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Find Supplemental Insurance Agents Near You in Madison, WI

Browse supplemental insurance agents serving Madison, Wisconsin. Updated 2026-07-14.

The top-rated supplemental insurance agent in Madison, Wisconsin is Cliff Insurance Agency, Inc, rated 4.9 stars across 1,014 reviews. Other highly rated options include Action Insurance Agency, Winston Financial, Prairie Grove Insurance. This directory lists 18 supplemental insurance agents serving Madison.

Showing 18 supplemental insurance agents in Madison, WIListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Cliff Insurance Agency, Inc2009 W Beltline Hwy Ste 100(608) 203-8585
2Action Insurance Agency2009 W Beltline Hwy Suite 101(608) 222-4555
3Winston Financial34 Schroeder Ct Ste 260(608) 358-3612
4Prairie Grove Insurance5231 Voges Rd(608) 839-0275
5C4 Insurance Services, LLC8446 Excelsior Dr Ste 2(608) 824-7267
6Prairie Land Insurance Agency2045 Atwood Ave Suite 113A(608) 251-3009
7Aria Benefits7818 Big Sky Dr UNIT 104(608) 561-1088
8McClone Insurance - Madison2601 W Beltline Hwy Suite 510(608) 238-2686
9Informed Choice Insurance Agency5325 Wall St Suite 2055(608) 819-6311
10Hausmann Group740 Regent St #400(608) 257-3795
CI
2009 W Beltline Hwy Ste 100
Cliff Insurance Agency, Inc
Supplemental Insurance Agent · Madison, WI

Cliff Insurance Agency, Inc. serves the Madison, Wisconsin metro area as a supplemental insurance agent, helping clients bridge gaps left by major medical plans. These policies cover costs such as deductibles and copays, offering financial protection during health events. The agency assists with selecting coverage that addresses common out-of-pocket expenses not paid by standard health insurance. It regularly handles Medicare supplement plans and hospital indemnity policies, which provide fixed cash benefits for specific medical situations.

AI
2009 W Beltline Hwy Suite 101
Action Insurance Agency
Supplemental Insurance Agent · Madison, WI

Action Insurance Agency in Madison, Wisconsin provides supplemental insurance policies designed to fill coverage gaps left by primary health plans. It offers an array of services including accident, critical illness, and hospital indemnity plans. The agency handles the initial application process and assists customers with claims and policy maintenance throughout the year. It services a variety of properties, such as single-family homes, apartments, retail locations, and restaurants, ensuring these businesses and residences have the necessary extra protection.

WF
34 Schroeder Ct Ste 260
Winston Financial
Supplemental Insurance Agent · Madison, WI

Winston Financial serves homeowners and property managers in Madison, Wisconsin by providing supplemental insurance policies that cover gaps left by standard plans. These policies help clients manage out-of-pocket costs for accidents, critical illness, or hospital stays. The agency guides individuals through available coverage options to suit varying needs and budgets. Winston Financial also extends its supplemental insurance agent services to clients in the adjacent communities of Middleton and Fitchburg.

PG
5231 Voges Rd
Prairie Grove Insurance
Supplemental Insurance Agent · Madison, WI

Prairie Grove Insurance serves Madison, Wisconsin, and its surrounding communities, focusing exclusively on supplemental insurance agent work. It handles policies that help cover gaps left by primary health plans, such as accident, critical illness, and hospital indemnity coverage. The company assists individuals and families in selecting appropriate plans based on their specific needs. To manage a typical job, Prairie Grove Insurance first reviews a client’s existing coverage to identify potential gaps, then presents a limited set of supplemental options for informed comparison.

CI
8446 Excelsior Dr Ste 2
C4 Insurance Services, LLC
Supplemental Insurance Agent · Madison, WI

C4 Insurance Services, LLC in Madison, WI helps individuals assess the difference between one-time supplemental plans, which cover a single event or procedure, and recurring options that provide ongoing support for gaps in primary health insurance. These policies are designed to pay cash directly to the policyholder for expenses like deductibles or co-pays. Appointments and inquiries are handled on a scheduled or as-needed basis to accommodate each client’s specific needs.

PL
2045 Atwood Ave Suite 113A
Prairie Land Insurance Agency
Supplemental Insurance Agent · Madison, WI

Prairie Land Insurance Agency in Madison, WI specializes in supplemental insurance, offering policies that cover gaps left by primary health plans. This agency helps clients manage out-of-pocket expenses from accidents, critical illnesses, and hospital stays. By providing clear explanations of coverage options, it assists individuals in securing financial protection for unforeseen medical events. As winter approaches, the agency guides residents in planning for potential seasonal injuries or unexpected health issues that may arise during the colder months.

