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Find Supplemental Insurance Agents Near You in Winchester, VA

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

The top-rated supplemental insurance agent in Winchester, Virginia is Blue Ridge Agents Insurance, rated 5.0 stars across 402 reviews. Other highly rated options include Creekside Insurance Advisors, Inc., Homestead Insurance Group, I Know Medicare. This directory lists 20 supplemental insurance agents serving Winchester.

Showing 20 supplemental 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
2Creekside Insurance Advisors, Inc.167 Creekside Ln(540) 722-2529
3Homestead Insurance Group3113 Valley Ave #100(844) 359-5731
4I Know Medicare28 Weems Ln(540) 662-4432
5Lynne Rio Insurance Agency226 S Loudoun St(540) 665-0086
6Walter & Walter Insurance Agency3186 Valley Pike(540) 662-1212
7TWG Insurance24 W Piccadilly St(540) 662-1828
8Mark Dunford Insurance Agency3223 Valley Pike(540) 665-0911
9Wilkins Insurance Agency, Inc.4125 Valley Pike(540) 667-6611
10HIS Insurance & Service, Inc.2810 Valley Ave(540) 535-0200
BR
141 W Boscawen St
Blue Ridge Agents Insurance
Supplemental Insurance Agent · Winchester, VA

Blue Ridge Agents Insurance serves the Winchester, Virginia, area as a supplemental insurance agent. The company helps clients explore additional coverage options that work alongside primary health or life policies. These plans can assist with out-of-pocket costs not covered by major medical plans. Supplemental insurance agents in this region often focus on policies for accident recovery, critical illness events, or hospital stays. Blue Ridge Agents Insurance handles such supplemental accident and specified disease policies in its local market.

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

Creekside Insurance Advisors, Inc. in Winchester, VA provides supplemental insurance solutions for individuals and businesses in the region. Their services include policy review, enrollment assistance, and ongoing claims support to help clients fill gaps in their primary coverage. They offer maintenance through scheduled consultations and annual policy reassessments. The company specializes in servicing a range of properties, including single-family homes, apartments, retail locations, and restaurants.

HI
3113 Valley Ave #100
Homestead Insurance Group
Supplemental Insurance Agent · Winchester, VA

Homestead Insurance Group serves homeowners, businesses, and property managers in Winchester, Virginia, who need supplemental insurance coverage. The agency helps clients fill gaps in their primary plans, offering policies such as accident, critical illness, and hospital indemnity insurance. These plans provide financial protection for unexpected medical costs and income loss. The agency focuses on explaining complex coverage options clearly so local residents and business owners can make informed decisions. Homestead Insurance Group also serves clients in the neighboring community of Berryville and across Frederick County.

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

I Know Medicare serves Winchester, Virginia, and the surrounding communities in the northern Shenandoah Valley. As a supplemental insurance agency, it helps clients navigate Medicare gap plans and additional coverage options to address out-of-pocket expenses. The company focuses on matching individuals with policies that suit their specific healthcare needs and budget considerations. For a typical job, it follows a consultative process of reviewing a client’s current coverage, comparing available plan choices, and explaining the differences in benefits and premiums.

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

Lynne Rio Insurance Agency, based in Winchester, VA, helps clients decide between one-time fixed-benefit plans and recurring coverage that renews periodically. Supplemental insurance fills gaps left by major medical policies, offering financial protection for unexpected events like accidents or critical illness. These policies provide cash benefits directly to the policyholder. Service operates on an as-needed basis, meaning clients can request new coverage or adjust existing plans whenever their personal circumstances or health needs change.

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

Walter & Walter Insurance Agency in Winchester, VA offers supplemental insurance policies that cover gaps left by major medical plans, including accident, critical illness, and hospital indemnity coverage. It also assists clients with Medicare supplement options and life insurance selections to ensure comprehensive financial protection. Seasonal concerns such as summer travel injuries or winter illnesses are periods when extra cash benefits from supplemental plans can help cover deductibles and out-of-pocket expenses.

