Winona, MS Local Medicare Insurance Agents
At Medicare Agents Hub in Winona, MS, you'll find a dedicated team of local Medicare agents ready to assist you in navigating your healthcare options. Our directory helps you connect with knowledgeable Medicare brokers and advisors who can provide personalized plans tailored to your needs. Did you know Winona is often referred to as the "Crossroads of North Mississippi"? This charming city sits at the intersection of U.S. Highways 51 and 82, making it a pivotal spot for connecting people—much like how our directory connects you with the best Medicare assistance in town.
Top 8 Medicare Agents & Brokers Serving Winona, MS
The following featured Medicare Experts are top rated in Winona and throughout Montgomery County, MS. 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 Mississippi? 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 38967.
MedicareAgentsHub.com also features licensed Medicare insurance brokers in nearby communities Grenada, Greenwood, Kosciusko, Itta Bena, Louisville, Water Valley, Belzoni, Houston, Starkville, and Carthage.
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 Montgomery 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 Grenada or Greenwood. 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.

Pay Now or Pay Later: The Real Cost of Medicare Advantage vs. Medigap
Written by Todd Bostic
Medicare Advantage plans may seem like a great deal with all their extras, but they often come with hidden costs when you actually need care. With Medigap, you pay more upfront each month, but you usually walk into a doctor or hospital and owe nothing.

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.
Local Resources for Seniors in Winona
Discover essential services for seniors in Winona, Mississippi. 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.
Finding Services for Older Adults in Mississippi
Discover a bounty of resources for older adults living in Mississippi with this in-depth guide. Optimized to aid seniors and their families in finding healthcare, nutritional assistance, transportation, and more, this tool is tailored to meet unique needs fitting individual circumstances.
Visit the Finding Services for Older Adults in Mississippi website »