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Find Health Insurance Agents Near You in Pittsfield, MA

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

The top-rated health 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, Home Instead. This directory lists 20 health insurance agents serving Pittsfield.

Showing 20 health 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
4Home Instead66 Wendell Ave(413) 910-9131
5MOLARI Employment and HealthCare Services166 East St(413) 499-4546
6MountainOne Insurance111 Silver Lake Blvd(413) 442-9241
7Shire City Insurance446 South St #1(413) 443-9359
8Wheeler & Taylor Insurance402 East St(413) 448-8224
9Berkshire Insurance Group43 East St(866) 636-0244
10National Financial Network700 South St(800) 819-2468
PW
222 South St
Pearson Wallace Insurance, LLC
Health Insurance Agent · Pittsfield, MA

Pearson Wallace Insurance, LLC provides health insurance agent services in Pittsfield, MA, assisting clients with individual and family plans, Medicare options, and group coverage. It also offers long-term support for policy renewals, claims assistance, and annual plan reviews to ensure coverage remains appropriate. The company serves a variety of property owners, including single-family homes, apartments, retail spaces, and restaurants.

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

AAA Pittsfield serves the Pittsfield, Massachusetts metro area as a local health insurance agent. It connects individuals and families with suitable medical coverage plans. The company assists clients in understanding their policy options and navigating enrollment periods. It works with major insurance carriers to offer a range of health plans. Services include helping customers compare benefits and coverage details during open enrollment. AAA Pittsfield specifically handles plan selections for both individual health policies and family coverage options.

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

Greylock Insurance Agency serves homeowners, individuals, and small business owners in Pittsfield, Massachusetts, by helping them navigate the local health insurance market. It assists clients in comparing individual and family plans, providing clear explanations of policy options and coverage details. The agency works to match each customer with a suitable health plan based on their specific needs and budget. Its service area also extends to the neighboring communities of Lenox and the greater Berkshire County region.

HI
66 Wendell Ave
Home Instead
Health Insurance Agent · Pittsfield, MA

Home Instead in Pittsfield, MA helps clients distinguish between the one-time enrollment assistance for a new plan and the ongoing service of adjusting coverage as annual policies or personal health needs change. As a health insurance agent, the company guides individuals and families through the selection of medical, dental, or supplemental plans that fit their specific budget. This service operates on either a scheduled appointment basis or as needed when a client requests a plan review.

ME
166 East St
MOLARI Employment and HealthCare Services
Health Insurance Agent · Pittsfield, MA

Serving Pittsfield, Massachusetts, and the surrounding Berkshire County communities, MOLARI Employment and HealthCare Services handles a range of health insurance needs for individuals and local businesses. It navigates plan options, helping clients evaluate coverage for medical, prescription, and preventive care. The company also addresses eligibility questions and enrollment processes. For a typical job, it first reviews the client’s current coverage and budget, then compares available plans to recommend a suitable option that meets their specific care needs.

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

MountainOne Insurance provides health insurance agent services in Pittsfield, MA, specializing in helping individuals and families enroll in qualified health plans through the Massachusetts Health Connector. It also assists local small businesses in finding suitable group coverage options that comply with state regulations. Navigating annual open enrollment periods can be confusing, so the agency helps clients understand their changing plan choices and potential subsidies before the deadlines expire.

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

As the Berkshire winters often bring a heightened focus on well-being, Shire City Insurance of Pittsfield, MA provides health insurance agent services to address local coverage needs. The company guides individuals through plan options during open enrollment and qualifying life events, helping clients navigate the complexities of medical, dental, and supplemental policies common to this market. Their work involves explaining how regional networks and prescription drug tiers match customer health needs across the county. An in-person office consultation is the standard starting point for an initial coverage review.

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

Wheeler & Taylor Insurance operates as a licensed health insurance agency providing coverage solutions to individuals and groups in the greater Pittsfield area. As a specialized health insurance agent, the firm focuses on helping clients navigate plan selection, enrollment, and annual renewals for medical and supplemental policies. Through its advisory process, the agency evaluates existing coverage to identify potential gaps and adjust for changing healthcare needs or budget considerations. This local agency serves a wide range of commercial sectors, including offices, warehouses, and food service businesses.

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

Serving residential clients in Pittsfield, Berkshire Insurance Group facilitates health insurance coverage for individuals and families. Commercial health plans are also arranged for local businesses in the surrounding area. A licensed agent works to explain plan options and assist with enrollment. Guidance is offered for annual renewals and policy changes when life circumstances shift. Follow-up communication is maintained between regular appointments to address any emerging coverage questions or claims issues.

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

National Financial Network in Pittsfield, MA is known for helping individuals and families navigate health insurance options. The agency provides guidance on selecting plans that match varied needs and budgets, including marketplace and private policies. Clients receive straightforward explanations of coverage terms and potential out-of-pocket costs. The team focuses on annual enrollment assistance and plan comparisons. An additional specialty service includes aiding clients with Medicare supplement plan selections to fill gaps in original Medicare coverage.

GI
150 West St
Greylock Insurance Agency
Health Insurance Agent · Pittsfield, MA
(413) 236-4840
greylockinsurance.com
MI
101 South St
MountainOne Insurance
Health Insurance Agent · Pittsfield, MA
(413) 445-5648
mountainone.com/insurance
BF
128 South St
Berkshire Fairfield Insurance Agency, LLC
Health Insurance Agent · Pittsfield, MA
(413) 443-0077
berkshirefairfieldinsurance.com
SF
128 South St
Scarafoni Financial Group LLC
Health Insurance Agent · Pittsfield, MA
(413) 443-5300
scarafonifinancial.com
NM
55 North St #304
Northwestern Mutual
Health Insurance Agent · Pittsfield, MA
(413) 499-0620
northwesternmutual.com/financial-professionals
TI
446 South St
Taillefer Insurance
Health Insurance Agent · Pittsfield, MA
(413) 445-5616
HO
648 North St
Health Options
Health Insurance Agent · Pittsfield, MA
(413) 464-9400
HN
75 S Church St
Health New England-Berkshire
Health Insurance Agent · Pittsfield, MA
(413) 499-8887
BI
Allendale Shopping Center, 39 Cheshire Rd
Berkshire Insurance Group Inc
Health Insurance Agent · Pittsfield, MA
(413) 447-3510
BI
75 South Church Street Pittsfield Lenox
Berkshire Insurance Group
Health Insurance Agent · Pittsfield, MA
(866) 636-0244

What Does a 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.

About health insurance agents in Pittsfield

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.

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.

Health Insurance Agents in Other Massachusetts Cities

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