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Medicare Checklist for The Villages

A solid Medicare decision starts with solid information. Almost every headache we untangle at a Villages kitchen table traces back to one missing detail: a drug left off a list, a specialist nobody checked, an HR letter that never got requested.

Work through this Medicare checklist before you compare plans. It takes about twenty minutes, and it is the same list we walk through with clients from Buffalo Ridge to Fenney.

  • What to gather before you compare plans
  • Deadlines you cannot afford to miss
  • Questions worth asking any agent
Quiet residential street near Spanish Springs in The Villages, Florida

Step 1

Gather your documents

  • Your red, white and blue Medicare card, or your Social Security confirmation letter
  • Your current insurance card and plan name, if you have coverage today
  • Any Annual Notice of Change letter a plan mailed you this fall
  • A creditable coverage letter from an employer, TRICARE or the VA
  • A rough estimate of household income, in case you may qualify for Extra Help

Step 2

List what you actually use

  • Doctors and hospital

    Primary care, every specialist you see, and which system you'd rather use: UF Health The Villages Hospital or AdventHealth Waterman in Tavares.
  • Prescriptions

    Exact drug names, dosages, how often you fill them, and your pharmacy. A photo of the bottles works fine if that's faster.
  • Care you expect to need

    A scheduled surgery, ongoing physical therapy or regular lab work should shape which plan makes sense this year.

Step 3

Know your dates

  • Your 65th birthday and the 7-month Initial Enrollment Period built around it
  • The month Part B starts, which opens your 6-month Medigap window
  • October 15 through December 7 for Annual Open Enrollment
  • January 1 through March 31 if you're already on a Medicare Advantage plan
  • Your last day of active employment, if you're delaying Part B

Not sure which window applies to you?

Read Turning 65 if Medicare is new to you, or Switch Your Plan if you're already enrolled and thinking about a change.

Step 4

Questions to ask any agent

A licensed, independent agent should answer each of these without hesitation: Which carriers are you appointed to sell? Are my doctors in-network on this exact plan for next year, not just this year? What will each of my prescriptions cost under this plan's formulary? What's my total expected cost for the year, not just the monthly premium? What happens if I need to switch later?

Vague answers mean it's time to keep looking. You can read about how we work or start with our Medicare FAQs.

Checklist finished? Let's compare plans.

Bring what you've gathered and we'll line up the plans we represent in Sumter, Lake and Marion counties, then explain which ones actually fit your doctors and prescriptions.