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Find Supplemental Insurance Agents in Wellesley, MA

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

11 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 11 supplemental 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
Shining Insurance LLC
277 Linden St, Wellesley, MA 02482
(781) 757-1097
Happily Insured
1 Washington St # 105, Wellesley, MA 02481
(351) 203-0257
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
Cochrane & Porter Insurance Agency
981 Worcester St, Wellesley, MA 02482
(781) 943-1555 cochraneandporter.com

Supplemental insurance agents in Wellesley Massachusetts help residents find Medigap plans and other health coverage options. Massachusetts state law provides a six-month open enrollment period for Medicare Supplement plans when you first turn 65. Local agents can guide you through the specific rules and plan choices available in Wellesley and the surrounding area.

What Does a Supplemental Insurance Agent in Wellesley Cost?

Supplemental insurance agent services in Massachusetts are typically free to you because the agent earns a commission from the insurance company. Medigap plan premiums in Wellesley can range from about 100 to 300 dollars per month depending on your age health and the plan type. Costs vary by carrier and plan level. 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 Wellesley?
A supplemental insurance agent in Wellesley helps you compare and enroll in Medicare Supplement plans also called Medigap. These agents are licensed in Massachusetts and understand local insurance carriers and plan options.
When can I enroll in a Medigap plan in Massachusetts?
In Massachusetts you have a six-month open enrollment period that starts when you are both 65 and enrolled in Medicare Part B. During this time you can buy any Medigap policy without medical underwriting. After this period you may face health questions or higher rates.
How do I choose a supplemental insurance agent in Wellesley?
Look for an agent licensed in Massachusetts with experience in Medicare Supplement plans. Ask about the carriers they represent and whether they offer free consultations. You can verify an agents license through the Massachusetts Division of Insurance website.