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Find Medicare Insurance Agents Near You in Middleton, WI

Browse medicare insurance agents serving Middleton, Wisconsin. Updated 2026-07-14.

The top-rated medicare insurance agent in Middleton, Wisconsin is The Health Insurance Store, rated 5.0 stars across 1,125 reviews. Other highly rated options include Compliance Insurance, Baer Insurance Services, Inc., AVID Risk Solutions. This directory lists 17 medicare insurance agents serving Middleton.

Showing 17 medicare insurance agents in Middleton, WIListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1The Health Insurance Store7447 University Ave Suite 204(608) 210-2500
2Compliance Insurance8383 Greenway Blvd 6th Floor, Ste 600(608) 836-1001
3Baer Insurance Services, Inc.9701 Brader Way Suite 101(608) 830-5800
4AVID Risk Solutions2501 Parmenter St #200a(608) 827-4525
5Schwarz Insurance Agency6605 University Ave Suite 202(608) 831-9660
6Jeff Engelkes Agency, Inc. American Family Insurance1468 N High Point Rd # 101(608) 831-1800
7Daniel Olson American Family Insurance1833 Parmenter St(608) 836-4200
8Michael Donnelly: Allstate Insurance6661 University Ave Ste 108(608) 729-0147
9Brian Kelly Agency, LLC American Family Insurance6700 University Ave(608) 831-2525
10Dan Pechauer - State Farm Insurance Agent6926 University Ave(608) 831-3393
HI
7447 University Ave Suite 204
The Health Insurance Store
Medicare Insurance Agent · Middleton, WI

The Health Insurance Store serves the Middleton, Wisconsin area and the broader Dane County region as a local Medicare insurance agent. This agency helps clients navigate Medicare plans, including Medicare Advantage and Medicare Supplement policies. The staff works to explain enrollment timelines and coverage options to elderly residents. They assist with comparing Part D prescription drug plans and will review both network and cost differences between available policies. The Health Insurance Store provides help with Medicare Supplement and Medicare Advantage plan selection.

CI
8383 Greenway Blvd 6th Floor, Ste 600
Compliance Insurance
Medicare Insurance Agent · Middleton, WI

Located in Middleton, Wisconsin, Compliance Insurance offers enrollment assistance for Medicare Advantage, Supplement, and Part D prescription drug plans. It provides ongoing plan reviews and annual updates to help clients adapt to changing healthcare needs. This independent agency focuses on explaining coverage differences and guiding individuals through open enrollment without high-pressure tactics. For local residents, it conducts personalized consultations to match plans with medical and financial situations. Compliance Insurance serves single-family homes, apartments, and assisted living facilities within the Middleton area.

BI
9701 Brader Way Suite 101
Baer Insurance Services, Inc.
Medicare Insurance Agent · Middleton, WI

For homeowners and retirees in Middleton, Baer Insurance Services, Inc. provides personalized guidance on Medicare insurance options. The agency helps clients understand Medicare Advantage, supplement, and Part D prescription drug plans. Its agents compare available local carriers to simplify the enrollment process. The business focuses on finding coverage that fits individual healthcare needs and budgets. Baer Insurance Services also serves seniors in surrounding Dane County communities such as Madison.

AR
2501 Parmenter St #200a
AVID Risk Solutions
Medicare Insurance Agent · Middleton, WI

Based in Middleton, Wisconsin, AVID Risk Solutions serves clients throughout the Madison area and surrounding Dane County communities to navigate their Medicare coverage. The company handles both Medicare Supplement and Medicare Advantage plan options, assisting beneficiaries when they become newly eligible for benefits. Each case is reviewed against the individual’s current healthcare needs and budget expectations. Standard practice involves scheduling a localized consultation, reviewing available plan choices side by side, and helping the client finalize a selection at no cost.

SI
6605 University Ave Suite 202
Schwarz Insurance Agency
Medicare Insurance Agent · Middleton, WI

Schwarz Insurance Agency in Middleton, WI distinguishes between offering guidance for a one-time plan selection and providing recurring annual reviews of coverage. As a medicare insurance agent, the firm helps individuals navigate the differences between Medicare Supplement and Medicare Advantage plans. The goal is to align a client's healthcare needs with available local and national options. Service is available on an as-needed basis, with additional support typically offered during the Annual Enrollment Period for any necessary adjustments.

JE
1468 N High Point Rd # 101
Jeff Engelkes Agency, Inc. American Family Insurance
Medicare Insurance Agent · Middleton, WI

Jeff Engelkes Agency, Inc. American Family Insurance specializes in guiding Medicare beneficiaries through plan selection, helping clients compare Medicare Advantage, Supplement, and Part D prescription drug options to match their healthcare needs in Middleton, WI. The agency also provides ongoing support for understanding changing plan benefits, network updates, and coverage adjustments. During the annual Medicare Open Enrollment period, it assists local residents in reviewing and modifying their existing plans to avoid gaps in coverage due to evolving health conditions or drug costs.

