Winona, MN Local Medicare Insurance Agents
Looking for Local Medicare agents in Winona, MN? Look no further than Medicare Agents Hub! Winona is a picturesque city nestled between the bluffs of the Mississippi River Valley, known for its natural beauty, abundance of outdoor activities, and rich history. Did you know that the first-ever ski tow was invented and installed in Winona in 1936? Today, Winona is a thriving community with several top-notch healthcare facilities and a number of experienced Medicare insurance professionals available to help you make the best decisions for your healthcare needs. Let us connect you with the best local Medicare agents in Winona!
Top 8 Medicare Agents & Brokers Serving Winona, MN
The following featured Medicare Experts are top rated in Winona and throughout Winona County, MN. These local representatives are our picks as the best Medicare agents in Winona, and are ready to help you navigate all of the most important parts of signing up for Medicare.
Refine Results Further by Zip Code
Looking for more specific results within Winona or Minnesota? Simply enter in your zip code for a full list of Medicare agents in your area.
Use our free online directory to find Medicare insurance agents in Winona zip code 55987.
MedicareAgentsHub.com also features licensed Medicare insurance brokers in nearby communities Goodview, St. Charles, Holmen, La Crescent, French Island, Onalaska, Plainview, La Crosse, West Salem, and Rochester.

Why work with a local Winona Medicare Expert?
Working with a local Medicare representative has many advantages over direct enrollment or working with a nation-wide agent.
- Familiar with Winona: Local agents take extra time to understand your personal situation and understand what everyday life is like in Winona County.
- Different Local Pricing: Medicare plan pricing can vary significantly by zip code. So the exact same plan in Winona might be a totally different price in Goodview or St. Charles. Local Medicare experts can provide accurate quotes and help you compare and choose a local Medicare plan in real time.
- Intimate Medicare Knowledge: Representatives familiar with Winona plans will be able to explain everything you need to know about Medicare, without having to spend countless hours doing your own research. If you wish to learn more about Medicare prior to meeting with your agent, be sure to check out our list of Winona Medicare & Senior Resources.






Latest Medicare Insights From Agents
Helpful information and articles from top rated agents across the country to help you learn about Medicare as you are browsing for a Winona Medicare agent.

Medicare in 2025: Must-Know Changes and Challenges for New and Current Enrollees
Written by Douglas Carney
In 2025, Medicare’s transformative changes are sparking discussions among new and current enrollees. From cost-saving measures to privatization concerns, these shifts are reshaping healthcare planning. Here are the top trending topics you need to know, based on recent updates.

Critical Medicare Mistakes to Avoid (and How to Protect Yourself)
Written by Robert Vaughan, R.Ph., MBA
Whether you are approaching eligibility or helping a loved one manage their transition into Medicare, it is essential to understand what not to do. Avoiding common mistakes can save you thousands of dollars in penalties, help you access the care you need when you need it, and give you peace of mind for the future.

The Best Way to Apply for Medicare with a Plan G Supplement
Written by Charise Karjala
This guide breaks down everything you need to know about Medigap Plan G—one of the most popular and comprehensive supplemental insurance options for retirees. You’ll learn why Plan G stands out, especially if you prefer private hospitals. Learn how to apply for Medicare with Plan G, what it covers (like Part B excess charges), and when to enroll to get the best rates.
Local Resources for Seniors in Winona
Discover essential services for seniors in Winona, Minnesota. In addition to connecting seniors with Medicare insurance agents & brokers in Winona, we've curated a selection of helpful links to local resources that provide information and community support for Winona seniors.
Minnesota Senior Linkage Line
Minnesota Senior Linkage Line is a comprehensive resource dedicated to providing seniors with vital information about healthcare choices, particularly regarding Medicare plans. With a focus on aiding older Minnesotans, it offers services such as 'Aging in Place' plans, assistance for caregivers, and unbiased help to select the most suitable Medicare plan for you.
Senior Community Services of Minnesota
Senior Community Services of Minnesota offers comprehensive support to Minneapolis seniors, promoting independence and community connection. Emphasizing inclusivity and diversity, they provide valuable services and resources to help older adults thrive as they age.