Medicare at 65: What to Know Before You Enroll

Written by Canty Financial - Published on October 26, 2025
As you approach age 65, Medicare becomes a major part of your retirement healthcare planning. The rules can feel confusing at first — especially around enrollment timing, what’s covered (and what’s not), and how Medicare works if you’re still employed. Below is a clear, practical overview to help you understand the essentials before making any decisions.

1. When Does Medicare Start?

Most people become eligible at age 65.
Your Initial Enrollment Period lasts seven months:

  • The 3 months before your 65th birthday
  • The month you turn 65
  • The 3 months after

Delaying enrollment without other qualifying coverage can lead to lifetime late penalties for both Part B and Part D. Some individuals also qualify before 65 if they receive Social Security disability benefits or have End-Stage Renal Disease.

2. The Four Parts of Medicare

Part A – Hospital care, inpatient stays, skilled nursing, and hospice. Usually no premium.
Part B – Doctor visits, outpatient care, and preventive services. Monthly premium required (IRMAA may apply for higher incomes).
Part C (Medicare Advantage) – Private insurance plan that bundles Part A and B and often prescription coverage, plus extras like dental/vision/hearing.
Part D – Prescription drug coverage if not included in a Medicare Advantage plan.

3. What If You’re Still Working at 65?

Your employer size determines whether you should delay or enroll:

Employers with 20 or more employees

  • You can delay Part B without penalty.
  • Many people enroll in Part A only.
  • Important: If you contribute to an HSA, enrolling in Part A stops your eligibility to continue contributions.

Employers with fewer than 20 employees

  • Medicare becomes primary insurance by law.
  • In nearly all cases, you should enroll in both Part A and Part B to avoid gaps in coverage.

4. What Medicare Does Not Cover

Original Medicare (Parts A & B) does not cover:

  • Long-term custodial care (nursing home or assisted living)
  • Routine dental care
  • Eye exams for glasses
  • Dentures
  • Cosmetic surgery
  • Most acupuncture services
  • Hearing aids and related exams
  • Routine foot care (unless medically necessary)
  • Care received outside the United States

These gaps are part of the reason many retirees choose an Advantage or Medigap plan.

5. Medicare Advantage vs. Medigap

Once enrolled in Medicare, most retirees choose one of these two paths:

Medicare Advantage (Part C)

  • Works through a provider network (HMO/PPO)
  • Usually includes prescription coverage
  • Often includes dental/vision/hearing
  • Lower premiums, but more cost-sharing at the point of care

Medigap (Supplement Insurance)

  • Pairs with Original Medicare (Parts A & B)
  • Allows you to see any provider nationwide who accepts Medicare
  • Covers deductibles and copays for more predictable costs
  • Requires a separate Part D plan for prescriptions

Final Thoughts

Medicare decisions are highly individual — the right choice depends on your health needs, whether you travel, whether you’re still working, and whether extra benefits like dental or hearing coverage are important to you.

Planning ahead before turning 65 helps ensure you avoid penalties and select the structure that fits your situation best.

If you have questions about transitioning into Medicare or coordinating it with employer coverage, we are happy to help you walk through your options.

Canty Financial Management

Bill Canty, CFP®, CPA, Financial Planner

Ed Canty, CFP®, Financial Planner

Joe Canty, CFP®, Financial Planner

Tina Alteri, CPA, Tax Advisor

Maureen Walsh, EA, Tax Advisor

 

 

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