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Medicare help for Winter Haven, one call away

We can go through Medicare Advantage, Medigap and drug plans face to face by appointment, or by phone or Google Meet, at a time that works for you. I'm Jeannie Pond, licensed since 2009 and working from Lakeland, just west of you.

We do not offer every plan available in your area. Currently we represent 14 organizations which offer 52 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

1-800-MEDICARE (1-800-633-4227), TTY 1-877-486-2048, 24 hours a day/7 days a week

Start your request

What would you like help with?

Choose the one that fits best. You can tell me more on the call.

Where do you live?

Plans differ by county, so your ZIP code helps me get ready before I call.

5 digits

How should I reach you?

I need a phone number to call you. Email is optional.

Best time to call (optional)

Your go ahead

Both boxes are optional. Check any you're comfortable with, then send.

A licensed insurance agent will contact you.

A pale yellow three-story corner building with a street clock in downtown Winter Haven, palms along a brick sidewalk

Winter Haven's Social Security office on Havendale Boulevard is the one the locator lists first for Winter Haven, Haines City and Lake Wales. I'm Jeannie Pond, NPN 8940178, a Medicare agent in Lakeland, the same county, and I help people here compare Medicare Advantage, Medigap and Part D plans, meeting by appointment or working over the phone or Google Meet. Look up Winter Haven Hospital in any plan, and start early: your sign-up window usually opens three months before the month you turn 65.

Hi, I'm Jeannie Pond. If you live in Winter Haven, we can set an in-person appointment in Polk County, or do everything by phone or Google Meet. I've been licensed since 2009 and work from Lakeland as a Medicare agent: I'll ask about your doctors and prescriptions, look up the plans offered in Polk County, and walk you through the trade-offs until the choice makes sense to you.

Communities around Winter HavenInwoodCypress GardensJan Phyl VillageEagle LakeWahnetaLake Alfred

Winter Haven's growth and age, in four figures

  • 10,681Winter Haven residents 65 and olderCensus Bureau, ACS 2020-2024 (S0101), margin of error 774
  • 40.1median age in Winter HavenCensus Bureau, ACS 2020-2024 (S0101)
  • 62,313people in Winter Haven, up from 49,219 in 2020Census Bureau QuickFacts, 2025 estimate
  • 2,721veterans living in Winter HavenCensus Bureau QuickFacts

The Census Bureau figures for Winter Haven are survey estimates: table and margin of error sit under each number.

Where Winter Haven sits among the cities I coverMap of Polk County, Florida, with Winter Haven marked. From Winter Haven, the other cities I cover, nearest first: Auburndale to the northwest, Haines City to the northeast, Lake Wales to the southeast, Bartow to the southwest, Lakeland to the west and Plant City to the west. Winter Haven is drawn larger.
Winter Haven is the larger navy dot. Outlines from the Census Bureau.

Sign-up timing, the hospital and the east Polk office

  • First on the locator for three cities

    Searching ZIP 33880 on Social Security's office locator lists the office at 1395 NW Havendale Blvd first. The same office comes up first for Haines City and Lake Wales ZIP codes too, so if you need it, check the hours on ssa.gov or start online with a my Social Security account.

  • Look up Winter Haven Hospital first

    Winter Haven Hospital on Avenue F NE is in CMS Care Compare's list for the city. In an HMO you usually have to use the plan's network, while a PPO lets you go outside it and usually costs less inside it, according to Medicare.gov. So if this is your hospital, we see how each plan treats it, along with your doctors.

  • A city that keeps adding people

    The Census Bureau counted 49,219 people in Winter Haven in the 2020 Census and estimates 62,313 for 2025. If you're one of the newer arrivals and brought a Medicare plan from elsewhere, the move itself may give you a Special Enrollment Period, which Medicare.gov says runs until 2 full months after you move.

  • Turning 65 in Winter Haven: seven months to sign up

    Your Initial Enrollment Period generally lasts seven months, starting three months before you turn 65, according to Medicare.gov. I'd much rather we talk at the start of those months than the end, so there's time to compare without rushing.

The office east Polk shares, and Winter Haven Hospital

Government sources list these for Winter Haven. I'm not affiliated with any of them.

Social Security for Winter Haven

Social Security office, Winter Haven

1395 NW Havendale Blvd, Winter Haven, FL 33881

The first office Social Security's locator lists for ZIP 33880, Winter Haven's own.

See it on ssa.gov

Hospital to check

Winter Haven Hospital

Listed in Winter Haven by CMS Care Compare. Check it in each plan's provider directory; nothing here says which plans include it.

Free counseling for Winter Haven

SHINE

1-800-963-5337TTY 1-800-955-8770

SHINE's specially trained volunteers help Winter Haven residents with Medicare one on one. It's free and confidential, offered by the Florida Department of Elder Affairs with Polk's Senior Connection Center.

SHINE's website

Coming up on 65 in Winter Haven

Coming up on 65? Read my guide to the Medicare enrollment periods, then let's talk early in your window. I'll explain Medicare Advantage and Medigap in plain terms, and if you choose Original Medicare, we'll look for a Part D drug plan that covers your prescriptions.

If you're retiring before 65, I can also help with health insurance until Medicare starts.

We do not offer every plan available in your area. Currently we represent 14 organizations which offer 52 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

1-800-MEDICARE (1-800-633-4227), TTY 1-877-486-2048, 24 hours a day/7 days a week

Winter Haven sign-up questions

Where is the Social Security office in Winter Haven?

Social Security's locator lists it at 1395 NW Havendale Blvd, Winter Haven, FL 33881. Check its hours on ssa.gov before you go, or handle what you can online with a my Social Security account. Social Security's national number is 1-800-772-1213.

When should I call you if I'm turning 65 in Winter Haven?

Early in your Initial Enrollment Period, which Medicare.gov says starts three months before the month you turn 65 and runs seven months. That leaves time to compare plans and sign up without a deadline breathing down your neck.

Can you help me in Winter Haven if you're based in Lakeland?

Yes. We can meet in person by appointment or work by phone or Google Meet, and the plans we compare are the ones offered in Polk County, which is the same county for both of us.

Start early in your seven-month window

Send me a note or give me a call. I'll ask about your doctors and prescriptions, then we'll compare the plans offered in Polk County, side by side.

Jeannie Pond, Licensed Insurance Agent, NPN 8940178, licensed since 2009, based in Lakeland.

We do not offer every plan available in your area. Currently we represent 14 organizations which offer 52 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

1-800-MEDICARE (1-800-633-4227), TTY 1-877-486-2048, 24 hours a day/7 days a week

Call (888) 688-9919Ask Jeannie to reach out