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Find Medicare Insurance Agents Near You in Sheboygan, WI

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

20 agents listed
Updated May 2026
Sheboygan, WI
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 Wisconsin before hiring.
Showing 20 medicare insurance agents in Sheboygan, WI Listings are displayed in no particular order and are not ranked by BeforeInsuranceUSA. Order does not constitute a recommendation or endorsement of any agent.
Acuity Insurance
2800 S Taylor Dr, Sheboygan, WI 53081
(800) 242-7666 acuity.com
Patch Adams Medicare Solutions
615 S 8th St Suite 120, Sheboygan, WI 53081
(920) 395-1404 patchadamsmedicare.com
Sue Breitbach Fenn Agency LLC American Family Insurance
3626 Erie Ave, Sheboygan, WI 53081
(920) 457-1950 amfam.com
Allstate Insurance Agent Jerry Bodart
909 N 8th St UNIT 105, Sheboygan, WI 53081
(920) 547-5724 agents.allstate.com
Aim Group Inc.
526 N 8th St, Sheboygan, WI 53081
(920) 457-9112 aimgroupinsurance.com
J M Sampson Agency LLC American Family Insurance
2204 Wilson Ave Ste 2, Sheboygan, WI 53081
(920) 452-3661 amfam.com
Amy Gabrielse Agency, Inc American Family Insurance
2108 Kohler Memorial Dr Ste 200, Sheboygan, WI 53081
(920) 458-2101 amfam.com
Blia Vang - State Farm Insurance Agent
3005 S 12th St, Sheboygan, WI 53081
(920) 452-2482 bliavang.com
Abby Wilterdink Agency LLC American Family Insurance
601 Center Ave, Sheboygan, WI 53081
(920) 459-9919 amfam.com
Heinen & Associates
1601 N 8th St, Sheboygan, WI 53081
(920) 458-9724 heineninsurance.com
Key Insurance Services Inc
1019 Michigan Ave, Sheboygan, WI 53081
(920) 458-8400 keyinsuranceinc.com
Brandl Insurance Agency Sheboygan
801 N 8th St, Sheboygan, WI 53081
(920) 457-3743 brandlinsurance.com
Boll Insurance Agency, inc.
1424 Union Ave, Sheboygan, WI 53081
(920) 457-7386 bollinsuranceagency.net
McClone Insurance - Sheboygan
833 Pennsylvania Ave, Sheboygan, WI 53081
(920) 458-6174 mcclone.com
Kenny Martinson - COUNTRY Financial Agent
701 N 8th St, Sheboygan, WI 53081
(920) 636-2991 agents.countryfinancial.com
Ansay & Associates LLC
902 Michigan Ave, Sheboygan, WI 53081
(920) 457-9035 ansay.com
Tetschlag Financial Services
731 Pennsylvania Ave, Sheboygan, WI 53081
(920) 335-8374
Great Insurance Service WI
1526 S 12th St, Sheboygan, WI 53081
(920) 659-5592
Trempe Insurance Agency
1414 N Taylor Dr #105, Sheboygan, WI 53081
(920) 452-9483 trempeinsuranceagency.com
Circle Insurance Service, Inc
1414 N Taylor Dr #105, Sheboygan, WI 53081
(920) 458-0321 circleinsurance.com

Medicare insurance agents in Sheboygan, Wisconsin help residents compare Medicare Advantage, Medigap, and Part D plans. Under Wisconsin law, agents must be licensed by the Office of the Commissioner of Insurance and follow strict marketing rules. They can assist with Initial Enrollment Periods, Annual Enrollment Periods, and Special Enrollment Periods based on your situation.

What Does a Medicare Insurance Agent in Sheboygan Cost?

Medicare insurance agent services in Sheboygan are usually free to you because the agent receives a commission from the insurance carrier. Commission amounts vary by plan type and carrier, but typical commissions range from $200 to $600 per enrollment for Medicare Advantage or Part D plans. For Medigap plans, commissions are often lower and paid annually. Costs are not charged directly to you unless you agree to a fee arrangement. 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 does a Medicare insurance agent in Sheboygan do?
A Medicare insurance agent helps you review plan options, explain coverage details, and enroll in a plan that fits your needs. They work with multiple carriers and must follow Wisconsin regulations, including no unsolicited door-to-door sales.
When can I enroll in Medicare in Sheboygan?
Your Initial Enrollment Period starts three months before you turn 65 and ends three months after. The Annual Enrollment Period runs from October 15 to December 7 each year. Wisconsin also has a Medigap Open Enrollment Period that lasts six months starting when you first enroll in Part B.
Are Medicare insurance agent services free in Sheboygan?
Most Medicare insurance agents are paid by the insurance companies, not by you. Their services are typically free to you. However, some agents may charge a fee for certain services, so always ask about costs before working with them.