Protecting your foundation through

Connect With Us Today

Health Insurance & Medicare Plans in Winter Park, FL

Finding the right Medicare or health insurance plan shouldn’t feel overwhelming. At Living Tree Financial Group we help you explore Medicare plans and health insurance options in Winter Park, FL, and across Central Florida—with trusted, local agents by your side every step of the way.

The Insurance Team Central Florida Families Count On

Living Tree Financial Group is proudly headquartered in Winter Park, Florida, and serves a wide range of communities across Orange, Osceola, Seminole, Lake, Marion, Polk, Pasco, and Volusia counties. Our team of licensed agents is committed to meeting you wherever you feel most comfortable, whether it's at our office, your home, a local coffee shop, or even over Zoom.


Additionally, we are licensed in several other states, including Alabama, Georgia, Louisiana, Mississippi, North Carolina, South Carolina, Tennessee, Ohio, Texas, Virginia, Michigan, and New York, through our extensive multi-state team of licensed professionals.

Get Help With Medicare, Health Plans, Life Insurance & More

Whether you're aging into Medicare, enrolling through the Marketplace, or protecting your family with life coverage, we’re here to help with a personalized, stress-free process.

Our Services

New to Medicare or reviewing your options? We simplify Advantage, Supplement (Medigap), and Part D plans so you can choose with confidence. Explore Medicare plans

Protect what matters most with affordable term life, whole life, and annuity products tailored to your goals. Learn more about life & annuity options

an older man is hugging a younger woman
A man is holding a baby in his arms and the baby is sticking out his tongue.

We help individuals, families, and small businesses navigate ACA Marketplace coverage and group plan options. Compare health insurance

Looking for extra coverage? We offer affordable ancillary insurance that fits your budget. View additional plans

Professional, no-fuss help during tax season. Get tax prep support

Who We Are

Why Central Florida Chooses Living Tree

We’ve been helping families since 2007—and we don’t disappear after enrollment. Our independent agency represents multiple top-rated carriers, giving you more choices and unbiased recommendations. All of our agents are licensed and AHIP-certified, and we’ll help you narrow your options to the best 2–3 plans based on your budget, doctors, prescriptions, and more.



Need help filing a claim or changing your plan months later? Just call—we’re here for the long haul.

Don’t Miss These Enrollment Deadlines

  • Medicare Annual Enrollment Period (AEP): Starts October 15
  • ACA Health Insurance Open Enrollment: Starts November 1
A group of people are planting a plant in the dirt.

Who We Serve

Individuals & High Net Worth Families

A black and white drawing of two people holding a baby.

Medicare Beneficiaries

Self-Employed Individuals

Executives

(realtors, lawyers, doctors)

A black and white drawing of an office chair on a white background.

Small Business Owners

And More!

Licensed in Florida & Across Other States

From Winter Park we serve families across Central Florida with in-person and virtual options. We also support clients in other states: Alabama, Georgia, Louisiana, Mississippi, Ohio, North Carolina, South Carolina, Tennessee, Texas, Virginia, and Michigan and can meet you virtually if needed.

Let’s Talk—We’re Easy to Reach

Contact Us Today!