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Find Supplemental Insurance Agents in Winchester, VA

Browse supplemental insurance agents serving Winchester, Virginia. Contact information and addresses listed below.

20 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 20 supplemental 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
Creekside Insurance Advisors, Inc.
167 Creekside Ln, Winchester, VA 22602
(540) 722-2529 creeksideadvisors.net
Homestead Insurance Group
3113 Valley Ave #100, Winchester, VA 22601
(844) 359-5731 homesteadinsurancegroup.com
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
Walter & Walter Insurance Agency
3186 Valley Pike, Winchester, VA 22602
(540) 662-1212 walterandwalter.com
TWG Insurance
24 W Piccadilly St, Winchester, VA 22601
(540) 662-1828 twg-insurance.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
HIS Insurance & Service, Inc.
2810 Valley Ave, Winchester, VA 22601
(540) 535-0200 his-insurance.com
The Chad M. Lewis Insurance Agency
1000 Valley Ave #3, Winchester, VA 22601
(540) 313-9100 agency.nationwide.com
Insurance Center of Winchester
728 S Loudoun St, Winchester, VA 22601
(540) 667-0700 inscenterwin.com
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
Jay Thompson, Bankers Life Agent
704 Baker Ln Ste 1, Winchester, VA 22603
(540) 662-2142 agents.bankerslife.com
Katherine Cockrell, Bankers Life Agent
704 Baker Ln Ste 1, Winchester, VA 22603
(540) 662-2142 agents.bankerslife.com
Steinlage Insurance Agency of Winchester
100 N Loudoun St Suite 130, Winchester, VA 22601
(636) 561-5060 steinlageagency.com
John Evans, Bankers Life Agent
704 Baker Ln Ste 1, Winchester, VA 22603
(540) 662-2142 agents.bankerslife.com
Gena Maxwell, Bankers Life Agent
704 Baker Ln Ste 1, Winchester, VA 22603
(540) 662-2142 agents.bankerslife.com
Pete Pendleton, Bankers Life Agent
704 Baker Ln Ste 1, Winchester, VA 22603
(540) 662-2142 agents.bankerslife.com

Supplemental insurance agents in Winchester, Virginia help residents find policies that cover gaps in Medicare or employer health plans. Virginia law requires agents to be licensed by the State Corporation Commission. Local agents understand the needs of the Winchester community and can explain options like Medigap and cancer insurance.

What Does a Supplemental Insurance Agent in Winchester Cost?

Costs for supplemental insurance in Virginia vary by plan type, age, and health status. Medigap Plan G premiums in Winchester typically range from $120 to $250 per month. Medicare Advantage plans may have low or zero premiums but include copays. 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 is the difference between Medigap and Medicare Advantage in Virginia?
Medigap supplements Original Medicare and pays for some out-of-pocket costs. Medicare Advantage plans replace Original Medicare and often include drug coverage. Virginia allows both options, but each has different rules for enrollment and network restrictions.
When can I enroll in a supplemental insurance plan in Winchester?
The initial enrollment period for Medigap starts when you turn 65 and enroll in Medicare Part B. In Virginia, you have a six-month open enrollment window. Outside this time, you may face medical underwriting.
Do Virginia agents have to follow special rules for selling supplemental insurance?
Yes, Virginia agents must comply with the Virginia Insurance Code and cannot engage in high-pressure sales. They must clearly explain plan benefits and limitations. The Virginia Bureau of Insurance oversees agent conduct.