Sign up for Medicare in Chestertown, MD

Local licensed agents in Kent County are available to assist you if you need help comparing plans or registering for Medicare insurance.

MedicareSignups.com Maryland

Original Medicare

Original Medicare (Part A) covers most medically necessary services.

Medicare Supplement

Medigap plans provide additional insurance for out of pocket costs.

Medicare Advantage

A bundled alternative to Original Medicare for your health and drug coverage.

Not sure what Medicare plan is right for you?

Chestertown, MD Medicare Supplement Insurance Plan Comparison

First, decide between Traditional Medicare (which covers Parts A and B) and a private insurance's Medicare Advantage (known as Part C). If you go with Traditional Medicare, you'll probably also need a Medigap insurance to cover extra costs and a Part D plan for prescription drugs.

Medicare Advantage Plans: Age 65, Zipcode 21620, Non-smoker*
Plan Type Number of Plans Available Average Monthly Premium Lowest Monthly Premium Highest Monthly Premium Carriers
$0 OOP Medicare Advantage Plans 22 $0.00 $0.00 $0.00 CareFirst BlueCross BlueShield Medicare Advantage, UnitedHealthcare, Humana
Paid Medicare Advantage Plans 11 $36.18 $1.40 $90.80 CareFirst BlueCross BlueShield Medicare Advantage, Alterwood Advantage, Wellcare

*Plan data last updated on 1/15/2026

Most Popular Medigap Plans: Female, Age 65, Zipcode 21620, Non-smoker*
Plan Type Number of Plans Available Average Monthly Premium Lowest Monthly Premium Highest Monthly Premium Carriers
Plan F 23 $257.45 $182.82 $473.70 Insurance Company of North America, State Farm, Medico, and 20 others
Plan G 23 $212.66 $149.23 $396.09 Insurance Company of North America, State Farm, Medico, and 20 others
Plan N 23 $162.12 $111.48 $338.75 Insurance Company of North America, State Farm, Medico, and 20 others

*Plan data last updated on 1/15/2026

Most Popular Medigap Plans: Male, Age 65, Zipcode 21620, Non-smoker*
Plan Type Number of Plans Available Average Monthly Premium Lowest Monthly Premium Highest Monthly Premium Carriers
Plan F 23 $286.60 $207.24 $504.70 Insurance Company of North America, State Farm, Medico, and 20 others
Plan G 23 $236.18 $171.61 $422.04 Insurance Company of North America, State Farm, Medico, and 20 others
Plan N 23 $179.95 $125.54 $360.96 Insurance Company of North America, State Farm, Medico, and 20 others

*Plan data last updated on 1/15/2026

Disclaimer: The information provided in these tables is for general informational purposes only. We make no guarantees about the accuracy, completeness, or reliability of the data. Please consult with a professional advisor or insurance provider for precise and up-to-date information.

Need help? Speak to a licensed Medicare insurance agent in Chestertown today

Greg Faulcon Jr. Medicare Agent
Greg Faulcon Jr.

Licensed Medicare Agent
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Chestertown, MD Medicare Resource Center

Chestertown Medicare Information

If you're looking to sign up for Medicare in Chestertown, MD, MedicareSignups.com is your go-to resource. This website allows you to easily compare plans with its user-friendly tool, ensuring you find a plan that suits your individual needs. While Medicare is a national program, remember that plan options vary by location, even down to your zip code in Chestertown. Did you know that Chestertown is known for its annual Tea Party Festival, which commemorates a 1774 event where residents staged their own tea party protest against British taxes? Whether you're just turning 65 or already a Medicare beneficiary, MedicareSignups.com helps take the guesswork out of choosing healthcare coverage.

Enroll in a Chestertown Maryland Medicare Plan.

Enroll in a Chestertown Maryland Medicare Plan. Compare Plans »

Chestertown, MD Local Medicare Offices

Maryland Official State Health Insurance Assistant Program

Maryland's official state SHIP program is the Senior Health Insurance Assistance Program (SHIP). Welcome! The Maryland Department of Aging (MDoA) and the statewide network of 19 Area Agencies on Aging assist older Marylanders with a range of services and sources of information. MDoA administers state and federal programs, many of which are significantly lower in cost than nursing home placement. Choose a program listed to the left and click on its name to obtain helpful information. The list below includes a brief description of each MDoA program.

Visit the Official Website »

Local Chestertown, MD SHIP program official resource.

Senior Health Insurance Assistance Program (SHIP) is the official Maryland state program that is dedicated to helping seniors living in Chestertown, MD with Medicare information, as well as an abundance of other resources for seniors.