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HomeMedicare Insurance AgentsVirginia › Chesapeake

Find Medicare Insurance Agents Near You in Chesapeake, VA

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

The top-rated medicare insurance agent in Chesapeake, Virginia is Michelle Benson-Dumas - State Farm Insurance Agent, rated 5.0 stars across 266 reviews. Other highly rated options include Centerville Insurance Agency, Shawn Fischer - State Farm Insurance Agent, Ferguson Insurance Center. This directory lists 19 medicare insurance agents serving Chesapeake.

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

Comparison

Top 10 listings
#NameAddressPhone
1Michelle Benson-Dumas - State Farm Insurance Agent1428 Kempsville Rd ste b(757) 819-6733
2Centerville Insurance Agency516 Innovation Dr Ste 301(757) 420-0006
3Shawn Fischer - State Farm Insurance Agent825 S Battlefield Blvd Ste B(757) 482-8350
4Ferguson Insurance Center1407 Stephanie Way Ste A(757) 201-3000
5Kathy Kretz - State Farm Insurance Agent838 Old George Washington Hwy N H(757) 487-0074
6Garlow Insurance Agency - Nationwide Insurance312 Cedar Lakes Dr suite 201(757) 548-1515
7Stephanie Grayson - State Farm Insurance Agent1111 Eden Way N(757) 547-9323
8COVA Insurance638 Independence Pkwy Ste 220(757) 410-5800
9Daryl Hines - State Farm Insurance Agent4448 Portsmouth Blvd # 100(757) 465-8000
10Nationwide Insurance: W T Jennings Insurance Agency Inc.676 Battlefield Blvd N Ste A(757) 549-2447
MB
1428 Kempsville Rd ste b
Michelle Benson-Dumas - State Farm Insurance Agent
Medicare Insurance Agent · Chesapeake, VA

Michelle Benson-Dumas - State Farm Insurance Agent serves clients in Chesapeake, VA, offering guidance on Medicare insurance plans. As a local agent, her work helps individuals navigate coverage options during their initial enrollment or annual open enrollment periods. She addresses questions regarding plan benefits, prescription drug coverage, and out-of-pocket costs. The agency handles both Medicare Supplement and Medicare Advantage plan selections for residents navigating their healthcare choices in this region.

CI
516 Innovation Dr Ste 301
Centerville Insurance Agency
Medicare Insurance Agent · Chesapeake, VA

Centerville Insurance Agency provides Medicare insurance guidance and enrollment assistance to clients in Chesapeake, Virginia. It helps individuals understand their options for medical coverage and prescription drug plans. The agency further offers ongoing support with plan reviews during the Annual Enrollment Period and Special Enrollment Periods, ensuring beneficiaries maintain appropriate coverage. Centerville Insurance Agency serves individual homeowners, residents of apartment complexes, and people living in retirement communities throughout the Chesapeake area.

SF
825 S Battlefield Blvd Ste B
Shawn Fischer - State Farm Insurance Agent
Medicare Insurance Agent · Chesapeake, VA

Shawn Fischer - State Farm Insurance Agent in Chesapeake, VA offers Medicare insurance guidance, helping clients understand plan options and enroll in coverage that aligns with their healthcare needs. The agency also provides related insurance services to support the local community. In addition to standard enrollment periods, the team assists with special enrollment situations such as relocating or losing existing coverage, ensuring timely access to necessary benefits.

FI
1407 Stephanie Way Ste A
Ferguson Insurance Center
Medicare Insurance Agent · Chesapeake, VA

Ferguson Insurance Center serves homeowners, retirees, and individuals in Chesapeake, Virginia, who are navigating their Medicare options. The agency offers guidance on Medicare Advantage, Supplement, and Part D drug plans, helping clients compare coverage to fit their healthcare needs and budget. Their licensed agents provide annual enrollment support and ongoing plan reviews to ensure beneficiaries have appropriate protection for changing health circumstances. The agency also serves clients in the neighboring Suffolk metropolitan area.

KK
838 Old George Washington Hwy N H
Kathy Kretz - State Farm Insurance Agent
Medicare Insurance Agent · Chesapeake, VA

Kathy Kretz - State Farm Insurance Agent, located in Chesapeake, VA, helps clients understand the difference between one-time enrollment events, such as the Initial Coverage Election Period, and recurring annual opportunities to adjust coverage like the Medicare Open Enrollment Period. Their focus includes explaining the distinctions between Medicare Supplement and Medicare Advantage plans. Service typically runs on an as-needed or scheduled basis, with no recurring automatic appointments unless a client requests a specific plan review each calendar year.

