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Compare medicare insurance agents in Winchester. Review contact information and insurance categorys before you decide.
19 agents listed
Updated May 2026
Winchester, VA
Important: Listings are compiled from publicly available sources and have not been independently verified by BeforeInsuranceUSA.com. We do not endorse any agent or guarantee outcomes. Verify licensing and disciplinary status with the Department of Insurance of Virginia before hiring.
Showing 19 medicare insurance agents in Winchester, VA
Listings are displayed in no particular order and are not ranked by BeforeInsuranceUSA. Order does not constitute a recommendation or endorsement of any agent.
Blue Ridge Agents Insurance
141 W Boscawen St, Winchester, VA 22601
(540) 431-4373
blueridgeagents.com
Ryan Meyer - State Farm Insurance Agent
625 Millwood Ave #1, Winchester, VA 22601
(540) 869-0644
ryanmeyerinsurance.com
Creekside Insurance Advisors, Inc.
167 Creekside Ln, Winchester, VA 22602
(540) 722-2529
creeksideadvisors.net
I Know Medicare
28 Weems Ln, Winchester, VA 22601
(540) 662-4432
medicaretrustedagents.com
Lynne Rio Insurance Agency
226 S Loudoun St, Winchester, VA 22601
(540) 665-0086
rio-insurance.com
Kim Smith - State Farm Insurance Agent
136 Weems Ln, Winchester, VA 22601
(540) 662-5453
kimsmithinsurance.com
Walter & Walter Insurance Agency
3186 Valley Pike, Winchester, VA 22602
(540) 662-1212
walterandwalter.com
Mark Dunford Insurance Agency
3223 Valley Pike, Winchester, VA 22602
(540) 665-0911
dunfordinsurance.com
Wilkins Insurance Agency, Inc.
4125 Valley Pike, Winchester, VA 22602
(540) 667-6611
wilkinsinsuranceinc.com
Strawderman Financial
2400 Valley Ave STE LL7, Winchester, VA 22601
(540) 336-8382
strawdermanfinancial.com
Virginia Farm Bureau Insurance Company
125 Prosperity Dr, Winchester, VA 22602
(540) 869-8650
vafb.com
Insurance Center of Winchester
728 S Loudoun St, Winchester, VA 22601
(540) 667-0700
inscenterwin.com
The Chad M. Lewis Insurance Agency
1000 Valley Ave #3, Winchester, VA 22601
(540) 313-9100
agency.nationwide.com
Pro Prime Insurance VA
163 Creekside Ln, Winchester, VA 22602
(540) 425-3102
Partlow Insurance Agency, Inc.
2333 N Frederick Pike, Winchester, VA 22603
(540) 665-8387
partlowinsurance.com
Bankers Life
704 Baker Ln Ste 1, Winchester, VA 22603
(540) 662-2142
branches.bankerslife.com
Miramontes Insurance LLC
124 Weems Ln, Winchester, VA 22601
(540) 877-7842
miramontesinsurance.com
Pro Prime Insurance VA
230 Hope Dr, Winchester, VA 22601
(540) 662-3040
Steinlage Insurance Agency of Winchester
100 N Loudoun St Suite 130, Winchester, VA 22601
(636) 561-5060
steinlageagency.com
Medicare insurance agents in Winchester Virginia help residents compare Medicare Advantage and Part D plans. Virginia law requires agents to be licensed and follow state disclosure rules. Local agents understand the Shenandoah Valley healthcare network options.
What Does a Medicare Insurance Agent in Winchester Cost?
Medicare insurance agents in Virginia do not charge you a fee for their services. They receive commissions from insurance companies. Plan costs vary by provider and coverage level. For example, Medicare Advantage plans may have $0 monthly premiums or up to $200 per month. Part D prescription plans range from $10 to $100 per month. This is general information and not insurance advice.
* Cost estimates are general ranges based on publicly available data and compiled using automated research tools. Actual fees vary by agent and case complexity. This is not insurance advice — consult directly with an agent for fee specifics.
Frequently Asked Questions
What does a Medicare insurance agent in Winchester do?
A Medicare insurance agent helps you compare plans and enroll in Medicare Advantage or Part D. They must be licensed by the Virginia Bureau of Insurance. They do not charge you directly as they are paid by insurance companies.
When can I enroll in Medicare in Winchester Virginia?
Your Initial Enrollment Period starts three months before you turn 65 and ends three months after. Virginia also follows the annual Open Enrollment Period from October 15 to December 7. Special Enrollment Periods are available for certain life events.
Are Medicare agents in Winchester required to follow Virginia laws?
Yes. Virginia Code Title 38.2 requires agents to be licensed and follow strict marketing guidelines. Agents must not use high-pressure sales tactics and must provide clear plan comparisons.
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About Our Listings
Agents listed on BeforeInsuranceUSA.com are compiled from publicly available directories, state department of insurance records, and business listings. Inclusion does not constitute endorsement. We do not verify agent licensing, disciplinary status, or qualifications. Verify each agent's current standing with the Department of Insurance of Virginia.