180 per month. Rates can increase each year due to inflation and claims experience. 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 is a supplemental insurance agent in Pittsfield?
A supplemental insurance agent in Pittsfield helps you buy Medigap or Medicare Supplement plans. These agents are licensed in Massachusetts and can compare plans from multiple carriers. They do not sell Medicare Advantage plans unless they also hold that certification.
When can I enroll in a Medigap plan in Massachusetts?
In Massachusetts, you have a six-month open enrollment period starting the month you turn 65 and enroll in Medicare Part B. During this time, insurers cannot deny you coverage or charge higher premiums due to health conditions. Outside this window, you may face medical underwriting.
Are Medigap plans standardized in Massachusetts?
Yes, Massachusetts standardizes Medigap plans into types A through N. Each plan type offers the same benefits regardless of which insurance company sells it. This makes it easier to compare prices and coverage options with a local agent.
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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.