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Find Medicare Insurance Agents in Winchester, MA

Browse medicare insurance agents serving Winchester, Massachusetts. Contact information and addresses listed below.

12 agents listed
Updated May 2026
Winchester, 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 12 medicare insurance agents in Winchester, 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.
Scotti Insurance Agency
19 Mt Vernon St, Winchester, MA 01890
(781) 729-9200 scottiinsurance.com
Saltmarsh Insurance Agency
751 Main St, Winchester, MA 01890
(781) 729-4615 saltmarshinsurance.com
John A Pierce Insurance Inc
934 Main St, Winchester, MA 01890
(781) 729-8770 johnpierceinsurance.com
W Allan Wilde & Son Insurance Agency, Inc.
887 Main St #1911, Winchester, MA 01890
(781) 729-1400 wildeinsurance.com
Horace Mann Insurance Co
895 Main St, Winchester, MA 01890
(781) 368-9029 agents.horacemann.com
Furey Insurance
28 Church St #8, Winchester, MA 01890
(781) 721-5758 fureyins.com
BARRY FREEMAN
895 Main St, Winchester, MA 01890
(781) 368-9029 barryfreemaninsurance.com
Barry & McHugh Insurance Inc
10 Skillings Rd, Winchester, MA 01890
(781) 729-6600 barryfinn.com
Stephen Games Public Adjuster
175 Washington St # B12, Winchester, MA 01890
(781) 721-5625
Jay M Finn Insurance
10 Skillings Rd, Winchester, MA 01890
(781) 729-5724 barryfinn.com
Ducey Insurance Agency
10 Skillings Rd, Winchester, MA 01890
(781) 235-6795
Black Horse Insurance
175 Washington St # C24, Winchester, MA 01890
(781) 729-1164 blackhorseinsurance.com

Medicare insurance agents in Winchester Massachusetts help residents navigate Original Medicare Medicare Advantage and Part D drug plans. Massachusetts state law requires all Medicare Supplement plans to be guaranteed issue for eligible beneficiaries during the six-month open enrollment period. Local agents can explain how Winchester providers participate in different plan networks.

What Does a Medicare Insurance Agent in Winchester Cost?

Medicare Part B premiums in 2025 are typically $185 per month for most beneficiaries. Medicare Supplement plans in Massachusetts range from roughly $100 to $300 per month depending on age gender and plan type. Medicare Advantage plans often have $0 monthly premiums but include cost sharing. 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

When can I enroll in Medicare in Winchester?
Your Initial Enrollment Period starts three months before your 65th birthday month and ends three months after. Massachusetts also has a Medicare Supplement open enrollment period that lasts six months from when you first enroll in Part B.
What Medicare plans are available in Winchester Massachusetts?
Winchester residents can choose Original Medicare Medicare Supplement plans Medicare Advantage plans and Part D prescription drug plans. Plan availability varies by carrier and county with Middlesex County offering multiple options.
Do Medicare agents in Winchester charge fees?
Most Medicare insurance agents in Massachusetts are compensated by insurance carriers and do not charge clients directly. Always confirm the agents compensation structure before working with them.