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Find Medicare Insurance Agents Near You in Annapolis, MD

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

The top-rated medicare insurance agent in Annapolis, Maryland is Mathes Insurance Advisors, Inc., rated 4.9 stars across 426 reviews. Other highly rated options include JSR Insurance, CNR Insurance Inc, Goosehead Insurance - Tim Coe. This directory lists 19 medicare insurance agents serving Annapolis.

Showing 19 medicare 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
5Old Bay Insurance Agency133 Defense Hwy #214(410) 777-5390
6East Coast Health Advisors619 Ridgely Ave #200(410) 896-1212
7Built For Life Financial Agency147 Old Solomons Island Rd Suite 200(240) 375-0404
8O'Brien & Associates339 Buschs Frontage Rd #206(410) 571-5900
9Reyes Insurance LLC1831 Forest Dr # A(443) 440-0989
10Bay Area Insurance1 Annapolis St STE 100(410) 647-7333
MI
2525 Riva Rd Suite 105
Mathes Insurance Advisors, Inc.
Medicare Insurance Agent · Annapolis, MD

Mathes Insurance Advisors, Inc. serves Annapolis and Anne Arundel County as a Medicare insurance agency. It helps clients understand their plan options during annual enrollment periods and when first qualifying for coverage. The agency guides individuals through the complexities of Original Medicare, Medicare Advantage, and Medicare Supplement plans. It assists with comparing prescription drug coverage plans to ensure medications are covered. This agency handles Medicare Part D enrollment and annual plan reviews for existing clients.

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

JSR Insurance provides guidance on Medicare insurance plans for individuals in the Annapolis area. The agency helps clients understand their options, including the differences between Medicare Advantage, supplement, and Part D drug coverage. It focuses on educating clients during enrollment periods and paperwork processes. JSR Insurance assists with annual plan reviews to ensure coverage remains aligned with healthcare needs. This service supports those with Medicare eligibility. The company services single-family homes, apartments, retail, and restaurants, helping their owners and employees navigate long-term health insurance decisions.

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

Serving Annapolis and the surrounding communities in Anne Arundel County, CNR Insurance Inc handles Medicare insurance planning for local seniors. The agency assists clients in navigating both Medicare Advantage plans and prescription drug coverage options. It also helps individuals understand Medicare Supplement policies to fill coverage gaps. All client jobs are approached with a thorough needs assessment and clear comparison of available plans for that year.

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

Homeowners and retirees in Annapolis, Maryland, turn to Goosehead Insurance - Tim Coe for guidance with Medicare insurance options. The agency helps clients navigate plan selection, including Medicare Supplement and Advantage choices, to align with individual healthcare needs and budgets. With a focus on clear explanations and personalized service, it assists customers through enrollment periods and coverage changes. The agency also serves communities throughout Anne Arundel County, including neighboring areas such as Severna Park and Arnold.

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

Old Bay Insurance Agency serves Annapolis, Maryland, and the surrounding communities, handling the full range of Medicare insurance options for local beneficiaries. This includes Medicare Advantage plans, Medicare Supplement policies, and Part D prescription drug coverage. The agency works to clarify the often complex enrollment periods and plan differences for each client. For a typical job, it begins with a detailed review of the individual’s current coverage and medical needs before presenting clear, side-by-side comparisons of available plans in the area.

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

East Coast Health Advisors, located in Annapolis, Maryland, assists clients by distinguishing between one-time plan selections and recurring service options, such as annual enrollment reviews. The agency guides individuals through the coverage details of Medicare Advantage, Part D drug plans, and Medigap policies, ensuring each choice aligns with local healthcare needs. Service is provided on a scheduled basis, typically around open enrollment periods or upon client request for a plan reassessment.

BF
147 Old Solomons Island Rd Suite 200
Built For Life Financial Agency
Medicare Insurance Agent · Annapolis, MD

Built For Life Financial Agency offers Medicare insurance guidance, helping clients in Annapolis navigate plan options like supplements and drug coverage. It assists with enrollment for both new beneficiaries and those looking to adjust existing policies. The agency works to match coverage to individual healthcare needs and budgets. It specifically helps with understanding the annual open enrollment period in the fall, ensuring seniors in the area address any last-minute plan changes before the deadline.

OB
339 Buschs Frontage Rd #206
O'Brien & Associates
Medicare Insurance Agent · Annapolis, MD

O’Brien & Associates, based in Annapolis, Maryland, provides Medicare insurance guidance to local beneficiaries. The firm specializes in helping clients navigate plan options such as Part D prescription drug coverage and Medicare Advantage. Its agents assist individuals in selecting plans that fit their healthcare needs and budgets. For commercial clients, the company also supports enrollment for businesses with groups that require Medicare-related solutions, including coverage for offices, warehouses, and food service operations.

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

During Medicare’s Annual Enrollment Period, Annapolis residents often seek clarity on plan changes. Reyes Insurance LLC, a local Medicare insurance agent, helps seniors evaluate their Part D and Advantage options. The agent reviews each client’s current coverage and prescription needs to identify suitable plans available in Anne Arundel County. Every consultation begins with a free, no-obligation inspection of the individual’s existing benefits and a careful assessment of upcoming enrollment deadlines.

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

Bay Area Insurance provides residential Medicare insurance guidance to clients in Annapolis, Maryland, helping individuals navigate plan options and enrollment periods. The company also offers commercial coverage solutions for local businesses seeking group Medicare-related products within the Annapolis area. Service is focused on Anne Arundel County and surrounding communities, ensuring accessibility for both individual policyholders and small enterprises. After an initial consultation and enrollment, the agency follows up prior to each annual open enrollment period to review plan changes and assist with any necessary adjustments between regular visits.

HM
2498 Riva Rd
Henry M Murray Insurance Agency
Medicare Insurance Agent · Annapolis, MD
(410) 224-2664
henrymurray.com
SB
108 Old Solomons Island Rd Bldg 2
Simpson and Blom Insurance
Medicare Insurance Agent · Annapolis, MD
(410) 573-9104
simpsonandblom.com
RS
2049 West St Suite 202
Ramsey's Insurance, Inc
Medicare Insurance Agent · Annapolis, MD
(410) 266-9363
ramseys-insurance.com
JM
111 Forbes St
Jack Martin Insurance Advisors
Medicare Insurance Agent · Annapolis, MD
(410) 263-8000
askjack.cc
EH
71 Old Mill Bottom Rd
Elite Health Insurance MD
Medicare Insurance Agent · Annapolis, MD
(410) 934-4536
IM
170 Jennifer Rd
Insurance Management Associates, Inc.
Medicare Insurance Agent · Annapolis, MD
(410) 873-9964
MP
133 Defense Hwy #214
Maryland Permanent Insurance
Medicare Insurance Agent · Annapolis, MD
(410) 777-5390
oldbayinsurance.com
HI
170 Jennifer Rd Suite 205
HUB International
Medicare Insurance Agent · Annapolis, MD
(410) 266-8888
hubinternational.com/offices/us/maryland/annapolis-jennifer-road
AI
60 West St Suite 61
Annapolis Insurance Advisors
Medicare Insurance Agent · Annapolis, MD
(443) 600-7400
annapolisinsuranceadvisors.com

What Does a 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.

About medicare insurance agents in Annapolis

Medicare insurance agents in Annapolis, Maryland help residents navigate Medicare Part A, Part B, Part C, and Part D plans. Maryland law requires agents to be licensed by the Maryland Insurance Administration. Local agents can explain the Annual Enrollment Period and Special Enrollment Period rules that apply to Anne Arundel County residents.

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.

Medicare Insurance Agents in Other Maryland 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.