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Medicare Insurance Agents in Wellesley, MA

Compare medicare insurance agents in Wellesley. Review contact information and insurance categorys before you decide.

13 agents listed
Updated May 2026
Wellesley, 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 13 medicare insurance agents in Wellesley, 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.
Deland, Gibson Insurance Associates — Wellesley Hills
36 Washington St #40, Wellesley, MA 02481
(781) 237-1515 delandgibson.com
Cross Insurance
287 Linden St, Wellesley, MA 02482
(781) 235-3100 crossagency.com
CAV Insurance Agency, Inc.
40 Grove St #260, Wellesley, MA 02482
(781) 237-4107 cavinsurance.com
Happily Insured
1 Washington St # 105, Wellesley, MA 02481
(351) 203-0257
Shining Insurance LLC
277 Linden St, Wellesley, MA 02482
(781) 757-1097
Harvard Pilgrim Health Care
93 Worcester St, Wellesley, MA 02481
(888) 333-4742 harvardpilgrim.org
Sun Life
96 Worcester St, Wellesley, MA 02481
(781) 237-6030 sunlife.com
Hoffman Insurance Services, Inc.
148 Linden St Suite 300, Wellesley, MA 02482
(781) 235-0087 hoffmaninsurance.com
Page & Lugton Insurance Agency
31 Washington St, Wellesley, MA 02481
(781) 444-0853 cavinsurance.com
Insurance Services of New England
148 Linden St Suite 300, Wellesley, MA 02481
(844) 386-8730 isne-llc.com
Drislane & Mastroianni Brokerage
267 Washington St #4, Wellesley, MA 02481
(800) 227-1258 dandmbrokerage.com
MMA
981 Worcester St, Wellesley, MA 02482
(781) 235-0708
Global Insurance Services Ltd
62 Walnut St, Wellesley, MA 02481
(781) 997-0670

What Does a Medicare Insurance Agent in Wellesley Cost?

Medicare insurance agents in Massachusetts are typically paid by insurance companies so you do not pay a fee for their services. Medigap plan premiums in Wellesley can range from about 100 to 300 dollars per month depending on age gender and plan type. Medicare Advantage plans often have low or zero monthly premiums but may have copays and deductibles. This is general information and 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 Wellesley do?
A Medicare insurance agent helps you review and enroll in Medicare plans such as Part D drug plans Medicare Advantage or Medigap. They work with multiple carriers to show you options that fit your needs and budget.
Do I need a special enrollment period in Massachusetts?
Massachusetts follows federal Medicare enrollment periods. You have an Initial Enrollment Period when you turn 65 and an Annual Enrollment Period from October 15 to December 7. Special Enrollment Periods may apply if you move or lose other coverage.
Can a Medicare agent help me with Medigap plans in Massachusetts?
Yes. Agents can explain Medigap plans A through N which are standardized in Massachusetts. They can help you compare premiums and benefits. Massachusetts does not require guaranteed issue for Medigap outside of certain situations.