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Find Medicare Insurance Agents Near You in Boston, MA

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

The top-rated medicare insurance agent in Boston, Massachusetts is Vargas & Vargas Insurance Inc., rated 4.9 stars across 685 reviews. Other highly rated options include Ironside Insurance Group, LLC, Bender Hatch Insurance, Connie Health. This directory lists 19 medicare insurance agents serving Boston.

Showing 19 medicare insurance agents in Boston, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Vargas & Vargas Insurance Inc.1133 Washington St(617) 298-0655
2Ironside Insurance Group, LLC112 Water St #401(617) 227-2400
3Bender Hatch Insurance87 Wendell St 4th Floor(617) 367-4900
4Connie Health99 High St(888) 984-8825
5Click Insurance131 Dartmouth St Fl 3rd, Suite 82(617) 580-3499
6Flynn Insurance Agency30 Park St APT 2(617) 242-1200
7Beacon Hill Insurance Agency200 Portland St(800) 568-4091
8Liberty Mutual Insurance175 Berkeley St(617) 357-9500
9Best Choice Insurance Agency163 Harvard Ave(617) 782-8800
10Uni Life Insurance Agency23 Essex St(857) 576-3957
VV
1133 Washington St
Vargas & Vargas Insurance Inc.
Medicare Insurance Agent · Boston, MA

Vargas & Vargas Insurance Inc. serves the greater Boston, Massachusetts area as a dedicated Medicare insurance agent. It helps individuals navigate the complexities of healthcare coverage, offering guidance on various plan options available to eligible residents. The agency focuses on explaining the differences between Original Medicare and Medicare Advantage. It also assists clients in selecting appropriate prescription drug plans to meet their specific medication needs.

II
112 Water St #401
Ironside Insurance Group, LLC
Medicare Insurance Agent · Boston, MA

Ironside Insurance Group, LLC provides guidance and enrollment support for Medicare insurance plans in Boston, MA. Their services include helping clients understand their coverage options and complete necessary applications. The company offers ongoing policy reviews and annual plan comparisons to ensure needs are met as healthcare requirements change. They assist with navigating Medicare enrollment periods and coordinating benefits. Ironside Insurance Group, LLC serves individual homeowners, families in single-family homes, apartment dwellers, retail business owners, and restaurant operators in the greater Boston area.

BH
87 Wendell St 4th Floor
Bender Hatch Insurance
Medicare Insurance Agent · Boston, MA

Bender Hatch Insurance serves local residents and Medicare-eligible individuals in Boston, MA, helping them navigate the complexities of Medicare insurance options. The company assists clients with plan selection, enrollment, and ongoing coverage management. Its agents provide clear explanations of Original Medicare, Medicare Advantage, and prescription drug plans. Regular reviews ensure policies align with changing health needs and budgets. The agency also extends its Medicare insurance agent services to neighboring communities throughout the greater Boston metro area, including Somerville and Cambridge.

CH
99 High St
Connie Health
Medicare Insurance Agent · Boston, MA

Connie Health, based in Boston, helps clients distinguish between plans requiring a single annual enrollment and policies needing ongoing adjustments. As a Medicare insurance agent in the area, they guide individuals through Part A, Part B, and supplemental options, including prescription drug coverage. They explain how plan benefits change based on health needs and budget. Services are available on a one-time basis for initial enrollment or on an as-needed schedule for future plan reviews and annual changes.

CI
131 Dartmouth St Fl 3rd, Suite 82
Click Insurance
Medicare Insurance Agent · Boston, MA

As Boston’s population ages, many seniors seek reliable guidance through the annual Medicare enrollment period. Click Insurance, a dedicated medicare insurance agent in Boston, Massachusetts, helps clients evaluate their Part D, Medigap, and Advantage options year-round. The agents explain how local plan networks and prescription formularies align with individual health needs and budgets. They also clarify late-enrollment penalties and review any existing coverage for gaps. An initial consultation is conducted in a private meeting to inspect the client’s current plan details and personal health priorities.

FI
30 Park St APT 2
Flynn Insurance Agency
Medicare Insurance Agent · Boston, MA

Flynn Insurance Agency offers specialized guidance in Medicare plan selection, including Medicare Advantage and prescription drug coverage. Serving the Boston, Massachusetts area, the agency assists clients with plan comparisons, enrollment paperwork, and clarifying the differences between Original Medicare and supplemental options. The agent provides ongoing support for annual renewal decisions. This focused service is especially helpful for individuals navigating the initial enrollment period surrounding their 65th birthday or those adjusting coverage during open enrollment season.

