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Supplemental Insurance Agents in Winchester, MA

Compare supplemental insurance agents in Winchester. Review contact information and insurance categorys before you decide.

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 supplemental 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
Admiralty Insurance Agency Inc
2 Central St, Winchester, MA 01890
(781) 721-5500 admiraltyinsurance.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
Jay M Finn Insurance
10 Skillings Rd, Winchester, MA 01890
(781) 729-5724 barryfinn.com
Black Horse Insurance
175 Washington St # C24, Winchester, MA 01890
(781) 729-1164 blackhorseinsurance.com
Ducey Insurance Agency
10 Skillings Rd, Winchester, MA 01890
(781) 235-6795

Supplemental insurance agents in Winchester, Massachusetts help residents navigate Medicare Supplement plans, Medicare Advantage, and other gap coverage. Massachusetts has a unique Medigap open enrollment period that starts when you turn 65 and enroll in Medicare Part B. Local agents can explain how state regulations like the guaranteed issue rules apply to your situation.

What Does a Supplemental Insurance Agent in Winchester Cost?

Supplemental insurance costs in Massachusetts vary by plan type, age, and insurer. Medigap Plan G premiums for a 65-year-old in Winchester typically range from $120 to $250 per month. Medicare Advantage plans may have $0 premiums but include out-of-pocket costs. Costs can change annually. 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 Winchester?
A supplemental insurance agent in Winchester helps you find policies that cover costs not paid by Original Medicare, such as copayments and deductibles. They are licensed in Massachusetts and can explain Medigap plans standardized by the state.
When can I enroll in a Medigap plan in Massachusetts?
In Massachusetts, you have a six-month Medigap open enrollment period that begins the month you are 65 and enrolled in Medicare Part B. During this time, insurers cannot deny you coverage or charge higher premiums due to pre-existing conditions.