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.

Chris Schopmeyer - Medicare Agent serving Winona, MS
Chris Schopmeyer

#2 Top Rated Winona Broker

601-572-2220
Contact Chris
Tammy Burns - Medicare Agent serving Winona, MS
Tammy Burns

#3 Top Rated Winona Broker

662-238-4924
Contact Tammy
Holt Rushing - Medicare Agent serving Winona, MS
Holt Rushing

#4 Top Rated Winona Broker

662-257-8449
Contact Holt
John Henley - Medicare Agent serving Winona, MS
John Henley

#5 Top Rated Winona Broker

901-609-2156
Contact John
Sandra Bailey - Medicare Agent serving Winona, MS
Sandra Bailey

#6 Top Rated Winona Broker

901-831-0965
Contact Sandra
Brandon Wahl - Medicare Agent serving Winona, MS
Brandon Wahl

#7 Top Rated Winona Broker

601-844-3768
Contact Brandon
Tyler Coleman - Medicare Agent serving Winona, MS
Tyler Coleman

#8 Top Rated Winona Broker

205-690-1427
Contact Tyler

Local Winona Medicare Insurance Representatives by Distance

Maurice Ellis Medicare Agent Greenwood, MS 38930
Maurice Ellis

  • Greenwood, MS 38930 (27 mi.)
Jackson Taylor Medicare Agent Nettleton, MS 38858
Jackson Taylor

  • Nettleton, MS 38858 (77 mi.)
Jerry Hemphill Medicare Agent Louisville, MS 39339
Jerry Hemphill

WoodmenLife

  • Louisville, MS 39339 (47 mi.)
Andrea McMichael Medicare Agent Houston, MS 38851
Andrea McMichael

  • Houston, MS 38851 (50 mi.)
Lori Marion` Medicare Agent Houston, MS 38851
Lori Marion`

  • Houston, MS 38851 (50 mi.)
Reggie Rhodes Medicare Agent Yazoo City, MS 39194
Reggie Rhodes

  • Yazoo City, MS 39194 (58 mi.)
Jennifer Peters Medicare Agent Cleveland, MS 38732
Jennifer Peters

  • Cleveland, MS 38732 (60 mi.)
Romi Jaiswal Medicare Agent Oxford, MS 38655
Romi Jaiswal

  • Oxford, MS 38655 (61 mi.)
Debora Culver Medicare Agent Canton, MS 39046
Debora Culver

  • Canton, MS 39046 (63 mi.)
Justin Stark Medicare Agent Pontotoc, MS 38863
Justin Stark

Pontotoc Insurance Agency

  • Pontotoc, MS 38863 (67 mi.)
Jared Sparks Medicare Agent Pontotoc, MS 38863
Jared Sparks

  • Pontotoc, MS 38863 (67 mi.)
Will Chapman Medicare Agent Pontotoc, MS 38863
Will Chapman

  • Pontotoc, MS 38863 (67 mi.)
Shelby Rogers Medicare Agent Bentonia, MS 39040
Shelby Rogers

  • Bentonia, MS 39040 (70 mi.)
Shelia Spann Medicare Agent Madison, MS 39110
Shelia Spann

  • Madison, MS 39110 (75 mi.)
Craig Walker Medicare Agent Madison, MS 39110
Craig Walker

CWG Financial

  • Madison, MS 39110 (75 mi.)
Stacey Gaines Medicare Agent Madison, MS 39110
Stacey Gaines

  • Madison, MS 39110 (75 mi.)

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.
Insurance Agents Offering Aetna Medicare Plans in Winona, MS
Insurance Agents Offering Anthem Medicare Plans in Winona, MS
Insurance Agents Offering Humana Medicare Plans in Winona, MS
Insurance Agents Offering UnitedHealthcare Medicare Plans in Winona, MS
Insurance Agents Offering Cigna Medicare Plans in Winona, MS
Insurance Agents Offering Mutual Medicare Plans in Winona, MS

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 Insurance 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 Medicare Insurance 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 Medicare Insurance Agent
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 »