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Compare Medicare Insurance Agents in Winthrop, MA

Looking for a medicare insurance agent in Winthrop? Review the directory below to compare your options.

10 agents listed
Updated May 2026
Winthrop, 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 10 medicare insurance agents in Winthrop, 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.
John M. Biggio Ins Agency
399 Winthrop St, Winthrop, MA 02152
(617) 846-8600 biggioinsurance.com
Robert M DeGregorio Insurance
34 Woodside Ave, Winthrop, MA 02152
(617) 846-3313 rmdins.com
Winthrop Insurance Inc.
4 Putnam St, Winthrop, MA 02152
(339) 204-6737
OneFuture Insurance MA
15-21 Pauline St, Winthrop, MA 02152
(617) 433-9205
Gagin Insurance Agency
2 Somerset Ave, Winthrop, MA 02152
(617) 846-0091
Welsh & Parker Insurance Agency
57 Putnam St, Winthrop, MA 02152
(617) 846-0731 baldwinweb.com
Boyd Insurance Agency
207 Hagman Rd, Winthrop, MA 02152
(617) 846-9728
Meridian Insurance Agency, LLC
207 Hagman Rd, Winthrop, MA 02152
(617) 567-5710
Terry Vazquez Public Insurance
49 Adams St, Winthrop, MA 02152
(617) 846-6309
New York Life
207 Hagman Rd, Winthrop, MA 02152
(617) 846-0630 newyorklife.com

Medicare insurance agents in Winthrop, Massachusetts help residents navigate Original Medicare, Medicare Advantage, and Part D prescription drug plans. Massachusetts state law requires agents to be licensed and to follow strict guidelines during the Annual Enrollment Period from October 15 to December 7. Local agents understand the specific needs of Winthrop seniors, including access to nearby hospitals and specialists.

What Does a Medicare Insurance Agent in Winthrop Cost?

Medicare insurance agents in Massachusetts are typically paid by insurance companies through commissions, so their services are usually free to you. However, plan costs vary by carrier and coverage level. For example, Medicare Advantage plans may have $0 premiums or premiums up to $200 per month, while Medigap plans can range from $100 to $400 per month depending on your age and health. 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 does a Medicare insurance agent in Winthrop do?
A Medicare insurance agent helps you compare plans, understand coverage options, and enroll in Medicare Part A, Part B, Medicare Advantage, or Part D. They are licensed in Massachusetts and can explain how plans work with local providers.
When can I enroll in Medicare in Massachusetts?
Your Initial Enrollment Period starts three months before your 65th birthday and ends three months after. Massachusetts also has a General Enrollment Period from January 1 to March 31 each year for those who missed initial sign up.