ADVERTISING DISCLOSURE: BeforeInsuranceUSA.com is an informational directory, not an insurance agency, broker, or licensed producer. We do not sell insurance or provide insurance advice. No agent-client relationship is created by using this site. Except where a listing is clearly marked Featured, no agent listed on this site has paid for their listing. Featured listings are paid advertisements. This is an advertisement.

Find Medicare Insurance Agents Near You in Westborough, MA

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

The top-rated medicare insurance agent in Westborough, Massachusetts is Dolan & Maloney Insurance Agency, LLC, rated 4.8 stars across 145 reviews. Other highly rated options include D&O Insurance Agency, Gaudette Insurance Agency, Amica Mutual Insurance Company. This directory lists 12 medicare insurance agents serving Westborough.

Showing 12 medicare insurance agents in Westborough, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Dolan & Maloney Insurance Agency, LLC141 Turnpike Rd(508) 366-4894
2D&O Insurance Agency125 Turnpike Rd Suite 6A(508) 859-6950
3Gaudette Insurance Agency86 E Main St(508) 366-8736
4Amica Mutual Insurance Company1 Research Dr #401b(888) 702-6422
5Abode Insurance Agency21 E Main St(508) 426-9872
6Secured Insurance Agency MA25 Brigham St(508) 850-0450
7Safety Northeast Insurance Agency, Inc.45 E Main St Suite 9(508) 898-2902
8Nikki Sidhu at Comparion Insurance Agency110 Turnpike Rd #201(508) 621-3671
9Smart Financial Lifestyle1500 W Park Dr Suite 100(800) 427-9781
10Health Plans, Inc. - Corporate Offices1500 W Park Dr #330(508) 752-2480
DM
141 Turnpike Rd
Dolan & Maloney Insurance Agency, LLC
Medicare Insurance Agent · Westborough, MA

Dolan & Maloney Insurance Agency, LLC serves the Worcester County and Metrowest region from Westborough, Massachusetts. It specializes in guiding local beneficiaries through their Medicare insurance options. The agency helps clients understand the differences between Original Medicare and Medicare Advantage plans. It also assists with the selection of standalone Part D prescription drug coverage. Specific services the agency handles in this area include enrolling clients in Medicare Supplement plans and navigating annual Medicare Advantage plan changes.

DI
125 Turnpike Rd Suite 6A
D&O Insurance Agency
Medicare Insurance Agent · Westborough, MA

D&O Insurance Agency provides personalized guidance through Medicare plan selections, including Advantage, Supplement, and Part D drug coverage. It assists clients in Westborough, MA with annual enrollment reviews and plan comparisons to align with changing healthcare needs. The agency helps navigate coverage options for current medical requirements and potential future changes. It also explains how plans coordinate with existing providers. D&O Insurance Agency serves single-family homes, apartments, retail, and restaurants.

GI
86 E Main St
Gaudette Insurance Agency
Medicare Insurance Agent · Westborough, MA

Gaudette Insurance Agency serves the residents of Westborough, Massachusetts, and the surrounding communities of central Worcester County. The agency handles Medicare insurance, including the options for Original Medicare Parts A and B, Medicare Advantage plans, and Medicare Part D prescription drug coverage. To serve its clients, it first reviews their current healthcare needs and budget to identify suitable plan choices. It then guides each individual through the enrollment process.

AM
1 Research Dr #401b
Amica Mutual Insurance Company
Medicare Insurance Agent · Westborough, MA

Serving homeowners and older adults in Westborough, Amica Mutual Insurance Company guides clients through Medicare insurance plan options, including supplement and Advantage policies. The agency helps individuals review coverage needs and enroll in suitable plans each enrollment period. By explaining the differences between plans, the agent assists clients in understanding their benefits and costs, ensuring informed decisions for their healthcare. The company also extends its Medicare insurance agent services to the neighboring communities of Northborough and Shrewsbury within the Worcester metro area.

AI
21 E Main St
Abode Insurance Agency
Medicare Insurance Agent · Westborough, MA

Abode Insurance Agency in Westborough, MA specializes in helping clients navigate Medicare Advantage, Medigap, and Part D prescription drug plans. As a local medicare insurance agent, it provides personalized guidance to seniors and those new to Medicare, clarifying complex coverage options. The agency assists individuals throughout the annual enrollment period and beyond. During the Medicare Open Enrollment season, it specifically helps policyholders reevaluate their existing plans to adjust for changes in health needs or prescription costs, ensuring comprehensive and suitable coverage.

