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Find Supplemental Insurance Agents Near You in Pittsfield, MA

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

The top-rated supplemental 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 supplemental insurance agents serving Pittsfield.

Showing 20 supplemental 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
9Berkshire Fairfield Insurance Agency, LLC128 South St(413) 443-0077
10Taillefer Insurance446 South St(413) 445-5616
PW
222 South St
Pearson Wallace Insurance, LLC
Supplemental Insurance Agent · Pittsfield, MA

Pearson Wallace Insurance, LLC offers a range of supplemental insurance policies designed to fill gaps in primary health coverage for clients in Pittsfield, MA. The agency assists individuals and families in selecting plans that help manage out-of-pocket expenses not covered by standard medical insurance. Service includes consulting with clients to review existing coverage, identifying potential coverage gaps, and explaining plan options in a clear manner. Regular policy reviews ensure plans remain appropriate as client needs change. Pearson Wallace Insurance serves single-family homes, apartments, retail operations, and restaurants.

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

AAA Pittsfield serves the Pittsfield, Massachusetts area, specializing in supplemental insurance coverage. The agency helps local residents secure policies that fill gaps left by major medical plans. These supplemental plans are designed to cover out-of-pocket expenses like deductibles and copayments. The company brokers various insurance options for individuals seeking financial protection against unexpected healthcare costs. It handles specific needs such as hospital indemnity plans and critical illness insurance.

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

Greylock Insurance Agency provides supplemental insurance solutions to residents of Pittsfield, Massachusetts, offering coverage that fills gaps left by major medical plans. The agency also serves local commercial clients needing supplemental protection for their businesses. Service extends throughout the Berkshires region. Policies focus on predictable benefits for unexpected health or accident costs, helping clients manage out-of-pocket expenses. Agents schedule annual policy reviews to adjust coverage as needs change and provide ongoing follow-up assistance between regular visits.

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

MountainOne Insurance is a supplemental insurance agent serving Pittsfield, MA, known for helping clients fill coverage gaps left by standard health plans. Its service range spans accident, critical illness, hospital indemnity, and disability income policies. Licensed professionals in this area work to identify individual needs for added financial protection. A specialty service the agency can provide is final expense insurance for funeral and end-of-life planning.

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

Shire City Insurance serves Pittsfield residents by differentiating between one-time supplemental coverage options, which protect against a single unforeseen medical expense, and recurring policies that provide ongoing financial support for repeated health care needs. Their coverage helps fill gaps left by major medical plans, ensuring individuals face fewer out-of-pocket costs for deductibles or co-payments. Service appointments are available on an as-needed basis, allowing clients to request consultations, policy adjustments, or claims assistance only when a specific concern arises.

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

Wheeler & Taylor Insurance specializes in providing supplemental insurance agent services in Pittsfield, MA, helping clients fill gaps left by primary health plans. It offers guidance on policies that cover out-of-pocket medical expenses, critical illness events, or accident-related costs. The agency works with individuals and families to assess personal needs and select appropriate coverage. As winter approaches, it assists residents in evaluating supplemental plans that address increased seasonal risks like flu complications or holiday travel emergencies.

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

As Pittsfield residents prepare for the winter months, gaps in standard health plans often become apparent. Berkshire Insurance Group specializes in supplemental insurance solutions tailored to these coverage shortfalls. Serving the community, they assist individuals in understanding Medicare supplements and other policies designed to address out-of-pocket costs. Their process begins with a thorough review of each client’s current coverage before recommending any additional options. A licensed agent then conducts an initial needs assessment to identify specific gaps and discuss available choices for more comprehensive protection.

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

National Financial Network works in Pittsfield, Massachusetts, as a supplemental insurance agent, helping individuals cover gaps that major medical plans often leave behind. The company focuses on policies that address specific out-of-pocket expenses, such as accident or critical illness costs. By specializing in these add-ons, the agency can assist both workers and business owners in protecting against financial strain. Its insurance solutions can be utilized across many commercial environments, including offices, warehouses, and food service operations.

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

Berkshire Fairfield Insurance Agency, LLC provides supplemental insurance coverage to individuals in Pittsfield, Massachusetts. Its specialty add-ons help fill gaps left by primary policies, offering financial support for unexpected medical costs and lost income. These policies can be tailored to address specific needs without requiring extensive underwriting. The agency works with a variety of commercial sectors it can serve, including offices, warehouses, and food service operations.

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

Taillefer Insurance serves residential clients in Pittsfield, Massachusetts by providing supplemental insurance coverage for gaps in primary health plans. The company also offers commercial supplemental policies tailored to local businesses throughout the Berkshire County area. Agents work directly with individuals to explain policy options and facilitate enrollment. After an initial plan is established, the agency maintains contact with clients to adjust coverage as needs change, scheduling follow-up appointments between regular service visits.

GI
150 West St
Greylock Insurance Agency
Supplemental Insurance Agent · Pittsfield, MA
(413) 236-4840
greylockinsurance.com
MI
101 South St
MountainOne Insurance
Supplemental Insurance Agent · Pittsfield, MA
(413) 445-5648
mountainone.com/insurance
SF
128 South St
Scarafoni Financial Group LLC
Supplemental Insurance Agent · Pittsfield, MA
(413) 443-5300
scarafonifinancial.com
MJ
55 North St #304
Mclaughlin John
Supplemental Insurance Agent · Pittsfield, MA
(413) 499-0620
johnfmclaughliniii.nm.com
NM
55 North St #304
Northwestern Mutual
Supplemental Insurance Agent · Pittsfield, MA
(413) 499-0620
northwesternmutual.com/financial-professionals
AI
961 Dalton Ave
Aflac Insurance: Joseph Hervieux
Supplemental Insurance Agent · Pittsfield, MA
(413) 214-2059
HO
648 North St
Health Options
Supplemental Insurance Agent · Pittsfield, MA
(413) 464-9400
HN
75 S Church St
Health New England-Berkshire
Supplemental Insurance Agent · Pittsfield, MA
(413) 499-8887
SE
359 Pecks Rd
Suzanne Eisermann - Aflac Insurance Agent
Supplemental Insurance Agent · Pittsfield, MA
(413) 442-0350
NY
7 North St Suite LL1
New York Life
Supplemental Insurance Agent · Pittsfield, MA
(413) 442-8067
newyorklife.com

What Does a 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.

About supplemental insurance agents in Pittsfield

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.

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.

Supplemental Insurance Agents in Other Massachusetts Cities

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