ADVERTISING DISCLOSURE: BeforeInsuranceUSA.com is an informational directory, not an insurance agency, broker, or licensed producer. We do not sell insurance or provide insurance advice. No agent-client relationship is created by using this site. Except where a listing is clearly marked Featured, no agent listed on this site has paid for their listing. Featured listings are paid advertisements. This is an advertisement.
HomeMedicare Insurance AgentsVirginia › Winchester

Find Medicare Insurance Agents Near You in Winchester, VA

Browse medicare insurance agents serving Winchester, Virginia. Updated 2026-07-14.

The top-rated medicare insurance agent in Winchester, Virginia is Blue Ridge Agents Insurance, rated 5.0 stars across 401 reviews. Other highly rated options include Ryan Meyer - State Farm Insurance Agent, Creekside Insurance Advisors, Inc., I Know Medicare. This directory lists 19 medicare insurance agents serving Winchester.

Showing 19 medicare insurance agents in Winchester, VAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Blue Ridge Agents Insurance141 W Boscawen St(540) 431-4373
2Ryan Meyer - State Farm Insurance Agent625 Millwood Ave #1(540) 869-0644
3Creekside Insurance Advisors, Inc.167 Creekside Ln(540) 722-2529
4I Know Medicare28 Weems Ln(540) 662-4432
5Lynne Rio Insurance Agency226 S Loudoun St(540) 665-0086
6Kim Smith - State Farm Insurance Agent136 Weems Ln(540) 662-5453
7Walter & Walter Insurance Agency3186 Valley Pike(540) 662-1212
8Mark Dunford Insurance Agency3223 Valley Pike(540) 665-0911
9Wilkins Insurance Agency, Inc.4125 Valley Pike(540) 667-6611
10Strawderman Financial2400 Valley Ave STE LL7(540) 336-8382
BR
141 W Boscawen St
Blue Ridge Agents Insurance
Medicare Insurance Agent · Winchester, VA

Blue Ridge Agents Insurance serves the Winchester, Virginia area as a Medicare insurance agent. The company helps clients navigate Medicare plans, including Medicare Advantage and Medicare Supplement options. It works with individuals approaching eligibility and those reviewing their annual coverage. These services include explaining enrollment periods and comparing plan benefits from various carriers. The agency specifically handles Part D prescription drug plan coordination and initial enrollment guidance for new Medicare beneficiaries.

RM
625 Millwood Ave #1
Ryan Meyer - State Farm Insurance Agent
Medicare Insurance Agent · Winchester, VA

Ryan Meyer as a State Farm Insurance agent in Winchester, VA offers a range of services focused on helping clients understand and select Medicare insurance plans. This includes guiding individuals through the complexities of enrollment periods and plan options to find coverage that fits their healthcare needs and budget. The agent provides ongoing support for plan maintenance, including annual reviews of coverage changes and assistance with claims questions. These services are available to individuals residing in single-family homes, apartments, and for those residing in retirement communities or similar multi-unit properties.

CI
167 Creekside Ln
Creekside Insurance Advisors, Inc.
Medicare Insurance Agent · Winchester, VA

Creekside Insurance Advisors, Inc. serves Medicare-eligible individuals and their families in the Winchester, Virginia area. The company assists clients in understanding their Medicare insurance options, including plan comparisons and enrollment guidance for supplemental coverage. They help beneficiaries navigate the annual enrollment period and find plans that fit their healthcare needs and budget. In addition to the Winchester community, Creekside Insurance Advisors extends its Medicare insurance agent services to residents of nearby Stephens City.

IK
28 Weems Ln
I Know Medicare
Medicare Insurance Agent · Winchester, VA

Serving Winchester, Virginia, and the surrounding Shenandoah Valley communities, I Know Medicare helps clients navigate Medicare health insurance options for their specific situations. The agency handles both initial enrollment and annual plan reviews. By taking time to understand each client’s healthcare needs and budget, it offers clear explanations of available plans. For a typical job, the agent compares multiple carriers’ coverage details to identify suitable choices for the individual.

LR
226 S Loudoun St
Lynne Rio Insurance Agency
Medicare Insurance Agent · Winchester, VA

Navigating Medicare can involve comparing initial enrollment options against ongoing plan adjustments. Lynne Rio Insurance Agency in Winchester, VA provides guidance for both one-time decisions and recurring coverage reviews, helping clients understand how Parts A, B, C, and D work together. The process includes evaluating plan costs, provider networks, and prescription formularies to find a suitable fit for individual healthcare needs. This service is available on an as-needed basis, allowing clients to schedule appointments only when a change in their health or plan benefits requires a fresh evaluation.