BH
200 Portland St
Beacon Hill Insurance Agency
Medicare Insurance Agent · Boston, MA

Beacon Hill Insurance Agency provides Medicare insurance guidance to individuals in the Boston, Massachusetts area. Its work focuses on helping clients understand their health coverage options during enrollment periods and beyond. The company addresses both Medicare Supplement and Medicare Advantage plans, ensuring available choices are clearly explained. It can serve a range of clients, including those managing coverage for small offices and warehouse personnel, as well as workers in the local food service industry.

LM
175 Berkeley St
Liberty Mutual Insurance
Medicare Insurance Agent · Boston, MA

Serving Boston, MA, and the surrounding communities, Liberty Mutual Insurance provides guidance to individuals navigating Medicare options. As a local Medicare insurance agent, the company handles plan comparisons, enrollment periods, and Part D drug coverage details for eligible clients. This firm assists with explaining the differences between Original Medicare and Medicare Advantage plans to help clarify available choices. To approach a typical client case, the agent generally begins with a personalized review of the individual’s healthcare needs and budget before presenting suitable plan solutions from available carriers.

BC
163 Harvard Ave
Best Choice Insurance Agency
Medicare Insurance Agent · Boston, MA

Best Choice Insurance Agency in Boston, MA is known for helping Medicare beneficiaries navigate enrollment periods and plan options. Its service range includes guiding clients through Medicare Supplement, Medicare Advantage, and Part D prescription drug plans. The agency provides personalized consultations to compare coverage choices according to individual healthcare needs. A specialty service it can add on is annual plan review and adjustment assistance for those already enrolled in Medicare.

UL
23 Essex St
Uni Life Insurance Agency
Medicare Insurance Agent · Boston, MA
PI
695 Atlantic Ave
Pilgrim Insurance Co
Medicare Insurance Agent · Boston, MA
(617) 956-6000
plymouthrock.com
1C
75 Orleans St
1st Choice Insurance MA
Medicare Insurance Agent · Boston, MA
(351) 203-0436
AI
1065 Commonwealth Ave # 3
Allston Insurance Agency, Inc.
Medicare Insurance Agent · Boston, MA
(617) 562-8200
allstoninsuranceagency.com
UF
77 Warren St
US Family Health Plan at Brighton Marine
Medicare Insurance Agent · Boston, MA
(800) 818-8589
usfamilyhealth.org
AH
100 Pier 4 Blvd.
Adelphi Health Insurance
Medicare Insurance Agent · Boston, MA
(413) 450-0388
OC
121 Tremont St
One Call Insurance
Medicare Insurance Agent · Boston, MA
(617) 782-2255
onecallinsurance.com
TM
346 Commercial St
Thrive Medicare Strategies
Medicare Insurance Agent · Boston, MA
(860) 680-1708
SI
123 Beach St
Sterling Insurance Group of Boston
Medicare Insurance Agent · Boston, MA
(508) 687-2750
insurewithsterling.com
CM
33 Essex St #1
Compare Medicare Insurance
Medicare Insurance Agent · Boston, MA
(617) 544-3752

What Does a a Medicare Insurance Agent in Boston Cost?

Medicare insurance agents in Massachusetts generally do not charge clients directly. Their compensation comes from insurance companies as commissions. These commissions are built into plan premiums and do not increase your out of pocket costs. For Medigap plans premiums in Boston can range from about 100 to 400 dollars per month depending on age gender and plan type. Costs for Medicare Advantage plans vary by carrier and county. This is general information not insurance advice.

About medicare insurance agents in Boston

Medicare insurance agents in Boston Massachusetts help residents compare plans and enroll in coverage that fits their needs. Massachusetts has its own Medigap rules including guaranteed issue rights for certain enrollees. Agents licensed in the state must follow Massachusetts Division of Insurance regulations and can assist with Medicare Advantage Part D and Supplement plans.

Frequently Asked Questions

What does a Medicare insurance agent in Boston do?

A Medicare insurance agent helps you review plan options compare costs and enroll in Medicare Advantage Part D or Medigap plans. They are licensed in Massachusetts and can explain how local networks and formularies work.

When can I enroll in Medicare in Massachusetts?

The Initial Enrollment Period starts three months before your 65th birthday month and ends three months after. Massachusetts also has an Annual Enrollment Period from October 15 to December 7 and a Medicare Advantage Open Enrollment from January 1 to March 31.

Are Medicare agents in Boston free to use?

Most Medicare insurance agents are paid by insurance carriers so their services are typically free to you. They do not charge a fee for helping you compare plans or enroll. Always confirm the agents compensation model before working with them.

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.