AB
7818 Big Sky Dr UNIT 104
Aria Benefits
Supplemental Insurance Agent · Madison, WI

Aria Benefits assists individuals and businesses in Madison with navigating their supplemental insurance needs. The agency focuses specifically on identifying coverage gaps that standard health policies may leave behind. They offer tailored plans designed for non-medical expenses, including accident indemnity, hospital confinement, and critical illness policies. This supplemental coverage can help manage unexpected out-of-pocket costs. Their client base includes a variety of commercial sectors such as local professional offices, warehouse operations, and food service establishments.

MI
2601 W Beltline Hwy Suite 510
McClone Insurance - Madison
Supplemental Insurance Agent · Madison, WI

As winter approaches in Madison, residents often review their health coverage for gaps. McClone Insurance - Madison addresses these concerns as a supplemental insurance agent, helping local clients understand options like accident, critical illness, or hospital indemnity plans. These policies work alongside primary insurance to cover deductibles and out-of-pocket costs. The process begins with a complimentary initial assessment of your existing coverage to identify specific protection needs.

IC
5325 Wall St Suite 2055
Informed Choice Insurance Agency
Supplemental Insurance Agent · Madison, WI

Informed Choice Insurance Agency in Bellevue, WI specializes in providing supplemental coverage that bridges gaps left by primary health plans. Its general service work helps clients manage out-of-pocket expenses and income loss from unexpected medical events. The agency focuses on policies that cover hospital stays, accidents, and critical illnesses. As winter approaches, it assists local residents in preparing for seasonal hazards like slips on ice or flu complications that can result in significant uncovered medical bills.

HG
740 Regent St #400
Hausmann Group
Supplemental Insurance Agent · Madison, WI

Serving Madison, Wisconsin, Hausmann Group provides supplemental insurance to residential clients, helping cover gaps left by major medical plans. Their commercial coverage assists local businesses in offering critical benefits like accident or critical illness protection to employees. Based in the local community, the agency advises customers on policies tailored to individual needs. Agents are available for follow-up service between regular visits, ensuring plan adjustments are handled promptly when life events occur in the household or business.

RM
1241 John Q Hammons Dr
Rural Mutual Insurance Company
Supplemental Insurance Agent · Madison, WI
(608) 836-5525
ruralmutual.com
MI
2921 Landmark Pl Suite 225
Mindful Insurance Agency
Supplemental Insurance Agent · Madison, WI
(608) 338-6445
mindfulinsuranceagency.com
MO
2921 Landmark Pl Suite 420
Mary Olson
Supplemental Insurance Agent · Madison, WI
(608) 819-3674
physiciansmutual.com/agents/Mary_Olson
TB
1001 Fourier Dr #100
Thomas Bradley Insurance
Supplemental Insurance Agent · Madison, WI
(608) 845-7979
thomasbradleyinsurance.com
BR
2921 Landmark Pl Suite 420
Brian Rehm
Supplemental Insurance Agent · Madison, WI
(414) 842-4455
physiciansmutual.com/web/agent/brian_rehm
AF
5610 Medical Cir Ste #9
Affordable Family Insurance
Supplemental Insurance Agent · Madison, WI
(608) 238-5800
affordable-family-insurance.com
FI
7818 Big Sky Dr UNIT 204
Frank Insurance Group
Supplemental Insurance Agent · Madison, WI
(608) 841-1015
frankinsurancewi.com
DH
1277 Deming Way
Dean Health Plan
Supplemental Insurance Agent · Madison, WI
(800) 279-1302
deancare.com

What Does a a Supplemental Insurance Agent in Madison Cost?

Supplemental insurance costs in Wisconsin vary by plan type age and insurer. Medigap Plan G premiums in Madison typically range from 100 to 250 dollars per month for a 65 year old. Costs can be higher for older applicants or those with pre existing conditions. This is general information and not insurance advice.

About supplemental insurance agents in Madison

Supplemental insurance agents in Madison Wisconsin help residents find Medigap and other health coverage to fill gaps in Medicare. Wisconsin law provides special enrollment protections under state statute 632.895. These agents can explain how Wisconsin guaranteed issue rights apply to your situation.

Frequently Asked Questions

What is a supplemental insurance agent in Madison?

A supplemental insurance agent in Madison helps you buy Medigap or other health plans that cover costs not paid by Medicare. They are licensed in Wisconsin and know local insurance options.

When can I enroll in a Medigap plan in Wisconsin?

In Wisconsin you have a six month Medigap open enrollment period starting when you are 65 and enrolled in Medicare Part B. During this time you can buy any Medigap plan without medical underwriting.

Does Wisconsin have special Medigap protections?

Yes Wisconsin law provides guaranteed issue rights for Medigap in certain situations like losing employer coverage. These protections are outlined in Wisconsin statute 632.895 and can help you get a plan without health questions.

Supplemental Insurance Agents in Other Wisconsin Cities

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each supplemental insurance agent's credentials and current standing with your state Department of Insurance.