KS
136 Weems Ln
Kim Smith - State Farm Insurance Agent
Medicare Insurance Agent · Winchester, VA

As a Medicare insurance agent in Winchester, VA, this agency provides guidance on Medicare Advantage and Medicare Supplement plans, helping individuals navigate their coverage options. It also assists with general insurance services, addressing both health and life insurance needs to protect clients and their families. Seniors transitioning from employer coverage or turning sixty-five can receive personalized advice during the annual enrollment period, ensuring they understand deadlines and potential changes to existing policies.

WW
3186 Valley Pike
Walter & Walter Insurance Agency
Medicare Insurance Agent · Winchester, VA

As the annual Medicare open enrollment period approaches each fall, residents of Winchester, Virginia often seek clarity on their coverage options. Walter & Walter Insurance Agency provides guidance to local clients navigating Medicare Part A, Part B, and Part D plans. The company assists with comparing available plans in the region to find suitable coverage. An initial consultation is conducted to review a client's current health needs and enrollment period status.

MD
3223 Valley Pike
Mark Dunford Insurance Agency
Medicare Insurance Agent · Winchester, VA

Mark Dunford Insurance Agency works with clients across Winchester, VA to navigate Medicare options. This firm specializes in Medicare insurance agent services, helping individuals evaluate plan choices such as Medicare Advantage and Medigap. Agents assist with annual enrollment periods and plan comparisons to address personal healthcare needs. The agency’s client base commonly includes local office professionals, staff at regional warehouses, and workers in the food service sector seeking appropriate coverage guidance.

WI
4125 Valley Pike
Wilkins Insurance Agency, Inc.
Medicare Insurance Agent · Winchester, VA

Wilkins Insurance Agency, Inc. serves residential clients in Winchester, VA, helping them navigate Medicare coverage choices. The agency also assists with commercial insurance needs for local businesses. Its service area includes Winchester and the surrounding Shenandoah Valley communities. The team explains plan options during initial consultations and is available for follow-up questions or policy adjustments between regular annual enrollment visits.

SF
2400 Valley Ave STE LL7
Strawderman Financial
Medicare Insurance Agent · Winchester, VA

Strawderman Financial is a Medicare insurance agent based in Winchester, VA, known for guiding residents through their initial enrollment and annual plan options. It helps clients compare Medicare Advantage, Part D prescription drug plans, and Medicare Supplements. The agency assists individuals in understanding coverage gaps, out-of-pocket costs, and provider networks so they can select a plan suited to their health needs and budget. Among its available services, Strawderman Financial also provides guidance on selecting dental or vision add-on coverage.

CM
1000 Valley Ave #3
The Chad M. Lewis Insurance Agency
Medicare Insurance Agent · Winchester, VA
(540) 313-9100
agency.nationwide.com/va/winchester/22601/chad-matthew-lewis
VF
125 Prosperity Dr
Virginia Farm Bureau Insurance Company
Medicare Insurance Agent · Winchester, VA
(540) 869-8650
vafb.com/offices/winchester
PP
163 Creekside Ln
Pro Prime Insurance VA
Medicare Insurance Agent · Winchester, VA
(540) 425-3102
IC
728 S Loudoun St
Insurance Center of Winchester
Medicare Insurance Agent · Winchester, VA
(540) 667-0700
inscenterwin.com
MI
124 Weems Ln
Miramontes Insurance LLC
Medicare Insurance Agent · Winchester, VA
(540) 877-7842
miramontesinsurance.com
BL
704 Baker Ln Ste 1
Bankers Life
Medicare Insurance Agent · Winchester, VA
(540) 662-2142
branches.bankerslife.com/va/winchester/704-baker-lane
PI
2333 N Frederick Pike
Partlow Insurance Agency, Inc.
Medicare Insurance Agent · Winchester, VA
(540) 665-8387
partlowinsurance.com
PP
230 Hope Dr
Pro Prime Insurance VA
Medicare Insurance Agent · Winchester, VA
(540) 662-3040
SI
100 N Loudoun St Suite 130
Steinlage Insurance Agency of Winchester
Medicare Insurance Agent · Winchester, VA
(636) 561-5060
steinlageagency.com

What Does a 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.

About medicare insurance agents in Winchester

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.

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.

Medicare Insurance Agents in Other Virginia Cities

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each medicare insurance agent's credentials and current standing with your state Department of Insurance.