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.

Find Supplemental Insurance Agents Near You in Annapolis, MD

Browse supplemental insurance agents serving Annapolis, Maryland. Updated 2026-07-14.

The top-rated supplemental insurance agent in Annapolis, Maryland is Mathes Insurance Advisors, Inc., rated 4.9 stars across 428 reviews. Other highly rated options include JSR Insurance, CNR Insurance Inc, Goosehead Insurance - Tim Coe. This directory lists 20 supplemental insurance agents serving Annapolis.

Showing 20 supplemental insurance agents in Annapolis, MDListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Mathes Insurance Advisors, Inc.2525 Riva Rd Suite 105(410) 295-9900
2JSR Insurance793 Fairview Ave(443) 529-9109
3CNR Insurance Inc166 West St(410) 897-9890
4Goosehead Insurance - Tim Coe1125 West St Suite 200, Office 244(443) 924-6704
5Sylvia Hopkins - GEICO Insurance Agent102 Old Solomons Island Rd Suite 301(410) 571-7722
6Old Bay Insurance Agency133 Defense Hwy #214(410) 777-5390
7East Coast Health Advisors619 Ridgely Ave #200(410) 896-1212
8Reyes Insurance LLC1831 Forest Dr # A(443) 440-0989
9Bay Area Insurance1 Annapolis St STE 100(410) 647-7333
10Henry M Murray Insurance Agency2498 Riva Rd(410) 224-2664
MI
2525 Riva Rd Suite 105
Mathes Insurance Advisors, Inc.
Supplemental Insurance Agent · Annapolis, MD

Mathes Insurance Advisors, Inc. serves the Annapolis metro area and Anne Arundel County as a local supplemental insurance agent. The agency helps individuals and families navigate coverage options that fill gaps left by major medical plans. These policies address everyday needs not fully covered by primary health insurance, providing financial protection for unexpected expenses. In this region, they specialize in hospital indemnity plans and accident insurance, which offer cash benefits for specific medical events.

JI
793 Fairview Ave
JSR Insurance
Supplemental Insurance Agent · Annapolis, MD

JSR Insurance provides supplemental insurance agent services in Annapolis, Maryland, helping clients fill gaps in their primary health coverage. The company offers new policy consultations and assistance with plan maintenance, including periodic policy reviews to ensure coverage remains aligned with needs. It regularly communicates with clients to update or adjust their supplemental benefits as circumstances change. JSR Insurance services properties such as single-family homes, apartments, retail locations, and restaurants.

CI
166 West St
CNR Insurance Inc
Supplemental Insurance Agent · Annapolis, MD

CNR Insurance Inc serves Annapolis, Maryland, and the surrounding communities, handling supplemental insurance needs such as Medicare supplements, gap coverage, and critical illness plans. The company helps clients fill the gaps in their primary health insurance by offering policies that cover out-of-pocket expenses like deductibles and copayments. To manage a typical job, the agency conducts a personal consultation to review the client’s existing coverage and then carefully presents policy options that match their specific budget and healthcare requirements.

GI
1125 West St Suite 200, Office 244
Goosehead Insurance - Tim Coe
Supplemental Insurance Agent · Annapolis, MD

Goosehead Insurance - Tim Coe serves Annapolis, Maryland, and the surrounding communities, handling supplemental insurance options that help cover gaps in primary health plans. The agency works with clients to identify policies for expenses like deductibles, copays, and critical illness costs. These plans are designed to complement existing coverage rather than replace it. To complete a typical job, the agent begins by reviewing a client’s current benefits and then presents clear, comparative options that align with the individual’s specific financial and health care needs.

SH
102 Old Solomons Island Rd Suite 301
Sylvia Hopkins - GEICO Insurance Agent
Supplemental Insurance Agent · Annapolis, MD

Sylvia Hopkins - GEICO Insurance Agent in Annapolis serves local homeowners, renters, and small business owners requiring supplemental insurance coverage. This agency helps clients fill gaps in their primary policies by offering tailored options such as accident or hospital indemnity plans. The team assists with understanding complex policy details and filing claims when needed. Its office extends its services to residents and businesses throughout neighboring communities in the Anne Arundel County metro area, including Severna Park and Edgewater.

OB
133 Defense Hwy #214
Old Bay Insurance Agency
Supplemental Insurance Agent · Annapolis, MD

Old Bay Insurance Agency in Annapolis, Maryland distinguishes between one-time supplemental policies and recurring coverage options designed for ongoing protection. Their focus includes filling gaps left by primary health or life insurance plans in the local area. For clients requiring occasional adjustments after a major life event, the agency typically schedules appointments on an as-needed basis rather than offering a fixed service calendar.

