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Compare Supplemental Insurance Agents in Winthrop, MA

Browse supplemental insurance agents serving Winthrop, Massachusetts. Contact information and addresses listed below.

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 supplemental 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

Supplemental insurance agents in Winthrop Massachusetts help residents fill gaps in Medicare and employer health plans. Massachusetts state law requires Medigap plans to be guaranteed issue for eligible beneficiaries during open enrollment. Local agents can explain plan options for Suffolk County residents.

What Does a Supplemental Insurance Agent in Winthrop Cost?

Medigap Plan G in Massachusetts typically costs between $120 and $250 per month for a 65 year old. Medicare Advantage plans often have $0 monthly premiums but may have copays and deductibles. Dental supplemental plans range from $25 to $60 per month. Actual costs depend on your age health and chosen plan. 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 is a supplemental insurance agent in Winthrop?
A supplemental insurance agent in Winthrop helps you buy policies that cover costs not paid by Medicare or primary health insurance. These agents are licensed in Massachusetts and can explain Medigap Medicare Advantage and dental plans.
When can I enroll in a Medigap plan in Massachusetts?
Massachusetts has a six-month Medigap open enrollment period starting when you are 65 and enrolled in Medicare Part B. During this time insurers cannot deny coverage or charge higher premiums for pre-existing conditions.
Do Massachusetts agents charge fees for supplemental insurance?
Most supplemental insurance agents in Massachusetts are paid commissions by the insurance company not by you. You should ask the agent if any fees apply before you sign up.