SI
25 Brigham St
Secured Insurance Agency MA
Medicare Insurance Agent · Westborough, MA

As many seniors in the Westborough area begin reviewing their coverage options during the annual Medicare Open Enrollment period, Secured Insurance Agency MA helps clients navigate plan changes and new Part D prescription drug options. This local medicare insurance agent focuses on providing clear explanations of how Original Medicare differs from Medicare Advantage and Medigap supplemental plans. The agency emphasizes understanding each individual’s current health care needs and budget constraints. A typical initial step involves scheduling a free consultation to review existing coverage and assess potential adjustments.

SN
45 E Main St Suite 9
Safety Northeast Insurance Agency, Inc.
Medicare Insurance Agent · Westborough, MA

A Medicare Insurance Agent can help navigate the difference between an initial one-time enrollment and the ongoing need for reviewing annual plan changes. Safety Northeast Insurance Agency, Inc., located in Westborough, Massachusetts, assists clients with coverage options for Medicare, including supplements and prescription drug plans. Their service focuses on helping beneficiaries understand available choices in the local area. This agency provides guidance on a one-time, scheduled, or as-needed basis, depending on each client's enrollment or annual review needs.

NS
110 Turnpike Rd #201
Nikki Sidhu at Comparion Insurance Agency
Medicare Insurance Agent · Westborough, MA

Nikki Sidhu at Comparion Insurance Agency works with individuals in the Westborough, MA area to navigate Medicare coverage options. As a local Medicare insurance agent, the company helps clients understand the differences between Original Medicare and Medicare Advantage plans, as well as available prescription drug coverage. It also specializes in adding supplemental policies to fill gaps in standard benefits. The agency can serve those who manage offices, operate warehouses, or run food service businesses.

SF
1500 W Park Dr Suite 100
Smart Financial Lifestyle
Medicare Insurance Agent · Westborough, MA

Smart Financial Lifestyle provides Medicare insurance guidance to residents of Westborough, Massachusetts, helping them navigate plan options for their healthcare needs. The company assists with commercial coverage as well, serving local businesses and groups across the greater area. Their agents focus on explaining benefits and enrollment periods during appointments, ensuring clients understand their choices. Follow-up service is available before regular enrollment windows and whenever a client’s plan changes, allowing for ongoing support between visits.

HP
1500 W Park Dr #330
Health Plans, Inc. - Corporate Offices
Medicare Insurance Agent · Westborough, MA

Located in Westborough, MA, Health Plans, Inc. - Corporate Offices distinguishes between one-time plan comparisons and ongoing coverage management. This Medicare insurance agency helps local beneficiaries understand their options during initial enrollment and annual open enrollment periods. Their work often includes explaining plan benefits, navigating provider networks, and clarifying prescription drug coverage tiers. Appointment scheduling is available on a one-time, scheduled, or as-needed basis to accommodate varying client needs throughout the year.

NY
1700 W Park Dr #280
New York Life Insurance
Medicare Insurance Agent · Westborough, MA
(508) 616-4900
boston.nyloffices.com
SP
110 Turnpike Rd #201
Sophie Pearson
Medicare Insurance Agent · Westborough, MA
(508) 621-3673

What Does a a Medicare Insurance Agent in Westborough Cost?

Medicare insurance agents in Massachusetts do not charge you a fee for their services. They are compensated by insurance companies through commissions. The cost of Medicare plans varies: Part B premium is typically $174.70 per month in 2024, Medigap plans range from $100 to $300 per month depending on age and plan type, and Part D drug plans average $30 to $100 per month. This is general information, not insurance advice.

About medicare insurance agents in Westborough

Medicare insurance agents in Westborough, Massachusetts help residents navigate plan options during Initial Enrollment and the Annual Election Period. Massachusetts has a unique merged market for Medigap plans, which may affect your choices. An agent can explain how state rules like the Massachusetts Birthday Rule allow you to switch Medigap plans once per year without medical underwriting.

Frequently Asked Questions

What does a Medicare insurance agent in Westborough do?

A Medicare insurance agent helps you compare Part D drug plans, Medicare Advantage plans, and Medigap policies. They are licensed in Massachusetts and can explain how plans work with local providers like UMass Memorial Health or Boston hospitals.

When can I enroll in Medicare in Westborough?

Your Initial Enrollment Period starts three months before you turn 65 and ends three months after. Massachusetts also has a Special Enrollment Period for those who lose employer coverage. Missing deadlines may result in late penalties.

Are Medicare agents in Massachusetts free to use?

Most Medicare agents are paid by insurance carriers, not by you. Their services are typically offered at no direct cost to you. Always confirm the agent is appointed with the plans they recommend.

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.