DO
1833 Parmenter St
Daniel Olson American Family Insurance
Medicare Insurance Agent · Middleton, WI

As the Medicare Annual Enrollment Period approaches each fall, residents of the Middleton, WI area often face complex coverage decisions. Daniel Olson American Family Insurance provides local guidance on plan options for both initial enrollment and annual changes, clarifying the differences between Medicare Advantage, supplements, and Part D drug plans. Agents work directly with clients to review current healthcare needs, ensuring each recommendation aligns with individual preferences. The first step for any client unsure of their best path forward is to schedule a free, no-obligation plan review session.

MD
6661 University Ave Ste 108
Michael Donnelly: Allstate Insurance
Medicare Insurance Agent · Middleton, WI

Michael Donnelly: Allstate Insurance serves residents of Middleton with Medicare insurance guidance, helping clients understand their coverage options for hospital and medical needs. Commercial coverage is also available for local businesses seeking employee benefits or group plans. The service area extends throughout the Middleton region, ensuring convenient access for policy questions and plan adjustments. Agent Michael Donnelly provides ongoing support between regular visits, assisting with annual enrollment changes or claim follow-up.

BK
6700 University Ave
Brian Kelly Agency, LLC American Family Insurance
Medicare Insurance Agent · Middleton, WI

Brian Kelly Agency, LLC American Family Insurance assists individuals with healthcare coverage by focusing on Medicare insurance plans in Middleton, Wisconsin. The agency helps clients navigate plan selections, including parts A, B, and supplemental options, to match their medical needs and budgets. Its work regularly serves local professionals in office environments, supports employees in warehouse operations, and aids those working in food service establishments throughout the area.

DP
6926 University Ave
Dan Pechauer - State Farm Insurance Agent
Medicare Insurance Agent · Middleton, WI

Dan Pechauer - State Farm Insurance Agent in Middleton, WI, is known for providing guidance on Medicare insurance plans. The company assists local clients in understanding their coverage options during enrollment periods and beyond. Services include explaining the differences between Medicare Supplement and Medicare Advantage plans. The agency also addresses ongoing policy questions and helps with annual plan reviews. A specialty service it can add on is helping clients coordinate their Medicare benefits with existing life insurance policies.

PI
2421 Parmenter St
Petersburg Insurance Agency LLC
Medicare Insurance Agent · Middleton, WI
(608) 824-7267
c4ins.com
RI
1818 Parmenter St #300
Riesen Insurance Agency, LLC
Medicare Insurance Agent · Middleton, WI
(608) 225-3523
teamriesen.com
SI
9701 Brader Way
Success Insurance Now
Medicare Insurance Agent · Middleton, WI
(608) 291-4098
SI
1800 Deming Way
Sentry Insurance – Middleton Regional Office
Medicare Insurance Agent · Middleton, WI
(800) 473-6879
sentry.com
GN
6810 University Ave
Greene-Niesen Insurance Agency, Inc.
Medicare Insurance Agent · Middleton, WI
(608) 831-3168
greeneniesen.com
GI
2501 Parmenter St #200a
Gallagher Insurance, Risk Management & Consulting
Medicare Insurance Agent · Middleton, WI
(608) 827-4525
locations.ajg.com/us/wi/middleton/2501-parmenter-street
IH
1600 Aspen Commons #600
Independent Health Care Plan (iCare)
Medicare Insurance Agent · Middleton, WI
(800) 777-4376
icarehealthplan.org

What Does a a Medicare Insurance Agent in Middleton Cost?

Medicare insurance agents in Wisconsin are typically paid by insurance companies so you do not pay a fee for their services. Medicare Part B premiums are set by the federal government at $174.70 per month for most people in 2024. Costs for Medicare Advantage and Part D plans vary by carrier and county with monthly premiums ranging from $0 to over $100. This is general information and not insurance advice.

About medicare insurance agents in Middleton

Medicare insurance agents in Middleton Wisconsin help residents compare Medicare Advantage and Supplement plans. Wisconsin law requires agents to be licensed by the Office of the Commissioner of Insurance. Local agents understand the specific network options available in Dane County.

Frequently Asked Questions

What does a Medicare insurance agent in Middleton do?

A Medicare insurance agent helps you review your health needs and compare Medicare plans. They explain the differences between Original Medicare Medicare Advantage and Part D drug plans. They do not charge you directly as they are paid by insurance carriers.

When can I enroll in Medicare in Wisconsin?

Your Initial Enrollment Period starts three months before you turn 65 and ends three months after your birthday month. Wisconsin also has a Annual Enrollment Period from October 15 to December 7 each year. Special Enrollment Periods are available for certain life events like moving or losing other coverage.

Does a Medicare agent help with Wisconsin BadgerCare?

No Medicare agents do not help with BadgerCare which is Wisconsin Medicaid. BadgerCare is for low-income individuals and families. Medicare agents only assist with Medicare plans for people age 65 and older or those with certain disabilities.

Medicare Insurance Agents in Other Wisconsin Cities

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