EC
619 Ridgely Ave #200
East Coast Health Advisors
Supplemental Insurance Agent · Annapolis, MD

East Coast Health Advisors in Annapolis, Maryland specializes in supplemental insurance policies that fill gaps in primary coverage, including plans for accident, critical illness, and hospital indemnity. The agency works with clients to evaluate existing benefits and select supplemental options that address specific financial risks. Many area residents turn to the firm for guidance during the Medicare open enrollment period when individuals may wish to review or adjust their supplemental coverage for the coming year.

RI
1831 Forest Dr # A
Reyes Insurance LLC
Supplemental Insurance Agent · Annapolis, MD

As residents of Annapolis prepare for winter's higher heating bills and seasonal illnesses, gaps in Medicare or other health coverage can become a pressing concern. Reyes Insurance LLC serves this local need by providing supplemental insurance plans that help cover costs such as copays and deductibles. The agency works with clients to review existing coverage and identify potential gaps. An initial assessment is conducted to evaluate individual insurance needs and policy options.

BA
1 Annapolis St STE 100
Bay Area Insurance
Supplemental Insurance Agent · Annapolis, MD

Bay Area Insurance provides supplemental insurance coverage to individuals and businesses throughout Annapolis, Maryland. The agency specializes in offering add-on policies that help fill gaps left by primary health, life, or disability plans. These plans can assist with out-of-pocket expenses and income protection during unexpected medical events. The agency serves a variety of commercial sectors, including offices, warehouses, and food service operations, tailoring coverage to meet the unique needs of each workplace environment.

HM
2498 Riva Rd
Henry M Murray Insurance Agency
Supplemental Insurance Agent · Annapolis, MD
SB
108 Old Solomons Island Rd Bldg 2
Simpson and Blom Insurance
Supplemental Insurance Agent · Annapolis, MD
(410) 573-9104
simpsonandblom.com
RS
2049 West St Suite 202
Ramsey's Insurance, Inc
Supplemental Insurance Agent · Annapolis, MD
(410) 266-9363
ramseys-insurance.com
JM
111 Forbes St
Jack Martin Insurance Advisors
Supplemental Insurance Agent · Annapolis, MD
(410) 263-8000
askjack.cc
FS
1997 Annapolis Exchange Ste 300
Full Sail Insurance
Supplemental Insurance Agent · Annapolis, MD
(410) 671-0928
fullsailinsurance.com
GI
1997 Annapolis Exchange Suite 410
Goosehead Insurance - Brian Madden
Supplemental Insurance Agent · Annapolis, MD
(301) 476-6012
goosehead.com/agents/md/annapolis/brian-madden
GI
888 Bestgate Rd Suite 104
Gallagher Insurance, Risk Management & Consulting
Supplemental Insurance Agent · Annapolis, MD
assuredpartners.com/annapolis
IM
170 Jennifer Rd
Insurance Management Associates, Inc.
Supplemental Insurance Agent · Annapolis, MD
(410) 873-9964
MP
133 Defense Hwy #214
Maryland Permanent Insurance
Supplemental Insurance Agent · Annapolis, MD
(410) 777-5390
oldbayinsurance.com
HI
170 Jennifer Rd Suite 205
HUB International
Supplemental Insurance Agent · Annapolis, MD
(410) 266-8888
hubinternational.com/offices/us/maryland/annapolis-jennifer-road
AI
60 West St Suite 61
Annapolis Insurance Advisors
Supplemental Insurance Agent · Annapolis, MD
(443) 600-7400
annapolisinsuranceadvisors.com

What Does a a Supplemental Insurance Agent in Annapolis Cost?

Medigap premiums in Maryland vary by plan type age and location. Monthly costs can range from about 100 dollars for Plan A to over 300 dollars for Plan F. Medicare Advantage plans often have low or zero premiums but include copays and deductibles. This information is general and not insurance advice.

About supplemental insurance agents in Annapolis

Supplemental insurance agents in Annapolis help residents choose Medigap policies or Medicare Advantage plans to cover gaps in Original Medicare. Maryland law requires agents to be licensed by the Maryland Insurance Administration. Agents can explain the annual open enrollment period and special enrollment rules specific to the state.

Frequently Asked Questions

What is a supplemental insurance agent in Annapolis?

A supplemental insurance agent is a licensed professional who helps clients buy Medigap or Medicare Advantage plans. They work with multiple carriers to find a plan that fits your needs and budget.

When can I enroll in a Medigap plan in Maryland?

In Maryland the Medigap open enrollment period starts when you are 65 and enrolled in Medicare Part B. This period lasts six months and guarantees issue of any Medigap policy regardless of health conditions.

Do Maryland agents charge fees for their services?

Most supplemental insurance agents in Maryland are paid by the insurance carrier not by the client. You typically do not pay a fee for their help in selecting a plan.

Supplemental Insurance Agents in Other Maryland 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.