Sign up for Medicare in Winchester, VA
Local licensed agents in Winchester County are available to assist you if you need help comparing plans or registering for Medicare insurance.
Original Medicare
Original Medicare (Part A) covers most medically necessary services.
Medicare Supplement
Medigap plans provide additional insurance for out of pocket costs.
Medicare Advantage
A bundled alternative to Original Medicare for your health and drug coverage.
Not sure what Medicare plan is right for you?
Winchester, VA Medicare Supplement Insurance Plan Comparison
First, decide between Traditional Medicare (which covers Parts A and B) and a private insurance's Medicare Advantage (known as Part C). If you go with Traditional Medicare, you'll probably also need a Medigap insurance to cover extra costs and a Part D plan for prescription drugs.
Medicare Advantage Plans: Age 65, Zipcode 22601, Non-smoker*
| Plan Type | Number of Plans Available | Average Monthly Premium | Lowest Monthly Premium | Highest Monthly Premium | Carriers |
|---|---|---|---|---|---|
| $0 OOP Medicare Advantage Plans | 47 | $0.00 | $0.00 | $0.00 | Aetna Medicare, Humana, Wellcare |
| Paid Medicare Advantage Plans | 10 | $53.85 | $11.30 | $109.20 | Aetna Medicare, Humana, UnitedHealthcare |
*Plan data last updated on 1/15/2026
Most Popular Medigap Plans: Female, Age 65, Zipcode 22601, Non-smoker*
| Plan Type | Number of Plans Available | Average Monthly Premium | Lowest Monthly Premium | Highest Monthly Premium | Carriers |
|---|---|---|---|---|---|
| Plan F | 27 | $184.88 | $124.86 | $292.23 | Physicians Select, Ace Property and Casualty, Insurance Company of North America, and 24 others |
| Plan G | 27 | $144.70 | $102.47 | $212.00 | Physicians Select, Ace Property and Casualty, Insurance Company of North America, and 24 others |
| Plan N | 26 | $108.35 | $76.13 | $175.64 | Ace Property and Casualty, Insurance Company of North America, State Farm, and 23 others |
*Plan data last updated on 1/15/2026
Most Popular Medigap Plans: Male, Age 65, Zipcode 22601, Non-smoker*
| Plan Type | Number of Plans Available | Average Monthly Premium | Lowest Monthly Premium | Highest Monthly Premium | Carriers |
|---|---|---|---|---|---|
| Plan F | 27 | $206.45 | $143.58 | $336.06 | Physicians Select, Ace Property and Casualty, Insurance Company of North America, and 24 others |
| Plan G | 27 | $161.01 | $117.85 | $241.24 | Physicians Select, Ace Property and Casualty, Insurance Company of North America, and 24 others |
| Plan N | 26 | $120.63 | $87.55 | $196.72 | Ace Property and Casualty, Insurance Company of North America, State Farm, and 23 others |
*Plan data last updated on 1/15/2026
Disclaimer: The information provided in these tables is for general informational purposes only. We make no guarantees about the accuracy, completeness, or reliability of the data. Please consult with a professional advisor or insurance provider for precise and up-to-date information.
Need help? Speak to a licensed Medicare insurance agent in Winchester today

Phillip Davis
Licensed Medicare Agent
Contact Phillip through Medicare Agents Hub »
Winchester, VA Medicare Resource Center
Winchester Medicare Information
Are you turning 65 or looking to change your Medicare plan in Winchester, VA? MedicareSignups.com has got you covered with our easy-to-use plan comparison tool. Plus, did you know that Winchester was the hometown of country music legend Patsy Cline? Take a stroll through Old Town Winchester and visit the Patsy Cline Historic House for a dose of music history. Enrolling in Medicare has never been easier, so sign up today to ensure you have the best coverage for your healthcare needs in Winchester.
Enroll in a Winchester Virginia Medicare Plan. Compare Plans »
Winchester, VA Local Medicare Offices
Virginia Official State Health Insurance Assistant Program
Virginia's official state SHIP program is the VA Insurance Counseling & Assistance Program (VICAP).





