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Find Medicare Insurance Agents Near You in Pewaukee, WI

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

The top-rated medicare insurance agent in Pewaukee, Wisconsin is Brandi Wein - State Farm Insurance Agent, rated 5.0 stars across 40 reviews. Other highly rated options include American Advantage Insurance - Lindow Agency, First Insurance Solutions, Security Insurance Agency, Inc.. This directory lists 13 medicare insurance agents serving Pewaukee.

Showing 13 medicare insurance agents in Pewaukee, WIListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Brandi Wein - State Farm Insurance AgentN27W23957 Paul Rd Ste 101(262) 544-1800
2American Advantage Insurance - Lindow Agency2311 Silvernail Rd(262) 398-9529
3First Insurance Solutions2835 N Grandview Blvd Suite 200(262) 521-0900
4Security Insurance Agency, Inc.131 E Wisconsin Ave #102(262) 691-4800
5Sage Insurance GroupN27 W23960 Paul Rd Suite 5(262) 737-5080
6Wisdom Insurance Agency, Inc2309 W Silvernail Rd(262) 408-5019
7Quotes Insurance Agency1850A Meadow Ln(715) 201-4447
8Fast Insurance WI617 Ryan St(715) 201-4206
9Capital-Richter Insurance Services1099 Quail Ct Ste 210(262) 691-4100
10Cowles Insurance Services LLC325 Forest Grove Dr Suite 100(262) 333-8119
BW
N27W23957 Paul Rd Ste 101
Brandi Wein - State Farm Insurance Agent
Medicare Insurance Agent · Pewaukee, WI

Brandi Wein - State Farm Insurance Agent serves the Pewaukee, Wisconsin area and surrounding Waukesha County. As a Medicare insurance agent, the company helps individuals navigate their health coverage options during enrollment periods. The business offers guidance on plan selection, coverage details, and policy changes. Clients can receive assistance with initial enrollment in Medicare Part A and Part B, as well as comparing Medicare Supplement and Medicare Advantage plans to meet specific healthcare needs.

AA
2311 Silvernail Rd
American Advantage Insurance - Lindow Agency
Medicare Insurance Agent · Pewaukee, WI

American Advantage Insurance - Lindow Agency provides a full range of Medicare insurance agent services, including plan comparisons and enrollment support for clients in Pewaukee, Wisconsin. It offers ongoing service and maintenance plans that assist with annual plan reviews and claims guidance. The agency helps individuals navigate Medicare options throughout the season to maintain appropriate coverage. It services single-family homes, apartments, retail locations, and restaurants.

FI
2835 N Grandview Blvd Suite 200
First Insurance Solutions
Medicare Insurance Agent · Pewaukee, WI

Pewaukee residents needing coverage around retirement age can work with First Insurance Solutions, a Medicare insurance agent in this area. The agency assists older adults and those eligible for Medicare by explaining plan options and helping with enrollments. It provides guidance on both medical and prescription drug coverage to help clients navigate their choices. Supporting local homeowners in Waukesha County, the agency bridges the gap between federal benefits and individual needs. It also serves clients in the neighboring community of Brookfield.

SI
131 E Wisconsin Ave #102
Security Insurance Agency, Inc.
Medicare Insurance Agent · Pewaukee, WI

Security Insurance Agency, Inc. serves the Pewaukee, Wisconsin area and surrounding communities, handling Medicare health plan selection and enrollment for local residents. The agency works to guide individuals through the complexities of Medicare options including Advantage plans and prescription drug coverage. It takes a straightforward, consultative approach to each client engagement, focusing on understanding personal health care needs and budget requirements before presenting available plan choices from multiple insurers to ensure an appropriate fit.

SI
N27 W23960 Paul Rd Suite 5
Sage Insurance Group
Medicare Insurance Agent · Pewaukee, WI

Sage Insurance Group, located in Pewaukee, Wisconsin, offers Medicare insurance clients a choice between one-time annual enrollment reviews or ongoing coverage management. The agency helps individuals understand and compare Medicare Advantage, supplement, and Part D prescription drug plans that meet their specific healthcare and budget needs. Their work is local, focusing on guiding clients through plan changes and deadlines without high-pressure sales tactics. This assistance is available on a one-time, scheduled, or as-needed basis.

WI
2309 W Silvernail Rd
Wisdom Insurance Agency, Inc
Medicare Insurance Agent · Pewaukee, WI

Specializing in Medicare Advantage, Supplement, and Part D prescription drug plans, Wisdom Insurance Agency, Inc. in Pewaukee, Wisconsin helps clients navigate their coverage options each year. The agency works individually with beneficiaries to compare plans from multiple carriers, focusing on aligning costs with personal health care needs. It also assists with enrollment during Initial Coverage Election Periods and addresses questions about plan changes during the Medicare Annual Enrollment Period each fall.

