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Find Medicare Insurance Agents Near You in Cheshire, CT

Directory of medicare insurance agents in Cheshire, Connecticut. Verify credentials with the state department of insurance before hiring.

14 agents listed
Updated May 2026
Cheshire, CT
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 Connecticut before hiring.
Showing 14 medicare insurance agents in Cheshire, CT Listings are displayed in no particular order and are not ranked by BeforeInsuranceUSA. Order does not constitute a recommendation or endorsement of any agent.
Derek Gromko - State Farm Insurance Agent
366 S Main St, Cheshire, CT 06410
(203) 439-2386 derekgromko.com
Relation Insurance Services
55 Realty Dr # 305, Cheshire, CT 06410
(203) 250-1006 relationinsurance.com
HUB International
1520 Highland Ave, Cheshire, CT 06410
(203) 439-2815 hubinternational.com
Arisco Insurance Group
55 Elm St Suite 2, Cheshire, CT 06410
(203) 379-7852 ariscoinsurancegroup.com
The Newton Agency, LLC: Allstate Insurance
629 S Main St, Cheshire, CT 06410
(203) 272-2200 agents.allstate.com
Anthony Gargano - State Farm Insurance Agent
558 Maple Ave # 1, Cheshire, CT 06410
(203) 874-0676 tonygarg.com
Cheshire Insurance and Travels
1065 S Main St c, Cheshire, CT 06410
(203) 439-8994
Bristol Insurance Inc
195 S Main St, Cheshire, CT 06410
(203) 272-3567
New England Insurance Group/ David J. Isenstadt, CIC
365 Highland Ave STE 101, Cheshire, CT 06410
(203) 250-1135 neinsurancegroup.com
A Zagar Insurance
1157 Highland Ave # 110, Cheshire, CT 06410
(203) 272-8112
Alliant Insurance Services, Inc.
55 Realty Dr #200, Cheshire, CT 06410
(203) 756-8061 alliant.com
Medicare Services CT
1120 S Main St, Cheshire, CT 06410
(860) 803-1633 medicarefreeservicect.com
Medicare Options 101 at The Cheshire Agency
615 W Johnson Ave, Cheshire, CT 06410
(203) 250-9099 medicareoptions101.com
Benefits Group
700 W Johnson Ave #301, Cheshire, CT 06410
(877) 250-7880 thebenefitsgroupofct.com

Medicare insurance agents in Cheshire, Connecticut help residents compare Medicare Advantage, Medigap, and Part D plans. Connecticut law requires agents to be licensed by the state and follow strict marketing guidelines. Local agents understand the specific plan options available in New Haven County and can guide you through Initial Enrollment or the Annual Enrollment Period.

What Does a Medicare Insurance Agent in Cheshire Cost?

Medicare insurance agents in Connecticut typically do not charge you directly for their services. They are paid commissions by the insurance companies whose plans they sell. Plan premiums vary widely: Medicare Advantage plans may have $0 monthly premiums, while Medigap plans in Connecticut can range from $100 to $300 per month depending on your age and health status. Part D prescription drug plans usually cost between $10 and $80 per month. 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

When can I enroll in Medicare in Cheshire Connecticut?
Your Initial Enrollment Period begins three months before you turn 65 and ends three months after your birthday month. Connecticut also follows the federal Annual Enrollment Period from October 15 to December 7 each year. Special Enrollment Periods are available for certain life events like moving or losing employer coverage.
What types of Medicare plans are available in Cheshire Connecticut?
Cheshire residents can choose Original Medicare, Medicare Advantage plans, Medigap supplemental plans, and Part D prescription drug plans. Connecticut offers a variety of Medicare Advantage HMO and PPO options through private insurers. Medigap plans are standardized by letter and must follow Connecticut state rules.
How do I choose a Medicare insurance agent in Cheshire Connecticut?
Look for an agent licensed in Connecticut who represents multiple insurance carriers. Ask about their experience with Medicare plans in New Haven County. A good agent will explain plan differences without pressuring you and help you compare costs and coverage.