GI
312 Cedar Lakes Dr suite 201
Garlow Insurance Agency - Nationwide Insurance
Medicare Insurance Agent · Chesapeake, VA

Serving Chesapeake, VA, and the surrounding Hampton Roads communities, Garlow Insurance Agency - Nationwide Insurance handles Medicare insurance options for local residents. The agency assists clients with navigating Medicare plans, including supplement and advantage policies, to match individual healthcare needs and budgets. For a typical client, it begins by evaluating current coverage and personal health requirements before presenting a clear comparison of available local plan choices, ensuring each recommendation aligns with the client's specific situation.

SG
1111 Eden Way N
Stephanie Grayson - State Farm Insurance Agent
Medicare Insurance Agent · Chesapeake, VA

As Medicare enrollment periods approach each year, residents of Chesapeake, VA often seek clear guidance on their coverage options. Stephanie Grayson - State Farm Insurance Agent assists local seniors by explaining differences between original Medicare, Supplement plans, and Part D drug plans. The agency helps clients navigate plan comparisons during both the Annual Enrollment Period and special enrollment windows. An initial assessment can be scheduled to review individual health needs and prescription coverage requirements before making any plan selections.

CI
638 Independence Pkwy Ste 220
COVA Insurance
Medicare Insurance Agent · Chesapeake, VA

COVA Insurance provides guidance to Medicare beneficiaries in Chesapeake, VA. The company assists individuals with navigating original Medicare, supplement plans, and prescription drug coverage options. Their Medicare insurance agent services focus on coordinating enrollment periods and comparing available plans within the region. Customized advice is offered to help clients understand how to apply for and use their Medicare benefits correctly. COVA Insurance can serve commercial sectors such as professional offices, warehouses, and food service establishments with group or individual broker support.

DH
4448 Portsmouth Blvd # 100
Daryl Hines - State Farm Insurance Agent
Medicare Insurance Agent · Chesapeake, VA

Daryl Hines - State Farm Insurance Agent in Chesapeake, VA, is known for providing Medicare insurance guidance to local residents. The agency helps clients understand their coverage options during open enrollment periods and plan changes. It assists with comparing drug plans, preventive services, and out-of-pocket costs. Medicare supplement and Advantage plan differences are explained in clear terms. Specialty service includes assisting clients with enrollment forms for Medicare Part D prescription drug coverage, ensuring details are correctly submitted on time.

NI
676 Battlefield Blvd N Ste A
Nationwide Insurance: W T Jennings Insurance Agency Inc.
Medicare Insurance Agent · Chesapeake, VA

Residential clients in Chesapeake can access Medicare insurance plans through Nationwide Insurance: W T Jennings Insurance Agency Inc., which also offers commercial coverage options for local businesses. Serving the Chesapeake area and surrounding communities, the agency helps individuals navigate plan choices for medical and prescription drug coverage. A licensed agent can review current needs and compare available options during an annual enrollment visit, with follow-up support provided between those yearly appointments to adjust coverage as circumstances change.

MG
1021 Eden Way N # 104
McBride Group Inc.
Medicare Insurance Agent · Chesapeake, VA
(757) 410-9955
CF
616 Happy Acres Rd
Coastal Financial Insurance Group
Medicare Insurance Agent · Chesapeake, VA
(757) 350-6960
KW
103 Watson Rd
Kursti Woolard Medicare Insurance Broker, Life & Annuity Agent
Medicare Insurance Agent · Chesapeake, VA
(757) 692-8438
kurstiwoolardinsurance.com
PR
1015 Eden Way N suite c
Parker Reigle Insurance Agency
Medicare Insurance Agent · Chesapeake, VA
(757) 547-5118
parkerreigleinsurance.com
AA
524 Albemarle Dr Suite 207
Albearlie Affordable Insurance Agency - Chesapeake VA
Medicare Insurance Agent · Chesapeake, VA
(757) 520-3664
affordableautosecure.com/albearlie-affordable-insurance-agency-chesapeake-va
DW
7033 BOX
Deborah Williams Insurance Agency, Inc./Global Green Insurance Agency
Medicare Insurance Agent · Chesapeake, VA
(757) 967-9600
deborahwilliamsinsuranceagency.com
BL
860 Greenbrier Cir Ste 620
Bankers Life
Medicare Insurance Agent · Chesapeake, VA
(757) 549-5600
branches.bankerslife.com/va/chesapeake/860-greenbrier-circle
CI
1105 Madison Plaza #100
Chesapeake Insurance Services
Medicare Insurance Agent · Chesapeake, VA
(757) 436-4366
chesapeakeinsservices.com
HH
4310 Indian River Rd Ste 1A
HealthMarkets Health Insurance - Akiya Clark
Medicare Insurance Agent · Chesapeake, VA
(757) 979-7449
healthmarkets.com/akiya.clark

What Does a 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.

About medicare insurance agents in Chesapeake

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.

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.

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.