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Compare Medicare Insurance Agents in Annapolis, MD

Directory of medicare insurance agents in Annapolis, Maryland. Verify credentials with the state department of insurance before hiring.

19 agents listed
Updated May 2026
Annapolis, MD
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 Maryland before hiring.
Showing 19 medicare insurance agents in Annapolis, MD Listings are displayed in no particular order and are not ranked by BeforeInsuranceUSA. Order does not constitute a recommendation or endorsement of any agent.
Mathes Insurance Advisors, Inc.
2525 Riva Rd Suite 105, Annapolis, MD 21401
(410) 295-9900 mathesinsurance.com
JSR Insurance
793 Fairview Ave, Annapolis, MD 21403
(443) 529-9109 jsrichardsoninsurance.com
CNR Insurance Inc
166 West St, Annapolis, MD 21401
(410) 897-9890 cnrinsurance.com
Goosehead Insurance - Tim Coe
1125 West St Suite 200, Office 244, Annapolis, MD 21401
(443) 924-6704 goosehead.com
Old Bay Insurance Agency
133 Defense Hwy #214, Annapolis, MD 21401
(410) 777-5390 oldbayinsurance.com
East Coast Health Advisors
619 Ridgely Ave #200, Annapolis, MD 21401
(410) 896-1212 eastcoasthealthadvisors.com
Built For Life Financial Agency
147 Old Solomons Island Rd Suite 200, Annapolis, MD 21401
(240) 375-0404 bflagency.com
Reyes Insurance LLC
1831 Forest Dr # A, Annapolis, MD 21401
(443) 440-0989 reyesinsuranceservices.com
O'Brien & Associates
339 Buschs Frontage Rd #206, Annapolis, MD 21409
(410) 571-5900 obrienandassoc.com
Bay Area Insurance
1 Annapolis St STE 100, Annapolis, MD 21401
(410) 647-7333 bayareains.com
Ramsey's Insurance, Inc
2049 West St Suite 202, Annapolis, MD 21401
(410) 266-9363 ramseys-insurance.com
Simpson and Blom Insurance
108 Old Solomons Island Rd Bldg 2, Annapolis, MD 21401
(410) 573-9104 simpsonandblom.com
Henry M Murray Insurance Agency
2498 Riva Rd, Annapolis, MD 21401
(410) 224-2664 henrymurray.com
Jack Martin Insurance Advisors
111 Forbes St, Annapolis, MD 21401
(410) 263-8000 askjack.cc
Elite Health Insurance MD
71 Old Mill Bottom Rd, Annapolis, MD 21409
(410) 934-4536
Maryland Permanent Insurance
133 Defense Hwy #214, Annapolis, MD 21401
(410) 777-5390 oldbayinsurance.com
Insurance Management Associates, Inc.
170 Jennifer Rd, Annapolis, MD 21401
(410) 873-9964
HUB International
170 Jennifer Rd Suite 205, Annapolis, MD 21401
(410) 266-8888 hubinternational.com
Annapolis Insurance Advisors
60 West St Suite 61, Annapolis, MD 21401
(443) 600-7400 annapolisinsuranceadvisors.com

What Does a Medicare Insurance Agent in Annapolis Cost?

Medicare insurance agents in Maryland typically do not charge you a fee for their services. They are paid by the insurance companies whose plans they sell. Medigap plan premiums in Annapolis can range from about $100 to $300 per month depending on your age and the plan type. Medicare Advantage plans often have low or zero monthly premiums but may have copays and deductibles. This is general information, 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 Annapolis do?
A Medicare insurance agent helps you compare Medicare Advantage, Medigap, and Part D prescription drug plans. They explain plan benefits, costs, and provider networks. Agents in Annapolis must follow Maryland insurance regulations and cannot charge you directly for their services.
When can I enroll in Medicare in Annapolis?
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. Maryland also offers a Special Enrollment Period for certain life events like moving or losing other coverage.
How do I choose a Medicare insurance agent in Annapolis?
Look for an agent licensed by the Maryland Insurance Administration. Ask if they represent multiple insurance companies so you can compare options. Check their experience with Medicare plans offered in Anne Arundel County.