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Find Medicare Insurance Agents Near You in Pittsfield, MA

Browse medicare insurance agents serving Pittsfield, Massachusetts. Updated 2026-07-14.

The top-rated medicare insurance agent in Pittsfield, Massachusetts is Pearson Wallace Insurance, LLC, rated 4.9 stars across 113 reviews. Other highly rated options include AAA Pittsfield, Greylock Insurance Agency, MountainOne Insurance. This directory lists 20 medicare insurance agents serving Pittsfield.

Showing 20 medicare insurance agents in Pittsfield, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Pearson Wallace Insurance, LLC222 South St(413) 464-9390
2AAA Pittsfield660 Merrill Rd(413) 445-5635
3Greylock Insurance Agency5 Cheshire Rd Suite 26(413) 443-5943
4MountainOne Insurance111 Silver Lake Blvd(413) 442-9241
5Shire City Insurance446 South St #1(413) 443-9359
6Wheeler & Taylor Insurance402 East St(413) 448-8224
7Berkshire Insurance Group43 East St(866) 636-0244
8National Financial Network700 South St(800) 819-2468
9Taillefer Insurance446 South St(413) 445-5616
10Berkshire Fairfield Insurance Agency, LLC128 South St(413) 443-0077
PW
222 South St
Pearson Wallace Insurance, LLC
Medicare Insurance Agent · Pittsfield, MA

Pearson Wallace Insurance, LLC provides Medicare insurance guidance, including plan comparisons and enrollment assistance, to clients in Pittsfield, MA. It helps individuals navigate the annual enrollment period and explains coverage options such as Medicare Advantage and Supplement plans. Ongoing support is available for plan changes, claims questions, and prescription drug coverage needs. The agency also offers annual plan reviews to ensure coverage keeps pace with health requirements. Its services reach single-family homes, apartments, retail, and restaurants.

AP
660 Merrill Rd
AAA Pittsfield
Medicare Insurance Agent · Pittsfield, MA

AAA Pittsfield serves the Berkshire County area of Massachusetts, offering professional Medicare insurance guidance. As a local agency, it helps individuals navigate the complexities of Medicare plans, including enrollment periods and policy comparisons. The company focuses on explaining coverage options clearly, ensuring clients understand their benefits. Services typically include finding suitable Part D prescription drug plans and helping seniors transition smoothly from employer coverage. By working directly with clients, they assist with plan selection for both Medicare Supplement and Medicare Advantage options in the Pittsfield region.

GI
5 Cheshire Rd Suite 26
Greylock Insurance Agency
Medicare Insurance Agent · Pittsfield, MA

Serving residential clients in Pittsfield, Greylock Insurance Agency offers guidance on Medicare insurance coverage. Commercial coverage is also available, and the agency serves Berkshire County and the surrounding areas. Enrollment periods are explained clearly, helping individuals understand their plan choices and potential cost implications. The agent follows up with clients after their initial enrollment and provides continued support between annual open enrollment periods to address changes in healthcare needs.

MI
111 Silver Lake Blvd
MountainOne Insurance
Medicare Insurance Agent · Pittsfield, MA

MountainOne Insurance in Pittsfield, Massachusetts, is known for guiding clients through Medicare plan options. Its service range includes helping individuals evaluate Medicare Supplement and Medicare Advantage plans available in the county. The company assists with enrollment periods and plan comparisons. With a focus on personal consultations, it clarifies how different policies cover medical costs for residents in the Berkshires. This Medicare insurance agent offers specialized support for navigating the annual open enrollment changes in local carrier networks.

SC
446 South St #1
Shire City Insurance
Medicare Insurance Agent · Pittsfield, MA

For Medicare insurance needs, Shire City Insurance in Pittsfield, MA helps individuals first distinguish between one-time plan enrollment assistance and ongoing coverage management. They address both initial plan selection during eligibility and later options, including reviewing annual changes or adjusting supplemental or prescription drug coverage as needed. Ongoing support ensures policies keep pace with health and budget shifts throughout the year. Their service runs on either a one-time appointment or an as-needed, scheduled basis when clients require help or a review.

