Winchester, KY Local Medicare Insurance Agents

Medicare Agents Hub is your go-to directory to find Local Medicare agents in Winchester, KY. Located in the heart of the Bluegrass Region, Winchester is known for its rich history as the birthplace of legendary frontiersman, Daniel Boone. But, this charming city is more than just history. Winchester boasts scenic beauty with a thriving downtown area, and it's a great place to retire. Having access to top-notch healthcare is essential, so make sure to utilize Medicare Agents Hub to connect with local experts who can help you navigate your Medicare options.

Top 8 Medicare Agents & Brokers Serving Winchester, KY

The following featured Medicare Experts are top rated in Winchester and throughout Clark County, KY. These local representatives are our picks as the best Medicare agents in Winchester, and are ready to help you navigate all of the most important parts of signing up for Medicare.

Claudia Bird - Medicare Agent serving Winchester, KY
Claudia Bird

#1 Top Rated Winchester Broker

859-298-7478
Contact Claudia
Allison Klein - Medicare Agent serving Winchester, KY
Allison Klein

#2 Top Rated Winchester Broker

513-442-2625
Contact Allison
Kim Ford - Medicare Agent serving Winchester, KY
Kim Ford

#3 Top Rated Winchester Broker

502-469-7238
Contact Kim
Jason Hark, CMIS™ - Medicare Agent serving Winchester, KY
Jason Hark, CMIS™

#4 Top Rated Winchester Broker

502-469-7605
Contact Jason
Michael Caldwell - Medicare Agent serving Winchester, KY
Michael Caldwell

#5 Top Rated Winchester Broker

812-214-9719
Contact Michael
Carrie Cordial - Medicare Agent serving Winchester, KY
Carrie Cordial

#7 Top Rated Winchester Broker

606-229-8571
Contact Carrie
Justin Lucas - Medicare Agent serving Winchester, KY
Justin Lucas

#8 Top Rated Winchester Broker

812-365-4561
Contact Justin

Local Winchester Medicare Insurance Representatives by Distance

Pete Alberti Medicare Agent Lexington, KY 40504
Pete Alberti

Kentucky Health Solutions

  • Lexington, KY 40504 (19 mi.)
Austin Tyler, MBA Medicare Agent Lexington, KY 40513
Austin Tyler, MBA

Tyler Insurance Group

  • Lexington, KY 40513 (23 mi.)
Rachel Lewis Medicare Agent Lexington, KY 40515
Rachel Lewis

Bluegrass Family Insurance Group LLC

  • Lexington, KY 40515 (12 mi.)
Travis Ellis Medicare Agent Paris, KY 40361
Travis Ellis

Medicare with Travis

  • Paris, KY 40361 (14 mi.)
Andre Dixon Medicare Agent Lexington, KY 40509
Andre Dixon

  • Lexington, KY 40509 (14 mi.)
Dave Martin Medicare Agent Lexington, KY 40509
Dave Martin

  • Lexington, KY 40509 (14 mi.)
David Chaims Medicare Agent Lexington, KY 40509
David Chaims

  • Lexington, KY 40509 (14 mi.)
Chris Ray Medicare Agent Lexington, KY 40509
Chris Ray

  • Lexington, KY 40509 (14 mi.)
Forrest Sevigny Medicare Agent Lexington, KY 40509
Forrest Sevigny

  • Lexington, KY 40509 (14 mi.)
Katie Ockerman Medicare Agent Lexington, KY 40509
Katie Ockerman

  • Lexington, KY 40509 (14 mi.)
Malissa Worrell Medicare Agent Lexington, KY 40509
Malissa Worrell

  • Lexington, KY 40509 (14 mi.)
Nick Hudson Medicare Agent Lexington, KY 40509
Nick Hudson

  • Lexington, KY 40509 (14 mi.)
Ryan Reed Medicare Agent Lexington, KY 40509
Ryan Reed

  • Lexington, KY 40509 (14 mi.)
Timothy Brown Medicare Agent Lexington, KY 40509
Timothy Brown

  • Lexington, KY 40509 (14 mi.)
Jonathon Murphy Medicare Agent Lexington, KY 40509
Jonathon Murphy

  • Lexington, KY 40509 (14 mi.)
Mary Howell Medicare Agent Lexington, KY 40509
Mary Howell

  • Lexington, KY 40509 (14 mi.)

Refine Results Further by Zip Code

Looking for more specific results within Winchester or Kentucky? 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 Winchester zip codes 40391 and 40392.

MedicareAgentsHub.com also features licensed Medicare insurance brokers in nearby communities Mount Sterling, Paris, Lexington, Richmond, Stanton, Nicholasville, Georgetown, Wilmore, Cynthiana, and Berea.

Why work with a local Winchester Medicare Expert?

Working with a local Medicare representative has many advantages over direct enrollment or working with a nation-wide agent.

  • Familiar with Winchester: Local agents take extra time to understand your personal situation and understand what everyday life is like in Clark County.
  • Different Local Pricing: Medicare plan pricing can vary significantly by zip code. So the exact same plan in Winchester might be a totally different price in Mount Sterling or Paris. 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 Winchester 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 Winchester Medicare & Senior Resources.
Insurance Agents Offering Aetna Medicare Plans in Winchester, KY
Insurance Agents Offering Anthem Medicare Plans in Winchester, KY
Insurance Agents Offering Humana Medicare Plans in Winchester, KY
Insurance Agents Offering UnitedHealthcare Medicare Plans in Winchester, KY
Insurance Agents Offering Cigna Medicare Plans in Winchester, KY
Insurance Agents Offering Mutual Medicare Plans in Winchester, KY

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 Winchester Medicare agent.

A Family Guide to Hospice and Medicare: What I Learned From My Mom’s Experience
Written by Michael Ferraro Medicare Insurance Agent
A Family Guide to Hospice and Medicare: What I Learned From My Mom’s Experience

Written by Michael Ferraro

I wasn’t prepared for what hospice meant until my mom needed it. This article shares what I learned about hospice care and how Medicare helps cover it, in hopes it can make things clearer for you and your family.

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.

Local Resources for Seniors in Winchester

Discover essential services for seniors in Winchester, Kentucky. In addition to connecting seniors with Medicare insurance agents & brokers in Winchester, we've curated a selection of helpful links to local resources that provide information and community support for Winchester seniors.

Kentucky Department for Aging and Independent Living

The Kentucky Department for Aging and Independent Living offers comprehensive services to elders and individuals with disabilities throughout Kentucky. Take advantage of their wealth of statewide resources tailored specifically for enhancing the lives of seniors and facilitating independent living.

Visit the Kentucky Department for Aging and Independent Living website »