Medicare at 65 While Still Working in Bedford, VA

Understanding how Medicare works if you continue working past age 65.

Many people continue working after turning 65 and may already have health insurance through an employer. Croft Insurance Services, Inc. helps individuals in Bedford review how Medicare works alongside employer coverage so they can decide when to enroll and how to avoid potential penalties.


If you are turning 65 but plan to keep working, it is important to understand how Medicare coordinates with employer insurance and when enrollment may be required.

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Do You Need Medicare at 65 If You Are Still Working?

Whether you need to enroll in Medicare at age 65 often depends on the type of employer coverage you have.


In many cases, individuals who are still working and covered by a qualifying employer health plan may be able to delay certain parts of Medicare without penalty.


However, the rules can vary depending on factors such as:


  • The size of your employer
  • Whether the coverage is through your own employer or a spouse’s employer
  • Which parts of Medicare you plan to enroll in


If you are unsure how your employer coverage interacts with Medicare, Croft Insurance Services, Inc. can review your situation and help you understand your options.

When you turn 65, you become eligible for Medicare Parts A and B. Many people automatically qualify for premium-free Part A, which covers hospital services.


Some individuals choose to enroll in Part A while continuing employer coverage, while delaying Part B until they retire or lose employer coverage.


Because enrollment decisions can affect future eligibility and penalties, it is important to review how these parts coordinate with your current health plan.



Our Bedford Medicare advisors walk through these details so you can make an informed decision based on your situation.

Understanding Medicare Parts When You Are Still Employed

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Employer Size and Medicare Rules

Employer size can affect how Medicare and your workplace health insurance work together.


In general:


  • Larger employers may allow employees to delay Medicare enrollment while maintaining employer coverage
  • Smaller employer plans may require Medicare to become primary coverage at age 65


Understanding how these rules apply to your specific plan helps ensure you maintain the coverage you need without unexpected gaps.

Avoiding Medicare Late Enrollment Penalties

One of the most common concerns for people working past 65 is avoiding Medicare late enrollment penalties.



Delaying enrollment may be allowed when you have qualifying employer coverage, but documentation and timing are important. Our team reviews your current health insurance to confirm whether it qualifies for delaying Medicare enrollment, explains when your Medicare Special Enrollment Period would begin after leaving employer coverage, and helps ensure you have the proper documentation when it is time to enroll.


Taking time to review these details now can help prevent penalties and protect your future Medicare options.

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Local Office in Bedford:

When you call Croft Insurance Services, Inc., you reach a local Bedford office — not a national call center.

Serving Virginia Clients Since 2004:

For more than two decades, we have helped individuals navigate Medicare decisions with steady guidance.

registered social security analyst:

Our team includes a Registered Social Security Analyst who can help review how Medicare decisions may align with retirement planning.

Year-Round Support:

We assist clients before enrollment, during the Medicare transition, and throughout the year if coverage questions arise.

Why Work With Croft Insurance Services, Inc.?

Schedule a Consultation

Meet Our Team

If you are approaching age 65 and still working, we can review how Medicare works with your employer coverage and help you plan the next step.

  • Melody Key

    A smiling person wearing a dark pinstriped blazer, white top, and silver necklace against a black curtain background.

    President & Broker


    Specializes in Medicare and health insurance guidance with year-round client support.

    Schedule with Melody

  • Les Plymale

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    Vice President, Broker & Registered Social Security Analyst


    Provides Medicare enrollment coordination and structured benefit guidance.

    Schedule with Les

  • Ann Ogden

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    Insurance Broker


    Assists clients with Medicare plan comparisons and enrollment support.

    Schedule with Ann

Or call our Bedford office directly at 540-586-3500.

Frequently Asked Questions About Medicare While Working

  • Do I have to enroll in Medicare when I turn 65 if I am still working?

    Not always. If you have qualifying employer health insurance, you may be able to delay certain parts of Medicare.

  • Can I keep my employer health insurance after turning 65?

    Many people continue using employer coverage while working. Medicare enrollment requirements may depend on the type of plan and employer size.

  • Should I enroll in Medicare Part A while working?

    Some individuals choose to enroll in Part A if it is premium-free, but it is important to review how it coordinates with employer coverage.

  • What happens if I delay Medicare too long?

    Delaying enrollment without qualifying coverage could result in late enrollment penalties.

  • How do I enroll in Medicare when I retire?

    If you delayed enrollment due to employer coverage, you may qualify for a Special Enrollment Period to enroll without penalty.

Explore Your Options Today

Turning 65 and Still Working?

Croft Insurance Services, Inc. helps individuals in Bedford review how Medicare coordinates with employer health insurance so they can make confident enrollment decisions.


Call our Bedford office or schedule a consultation with a licensed Medicare advisor to review your situation.