WT
402 East St
Wheeler & Taylor Insurance
Medicare Insurance Agent · Pittsfield, MA

Wheeler & Taylor Insurance specializes in Medicare insurance agent services for Pittsfield, Massachusetts, and the surrounding area. It enrolls clients in Medicare Advantage, Part D prescription drug plans, and Medigap supplemental policies. The agency reviews each individual’s health needs and budget to find suitable coverage. It helps with plan comparisons and explains the annual enrollment period options. During tax season, it also assists clients in understanding how Medicare premiums affect their adjusted gross income calculations.

BI
43 East St
Berkshire Insurance Group
Medicare Insurance Agent · Pittsfield, MA

As the annual Medicare enrollment period approaches, residents of Pittsfield, Massachusetts often seek clarity on new plan options and coverage changes. Berkshire Insurance Group provides localized guidance on Part D drug plans, Medicare Advantage, and supplemental policies for the surrounding area. Their services are designed to help seniors assess their current health needs and compare available choices. An initial consultation typically includes a review of the beneficiary’s existing coverage and a thorough needs assessment to identify the most suitable plan for inspection.

NF
700 South St
National Financial Network
Medicare Insurance Agent · Pittsfield, MA

National Financial Network, located in Pittsfield, Massachusetts, provides guidance on Medicare insurance options, helping clients navigate plan selections during enrollment periods. The company specializes in supplementing original Medicare with coverage for prescription drugs, vision, dental, and hearing services. It also addresses plan changes for those turning sixty-five or retiring. Within the local area, the firm works with commercial operations such as offices, warehouses, and food service establishments to arrange group or individual Medicare solutions for their employees or themselves.

TI
446 South St
Taillefer Insurance
Medicare Insurance Agent · Pittsfield, MA

Taillefer Insurance provides personalized Medicare health plan guidance to individuals across Pittsfield, Massachusetts. It assists clients with plan selection during enrollment periods. The company also offers ongoing policy review and annual benefit updates. This ensures coverage adapts to changing healthcare needs and prescription drug requirements. Taillefer Insurance serves a diverse range of local residences, including single-family homes and apartment dwellers, as well as small retail businesses and neighborhood restaurants in the Pittsfield area.

BF
128 South St
Berkshire Fairfield Insurance Agency, LLC
Medicare Insurance Agent · Pittsfield, MA

Berkshire Fairfield Insurance Agency, LLC serves seniors and individuals approaching Medicare eligibility in Pittsfield, Massachusetts. Its Medicare Insurance Agents help clients compare plan options, enroll in coverage, and understand annual changes to benefits. The agency supports those seeking to navigate Original Medicare, Advantage plans, and prescription drug coverage with personalized guidance. Each appointment focuses on identifying the most suitable policy for specific health needs and budgets. It also extends its services to clients in the neighboring community of Lenox and throughout central Berkshire County.

GI
150 West St
Greylock Insurance Agency
Medicare Insurance Agent · Pittsfield, MA
(413) 236-4840
greylockinsurance.com
MI
101 South St
MountainOne Insurance
Medicare Insurance Agent · Pittsfield, MA
(413) 445-5648
mountainone.com/insurance
SF
128 South St
Scarafoni Financial Group LLC
Medicare Insurance Agent · Pittsfield, MA
(413) 443-5300
scarafonifinancial.com
AI
961 Dalton Ave
Aflac Insurance: Joseph Hervieux
Medicare Insurance Agent · Pittsfield, MA
(413) 214-2059
NY
7 North St Suite LL1
New York Life
Medicare Insurance Agent · Pittsfield, MA
(413) 442-8067
newyorklife.com
HO
648 North St
Health Options
Medicare Insurance Agent · Pittsfield, MA
(413) 464-9400
BI
75 South Church Street Pittsfield Lenox
Berkshire Insurance Group
Medicare Insurance Agent · Pittsfield, MA
(866) 636-0244
HN
75 S Church St
Health New England-Berkshire
Medicare Insurance Agent · Pittsfield, MA
(413) 499-8887
BI
Allendale Shopping Center, 39 Cheshire Rd
Berkshire Insurance Group Inc
Medicare Insurance Agent · Pittsfield, MA
(413) 447-3510
AI
172 First St
Arsenault Insurance Adjusters
Medicare Insurance Agent · Pittsfield, MA
(413) 499-2121

What Does a 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 case, plan type, and the agent's business model. This is general information, not insurance advice.

About medicare insurance agents in Pittsfield

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.

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.

Medicare Insurance Agents in Other Massachusetts Cities

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each medicare insurance agent's credentials and current standing with your state Department of Insurance.