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Find Medicare Insurance Agents Near You in Winthrop, MA

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

The top-rated medicare insurance agent in Winthrop, Massachusetts is John M. Biggio Ins Agency, rated 4.7 stars across 36 reviews. Other highly rated options include Robert M DeGregorio Insurance, Winthrop Insurance Inc., OneFuture Insurance MA. This directory lists 10 medicare insurance agents serving Winthrop.

Showing 10 medicare insurance agents in Winthrop, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1John M. Biggio Ins Agency399 Winthrop St(617) 846-8600
2Robert M DeGregorio Insurance34 Woodside Ave(617) 846-3313
3Winthrop Insurance Inc.4 Putnam St(339) 204-6737
4OneFuture Insurance MA15-21 Pauline St(617) 433-9205
5Gagin Insurance Agency2 Somerset Ave(617) 846-0091
6Welsh & Parker Insurance Agency57 Putnam St(617) 846-0731
7Boyd Insurance Agency207 Hagman Rd(617) 846-9728
8Meridian Insurance Agency, LLC207 Hagman Rd(617) 567-5710
9Terry Vazquez Public Insurance49 Adams St(617) 846-6309
10New York Life207 Hagman Rd(617) 846-0630
JM
399 Winthrop St
John M. Biggio Ins Agency
Medicare Insurance Agent · Winthrop, MA

John M. Biggio Ins Agency serves the Winthrop, Massachusetts area as a local Medicare insurance agent. The company helps clients navigate Medicare options, including plan selection and enrollment guidance. It assists with understanding Original Medicare, Medicare Advantage, and Medicare Part D prescription drug plans. The agent works to match individuals with coverage that fits their needs. Specific services include annual plan review and assisting with Medicare Supplement insurance for supplemental coverage.

RM
34 Woodside Ave
Robert M DeGregorio Insurance
Medicare Insurance Agent · Winthrop, MA

Robert M DeGregorio Insurance provides comprehensive guidance through Original Medicare, Medicare Advantage, Supplement, and Part D prescription drug plans. Its service includes annual plan reviews to ensure coverage aligns with changing healthcare needs and assisting clients during enrollment periods. Based in Winthrop, MA, the agency helps local residents evaluate their options for managing medical costs and prescription coverage. It serves single-family homes, apartments, and small businesses throughout the surrounding communities.

WI
4 Putnam St
Winthrop Insurance Inc.
Medicare Insurance Agent · Winthrop, MA

Residents of Winthrop, Massachusetts, who are exploring Medicare coverage options can turn to Winthrop Insurance Inc. for guidance. As a dedicated Medicare insurance agent, the company assists individuals in understanding their healthcare plan choices, including Medicare Advantage and Supplement plans. The agents work to explain coverage details and enrollment timelines clearly. Their services are also available to clients living in the adjacent communities of East Boston and the surrounding Greater Boston metro area, ensuring more local seniors can access professional Medicare insurance assistance.

OI
15-21 Pauline St
OneFuture Insurance MA
Medicare Insurance Agent · Winthrop, MA

Serving Winthrop, Massachusetts, and the surrounding communities, OneFuture Insurance MA specializes in Medicare insurance plans. The agency handles both Medicare Advantage and Medicare supplement options for eligible residents. Its agents work to explain the differences between plan types and coverage details. To handle a typical client situation, the office conducts a personal needs review to identify suitable plan choices before presenting comparisons.

GI
2 Somerset Ave
Gagin Insurance Agency
Medicare Insurance Agent · Winthrop, MA

One-time help with a Medicare plan selection differs from ongoing service that reviews coverage annually. Gagin Insurance Agency assists Winthrop, Massachusetts residents by explaining original Medicare, supplements, and Part D drug plans. A licensed agent clarifies how different options interact with a client’s current coverage and needs. This local office helps individuals compare policies during enrollment periods. For those requiring periodic check-ins rather than a single consultation, service runs on either a scheduled or as-needed basis.

WP
57 Putnam St
Welsh & Parker Insurance Agency
Medicare Insurance Agent · Winthrop, MA

Welsh & Parker Insurance Agency specializes in helping individuals navigate Medicare Advantage and Medicare Supplement plans. It also assists with prescription drug coverage and explains the differences between Original Medicare and private plans. Located in Winthrop, Massachusetts, the agency provides guidance on enrollment periods and plan options tailored to local healthcare needs. This support is particularly valuable during the Annual Enrollment Period each fall, when existing plan changes and new benefits require careful review to avoid coverage gaps or unexpected costs.

BI
207 Hagman Rd
Boyd Insurance Agency
Medicare Insurance Agent · Winthrop, MA

Winthrop seniors searching for clarity during the annual Medicare Open Enrollment period often face complex plan changes. Boyd Insurance Agency in Winthrop, MA, provides local guidance by carefully reviewing each client’s current coverage and anticipated medical needs. The agency helps people understand Part D drug plans, Medicare Advantage options, and supplemental policies that serve the local population. After discussing available networks and potential out-of-pocket costs, a Boyd agent typically coordinates a straightforward assessment of the individual’s prescription list and preferred providers to confirm the best initial-fit choices.

MI
207 Hagman Rd
Meridian Insurance Agency, LLC
Medicare Insurance Agent · Winthrop, MA

Meridian Insurance Agency, LLC serves clients in Winthrop, Massachusetts by providing guidance on Medicare plans and related coverage options. As a local Medicare insurance agent, the company assists individuals with understanding plan benefits. The firm also can help with annual enrollment and subsidy applications. Commercial sectors that the agency can serve include professional offices, warehouses, and food service businesses.

TV
49 Adams St
Terry Vazquez Public Insurance
Medicare Insurance Agent · Winthrop, MA

Terry Vazquez Public Insurance provides Medicare insurance agent services for residents living in and around Winthrop, Massachusetts. For those who own small businesses, the company may also assist with commercial coverage options that complement individual plans. Service extends throughout Winthrop and nearby communities within Suffolk County. The agent helps clients review their current coverage, answering questions about plan changes during enrollment periods. Many clients return for annual policy reviews or to adjust their coverage when health needs shift between regular visits to the office.

NY
207 Hagman Rd
New York Life
Medicare Insurance Agent · Winthrop, MA

New York Life is a company known for assisting Medicare beneficiaries in Winthrop, Massachusetts, with navigating their coverage options. It serves individuals by evaluating different Medicare plans and guiding clients toward appropriate health solutions. This agent helps residents compare prescription drug plans and supplement policies to meet personal healthcare needs. A specialty service it can add on is helping members review annual changes to their existing plans during the Medicare Open Enrollment period.

What Does a 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.

About medicare insurance agents in Winthrop

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.

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.

Are there penalties for late Medicare enrollment in Massachusetts?

Yes. If you do not sign up for Part B when first eligible, you may pay a late enrollment penalty of 10 percent for each full 12-month period you delayed. Massachusetts follows federal rules for these penalties.

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.