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Explore Medicare Plans in Florida with Local Support You Can Trust

Navigating Medicare isn’t easy—especially with so many options and confusing terms like Parts A, B, C, D, and Medigap. At Living Tree Financial Group, we help Florida residents find the right Medicare coverage for their needs, whether you’re turning 65, on disability, or exploring better options during the Annual Enrollment Period.


As a trusted Medicare insurance agency in Winter Park, FL, we guide seniors and those with disabilities across Central Florida through their Medicare journey—from plan comparisons to enrollment and year-round support.

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Medicare Made Simple

Helping You Understand
the Medicare Maze

Medicare is a federal program, but your choices vary based on where you live, who your doctors are, and what coverage you need. That’s why we take time to explain the differences—and help you feel confident about your decisions.


We work with all types of Medicare clients:


  • Adults turning 65 and new to Medicare
  • Those under 65 with qualifying disabilities
  • People retiring early and needing help bridging coverage
  • Anyone overwhelmed by the process or unsure what they need

Understanding Your Medicare Choices

There are several paths through Medicare—and we’re here to help you find the one that fits your situation best. Here’s a quick breakdown:

01

Original Medicare (Parts A & B)

Hospital and medical coverage through the government. Does not include prescriptions or dental.

Learn More About Medicare A & B »

02

Medicare Advantage (Part C)

Bundled plans from private insurers that typically include medical, hospital, and drug coverage in one plan. May include extras like dental, vision, and gym memberships.

Learn More About Medicare Advantage Plans »

03

Medicare Supplement (Medigap)

Secondary coverage that helps pay the costs that Original Medicare doesn’t cover (like copays and deductibles).

Learn More About Medicare Supplement (Medigap) »

04

Medicare Part D

Prescription drug coverage that works with Original Medicare or with some Medicare Advantage plans.

Learn More About Medicare Part D »

Not sure where to begin? We’ll walk you through it in plain language, so you know exactly what you’re enrolling in—and what you’re not.

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Enrollment Essentials

When & How to Enroll in Medicare

Timing matters with Medicare, and missing the right enrollment window can result in penalties or delayed coverage.


Key enrollment periods include:


  • Initial Enrollment Period (IEP): Begins 3 months before your 65th birthday, and runs 3 months after.


  • Annual Enrollment Period (AEP): Runs from October 15 to December 7 each year. This is when you can switch or enroll in Medicare Advantage or Part D plans.


  • Open Enrollment Period (OEP): January 1 to March 31—for those already in Medicare Advantage who want to make one plan change.



Have questions about when you're eligible or whether you're in the right plan? We’ll review your timeline and help you take the right steps at the right time.

How We Help You Choose the Right Medicare Plan

There are over 20 Medicare plans available in Central Florida alone. Trying to compare them all on your own can be frustrating and time-consuming. That’s where we come in.


  • We’ll compare plans from multiple carriers—not just one or two.


  • We narrow your options down to the top 2–3 plans based on your doctors, prescriptions, budget, and preferences.


  • We handle the paperwork and enroll you directly.


  • We stay available for claims support, billing questions, or future plan changes.


Our agents are fully licensed in Florida and complete annual Medicare certifications (including AHIP training), so you’ll always get accurate, up-to-date advice—not a sales pitch.


We also offer free Medicare 101 workshops  throughout the year, designed to help you learn the basics in a relaxed setting. Contact us to ask about upcoming sessions.

Local Plans Matter

Why Local Medicare Help Makes a Big Difference

Choosing a plan from an online ad or a national call center might leave you with a policy that doesn’t cover your local doctors or nearby hospitals. That’s why it’s important to work with someone who knows the specific plan networks and costs in your zip code.


As a Winter Park-based Medicare broker, we serve:


  • Orange County (Winter Park, Orlando, Apopka)
  • Osceola County (Kissimmee, St. Cloud)
  • Polk County (Lakeland, Haines City)
  • Pasco County (Zephyrhills, Dade City)


We’ll help you understand what’s available right where you live—and explain your options in-person, over Zoom, or by phone. Whatever works best for you.

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Frequently asked questions

Frequently Asked Questions About Medicare in Florida

  • When can I sign up for Medicare?

    Most people are first eligible to enroll in Medicare around their 65th birthday. This Initial Enrollment Period starts three months before the month you turn 65 and ends three months after. If you're already receiving Social Security, you’ll usually be enrolled automatically. If not, you’ll need to sign up. If you miss this window, there are other enrollment periods, but you may face penalties or delays—so timing matters.

  • What’s the difference between Medicare Advantage and Original Medicare?

    Original Medicare (Parts A & B) is offered through the federal government. Medicare Advantage (Part C) plans are run by private insurance companies and include everything Original Medicare covers—and often more. Advantage plans may bundle in extras like dental, vision, and prescription drug coverage. Choosing between them depends on your healthcare needs, doctor preferences, and budget. We help you compare both.

  • Do I need a Medicare Supplement plan (Medigap) if I have a Medicare Advantage plan?

    No. You can only have one or the other—not both. Medicare Supplement plans help cover out-of-pocket costs if you stay with Original Medicare. Medicare Advantage plans often have lower premiums but may have copays or network rules. We’ll help you decide which path fits your needs best.

  • Does Medicare cover prescriptions?

    Not automatically. Original Medicare (Parts A & B) does not include prescription drug coverage. You can get it by enrolling in a standalone Part D plan or by choosing a Medicare Advantage plan that includes drug coverage (often called an MA-PD). We’ll help you check if your medications are covered under the plans available in your area.

  • How much does Medicare cost in Florida?

    Part A is usually free if you or your spouse worked and paid Medicare taxes. Part B has a monthly premium (most people pay a standard amount, but higher earners may pay more). If you choose a Part D or Medicare Advantage plan, costs vary by plan. We’ll walk through your options and help you estimate your total costs—including premiums, copays, and out-of-pocket maximums.

  • Can I keep my doctor with Medicare?

    That depends on the plan you choose. Original Medicare lets you see any doctor that accepts Medicare. Medicare Advantage plans often have networks, so it’s important to check whether your providers participate. Before you enroll, we’ll verify if your doctors are in-network.

  • What happens if I’m still working at 65?

    If you have employer coverage through a large company (20+ employees), you may be able to delay Medicare without penalty. If your employer is smaller or your coverage isn’t creditable, you might need to sign up. We’ll review your current insurance and help you decide what to do.

  • Is dental or vision covered by Medicare?

    Original Medicare doesn’t cover routine dental or vision care. Some Medicare Advantage plans do include those benefits. If not, we offer affordable standalone dental and vision plans that can be added alongside your Medicare coverage.

  • How do I enroll in a plan through Living Tree?

    We make it easy. Just give us a call at (321) 214-4594 or send us a message. We’ll set up a free consultation—by phone, Zoom, or in person at our Winter Park office—to review your needs and walk you through plan options.

Take the First Step Toward Confident Medicare Coverage

Help Starts Here

Not sure where to begin? You don’t have to figure it out alone.


Call us at   (321) 214-4594 or contact us here to schedule a Medicare consultation. We’ll help you compare plans, explain your options, and walk you through enrollment—all at no cost to you.

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