Sign up for Medicare in Portland, CT

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

MedicareSignups.com Connecticut

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?

Portland, CT 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 06480, Non-smoker*
Plan Type Number of Plans Available Average Monthly Premium Lowest Monthly Premium Highest Monthly Premium Carriers
$0 OOP Medicare Advantage Plans 42 $0.00 $0.00 $0.00 Aetna Medicare, Anthem Blue Cross and Blue Shield, Cigna HealthCare
Paid Medicare Advantage Plans 14 $64.98 $2.30 $202.80 Aetna Medicare, Anthem Blue Cross and Blue Shield, Wellcare

*Plan data last updated on 1/15/2026

Most Popular Medigap Plans: Female, Age 65, Zipcode 06480, Non-smoker*
Plan Type Number of Plans Available Average Monthly Premium Lowest Monthly Premium Highest Monthly Premium Carriers
Plan F 10 $386.03 $312.00 $508.20 ConnectiCare, Omaha Insurance Company, Anthem Blue Cross and Blue Shield - Connecticut, and 7 others
Plan G 10 $347.44 $246.46 $461.94 ConnectiCare, Omaha Insurance Company, Anthem Blue Cross and Blue Shield - Connecticut, and 7 others
Plan N 9 $220.28 $176.32 $317.11 ConnectiCare, Omaha Insurance Company, Anthem Blue Cross and Blue Shield - Connecticut, and 6 others

*Plan data last updated on 1/15/2026

Most Popular Medigap Plans: Male, Age 65, Zipcode 06480, Non-smoker*
Plan Type Number of Plans Available Average Monthly Premium Lowest Monthly Premium Highest Monthly Premium Carriers
Plan F 10 $386.03 $312.00 $508.20 ConnectiCare, Omaha Insurance Company, Anthem Blue Cross and Blue Shield - Connecticut, and 7 others
Plan G 10 $347.44 $246.46 $461.94 ConnectiCare, Omaha Insurance Company, Anthem Blue Cross and Blue Shield - Connecticut, and 7 others
Plan N 9 $220.28 $176.32 $317.11 ConnectiCare, Omaha Insurance Company, Anthem Blue Cross and Blue Shield - Connecticut, and 6 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 Portland today

Walter Taylor Medicare Agent
Walter Taylor

Licensed Medicare Agent
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Portland, CT Medicare Resource Center

Portland Medicare Information

If you're looking to sign up for Medicare in Portland, CT, MedicareSignups.com is your go-to resource. Our comprehensive plan comparison tool simplifies the process of finding the perfect plan tailored to your needs. Remember, Medicare plans and options can vary significantly even at the zip code level, so it's essential to explore what's available in your local area. Interesting fact: Portland is home to the iconic Brownstone Quarries, which have supplied the brownstone for popular structures like Yale University and even parts of New York City! As you approach your 65th birthday or review your current Medicare options, let us assist you in discovering the best plans for your unique situation.

Enroll in a Portland Connecticut Medicare Plan.

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Portland, CT Local Medicare Offices

Connecticut Official State Health Insurance Assistant Program

Connecticut's official state SHIP program is the CHOICES Program. Maximizing opportunities for the independence and well-being of people with disabilities and older adults in Connecticut.

Visit the Official Website »

Local Portland, CT SHIP program official resource.

CHOICES Program is the official Connecticut state program that is dedicated to helping seniors living in Portland, CT with Medicare information, as well as an abundance of other resources for seniors.