QI
1850A Meadow Ln
Quotes Insurance Agency
Medicare Insurance Agent · Pewaukee, WI

As the Medicare Annual Enrollment Period approaches each fall, many Pewaukee residents find evaluating their options confusing. Quotes Insurance Agency helps individuals understand their coverage choices and navigate plan changes with straightforward guidance. Whether a client is new to Medicare or reviewing existing coverage for the upcoming year, the agency explains how different plans work in local healthcare networks. This process makes selecting a suitable policy clear rather than overwhelming, beginning with a simple conversation to review each person’s current situation before scheduling an initial in-person or phone assessment.

FI
617 Ryan St
Fast Insurance WI
Medicare Insurance Agent · Pewaukee, WI

Fast Insurance WI helps individuals understand their Medicare options and enroll in suitable plans. As a dedicated Medicare insurance agent in Pewaukee, WI, the company assists clients with navigating Original Medicare, Medicare Advantage, and prescription drug coverage. They focus on matching local residents with appropriate supplemental policies. Businesses and organizations in the area can consult the agency for Medicare-related services, including those for office buildings, warehouses, and food service facilities.

CR
1099 Quail Ct Ste 210
Capital-Richter Insurance Services
Medicare Insurance Agent · Pewaukee, WI

Capital-Richter Insurance Services in Pewaukee, Wisconsin assists clients with both initial enrollment into a Medicare plan and ongoing adjustments to coverage as needs change. Navigating annual open enrollment, plan changes, and supplement options can require periodic professional review. Interim consultations may also be appropriate when unexpected health or financial shifts occur. The agency offers these Medicare Insurance Agent services on a one-time, scheduled, or as-needed basis depending on the client’s preference and current situation.

CI
325 Forest Grove Dr Suite 100
Cowles Insurance Services LLC
Medicare Insurance Agent · Pewaukee, WI

Cowles Insurance Services LLC offers residential Medicare insurance guidance to individuals in Pewaukee, Wisconsin. Commercial coverage assistance is also available, with service extending throughout the local area and surrounding communities. Clients receive help understanding plan options and enrollment periods. The agent provides follow-up support between regular annual visits, ensuring coverage remains aligned with changing health needs and prescription requirements throughout the year.

MS
N27W23953 Paul Rd Suite 200
Midwest Select Insurance Group (MSIG)
Medicare Insurance Agent · Pewaukee, WI
(715) 309-5495
ms-ig.com
SI
2114 Silvernail Rd
Spectrum Insurance Group - Milwaukee
Medicare Insurance Agent · Pewaukee, WI
(888) 368-8630
spectruminsgroup.com
AA
353 Forest Grove Dr Suite 205
American Advantage - IFS
Medicare Insurance Agent · Pewaukee, WI
(262) 696-5800
aaigifs.com

What Does a a Medicare Insurance Agent in Pewaukee Cost?

Medicare insurance agent services in Wisconsin are usually free to you because the agent earns a commission from the insurance carrier. Commissions vary by plan type and company, typically ranging from 0 to 600 dollars per year for a new policy. Some agents may charge a consultation fee, but that is uncommon. This is general information and not insurance advice.

About medicare insurance agents in Pewaukee

Medicare insurance agents in Pewaukee, Wisconsin help residents compare Part D, Medicare Advantage, and Medigap plans. Wisconsin state law requires agents to be licensed and follow specific marketing guidelines set by the Office of the Commissioner of Insurance. Local agents understand the health care providers and coverage options available in Waukesha County.

Frequently Asked Questions

When can I enroll in Medicare in Pewaukee Wisconsin?

The Initial Enrollment Period starts three months before your 65th birthday and ends three months after. Wisconsin also has a Annual Enrollment Period from October 15 to December 7 each year. Special Enrollment Periods may apply if you lose other coverage.

Do Medicare agents in Wisconsin charge a fee?

Most Medicare insurance agents in Wisconsin are paid by the insurance companies they represent, not by you. They typically do not charge a direct fee for helping you enroll. Always confirm the payment arrangement before working with an agent.

What is the difference between Medicare Advantage and Medigap in Wisconsin?

Medicare Advantage plans replace Original Medicare and often include drug coverage. Medigap plans supplement Original Medicare and help pay for deductibles and coinsurance. Wisconsin has specific Medigap rules including guaranteed issue rights during certain times.

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.