Sign up for Medicare in Middlebury, CT
Local licensed agents in New Haven County are available to assist you if you need help comparing plans or registering for Medicare insurance.
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?
Middlebury, 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 06762, 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 | $67.48 | $2.90 | $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 06762, 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 06762, 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 Middlebury today

Gavin Foley
Licensed Medicare Agent
Contact Gavin through Medicare Agents Hub »
Middlebury, CT Medicare Resource Center
Middlebury Medicare Information
If you're looking to sign up for Medicare in Middlebury, CT, MedicareSignups.com simplifies the process with its easy-to-use plan comparison tool. This feature helps you explore and compare various Medicare plans specific to your zip code, underscoring the importance of local choice despite Medicare's national framework. Middlebury, known for its tranquil beauty and family-friendly community, is home to Quassy Amusement Park, one of America's oldest, running since 1908. As you approach your Medicare enrollment, remember that plan options can vary significantly, so taking advantage of localized comparisons ensures you find a plan that best suits your individual needs.
Enroll in a Middlebury Connecticut Medicare Plan. Compare Plans »
Middlebury, 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.





