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Find Medicare Insurance Agents in Chesapeake, VA

Compare medicare insurance agents in Chesapeake. Review contact information and insurance categorys before you decide.

19 agents listed
Updated May 2026
Chesapeake, 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 Chesapeake, 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.
Michelle Benson-Dumas - State Farm Insurance Agent
1428 Kempsville Rd ste b, Chesapeake, VA 23320
(757) 819-6733 michellebensoninsurance.com
Centerville Insurance Agency
516 Innovation Dr Ste 301, Chesapeake, VA 23320
(757) 420-0006 centervilleinsure.com
Ferguson Insurance Center
1407 Stephanie Way Ste A, Chesapeake, VA 23320
(757) 201-3000 fergusonins.com
Garlow Insurance Agency - Nationwide Insurance
312 Cedar Lakes Dr suite 201, Chesapeake, VA 23322
(757) 548-1515 dongarlowins.com
Kathy Kretz - State Farm Insurance Agent
838 Old George Washington Hwy N H, Chesapeake, VA 23323
(757) 487-0074 kathykretz.com
Shawn Fischer - State Farm Insurance Agent
825 S Battlefield Blvd Ste B, Chesapeake, VA 23322
(757) 482-8350 shawnfischer.com
Stephanie Grayson - State Farm Insurance Agent
1111 Eden Way N, Chesapeake, VA 23320
(757) 547-9323 stephaniegrayson.com
COVA Insurance
638 Independence Pkwy Ste 220, Chesapeake, VA 23320
(757) 410-5800 covains.com
Nationwide Insurance: W T Jennings Insurance Agency Inc.
676 Battlefield Blvd N Ste A, Chesapeake, VA 23320
(757) 549-2447 jennings-insurance.com
Daryl Hines - State Farm Insurance Agent
4448 Portsmouth Blvd # 100, Chesapeake, VA 23321
(757) 465-8000 darylhines.com
McBride Group Inc.
1021 Eden Way N # 104, Chesapeake, VA 23320
(757) 410-9955
Coastal Financial Insurance Group
616 Happy Acres Rd, Chesapeake, VA 23323
(757) 350-6960
Kursti Woolard Medicare Insurance Broker, Life & Annuity Agent
103 Watson Rd, Chesapeake, VA 23320
(757) 692-8438 kurstiwoolardinsurance.com
Parker Reigle Insurance Agency
1015 Eden Way N suite c, Chesapeake, VA 23320
(757) 547-5118 parkerreigleinsurance.com
Chesapeake Insurance Services
1105 Madison Plaza #100, Chesapeake, VA 23320
(757) 436-4366 chesapeakeinsservices.com
Bankers Life
860 Greenbrier Cir Ste 620, Chesapeake, VA 23320
(757) 549-5600 branches.bankerslife.com
Albearlie Affordable Insurance Agency - Chesapeake VA
524 Albemarle Dr Suite 207, Chesapeake, VA 23322
(757) 520-3664 affordableautosecure.com
Deborah Williams Insurance Agency, Inc./Global Green Insurance Agency
7033 BOX, Chesapeake, VA 23323
(757) 967-9600 deborahwilliamsinsuranceagency.com
HealthMarkets Health Insurance - Akiya Clark
4310 Indian River Rd Ste 1A, Chesapeake, VA 23325
(757) 979-7449 healthmarkets.com

A Medicare insurance agent in Chesapeake Virginia can help you navigate Original Medicare Medicare Advantage and Part D drug plans. Virginia law requires agents to be licensed by the State Corporation Commission and to follow strict marketing guidelines during the Annual Enrollment Period from October 15 to December 7. Working with a local agent gives you access to plan options specific to the Hampton Roads area including providers like Sentara and Chesapeake Regional Medical Center.

What Does a Medicare Insurance Agent in Chesapeake Cost?

Medicare insurance agents in Virginia typically do not charge clients directly for their services. They receive commissions from the insurance companies whose plans they sell. The cost of a Medicare plan itself varies widely with Part B premiums starting around $174.70 per month in 2024 and Medicare Advantage plans often having $0 monthly premiums but varying copays and deductibles. 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 Chesapeake do?
A Medicare insurance agent helps you compare plans explain coverage options and assist with enrollment. They can review your current health needs and budget to find a suitable plan from multiple carriers. Agents in Virginia must be certified by the plans they sell and cannot charge you a fee for their services.
When can I enroll in Medicare in Chesapeake Virginia?
Your Initial Enrollment Period starts three months before you turn 65 and ends three months after your birthday month. The Annual Enrollment Period runs from October 15 to December 7 each year. Virginia also has a Special Enrollment Period for certain life events like moving or losing employer coverage.
Are there Virginia-specific rules for Medicare agents?
Yes Virginia agents must follow state regulations including a 24 hour cooling off period for certain plan enrollments. They cannot use high pressure sales tactics or make unsolicited door to door visits. Agents must also clearly disclose their license number and the plans they represent.