TI
24 W Piccadilly St
TWG Insurance
Supplemental Insurance Agent · Winchester, VA

As the seasons change in the Winchester area, homeowners and families often find themselves re-evaluating their existing health coverage. TWG Insurance works as a supplemental insurance agent to help local residents identify gaps in their primary plans. The company can explain options for filling deductibles or covering costs that traditional policies may not address. A typical first step involves scheduling a brief inspection of one’s current coverage followed by a straightforward initial-assessment consultation to determine specific needs.

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

Mark Dunford Insurance Agency offers supplemental insurance solutions designed to fill coverage gaps left by primary health plans. Operating in Winchester, VA, the agency specializes in additional policies that help manage out-of-pocket expenses and unexpected medical costs. Clients can explore various add-on protections to strengthen their overall financial safety net. Commercial sectors it can serve include offices, warehouses, and food service establishments, providing tailored support for diverse business operations.

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

Wilkins Insurance Agency, Inc. serves residents of Winchester, VA with supplemental insurance policies designed to fill common gaps in primary health coverage. The agency also offers such plans for commercial clients in and around the city. Its agents explain policy options clearly, helping clients select plans that address specific financial risks from illness or injury. This straightforward service often results in ongoing relationships, with clients returning prior to each new enrollment period to review and adjust their current coverage.

HI
2810 Valley Ave
HIS Insurance & Service, Inc.
Supplemental Insurance Agent · Winchester, VA

HIS Insurance & Service, Inc. is a supplemental insurance agent in Winchester, VA, known for helping clients fill coverage gaps that traditional health plans may not address. Its service range includes policies for accident, critical illness, and hospital indemnity, designed to cover out-of-pocket expenses. These plans can help individuals manage financial risks from unforeseen medical events. A specialty service the agency can add on is short-term disability coverage to replace income during recovery.

CM
1000 Valley Ave #3
The Chad M. Lewis Insurance Agency
Supplemental Insurance Agent · Winchester, VA
(540) 313-9100
agency.nationwide.com/va/winchester/22601/chad-matthew-lewis
IC
728 S Loudoun St
Insurance Center of Winchester
Supplemental Insurance Agent · Winchester, VA
(540) 667-0700
inscenterwin.com
BL
704 Baker Ln Ste 1
Bankers Life
Supplemental Insurance Agent · Winchester, VA
(540) 662-2142
branches.bankerslife.com/va/winchester/704-baker-lane
PI
2333 N Frederick Pike
Partlow Insurance Agency, Inc.
Supplemental Insurance Agent · Winchester, VA
(540) 665-8387
partlowinsurance.com
JT
704 Baker Ln Ste 1
Jay Thompson, Bankers Life Agent
Supplemental Insurance Agent · Winchester, VA
(540) 662-2142
agents.bankerslife.com/va/winchester/704-baker-lane/jay-thompson
KC
704 Baker Ln Ste 1
Katherine Cockrell, Bankers Life Agent
Supplemental Insurance Agent · Winchester, VA
(540) 662-2142
agents.bankerslife.com/va/winchester/704-baker-lane/katherine-cockrell
SI
100 N Loudoun St Suite 130
Steinlage Insurance Agency of Winchester
Supplemental Insurance Agent · Winchester, VA
(636) 561-5060
steinlageagency.com
JE
704 Baker Ln Ste 1
John Evans, Bankers Life Agent
Supplemental Insurance Agent · Winchester, VA
(540) 662-2142
agents.bankerslife.com/va/winchester/704-baker-lane/john-evans
GM
704 Baker Ln Ste 1
Gena Maxwell, Bankers Life Agent
Supplemental Insurance Agent · Winchester, VA
(540) 662-2142
agents.bankerslife.com/va/winchester/704-baker-lane/gena-maxwell
PP
704 Baker Ln Ste 1
Pete Pendleton, Bankers Life Agent
Supplemental Insurance Agent · Winchester, VA
(540) 662-2142
agents.bankerslife.com/va/winchester/704-baker-lane/pete-pendleton

What Does a 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.

About supplemental insurance agents in Winchester

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.

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.

Supplemental Insurance Agents in Other Virginia Cities

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