Medicare in Winter Park · Orange County, FL
2026 Medicare Advantage Plans in Winter Park, FL
Orange County offers 94 Medicare Advantage plans for 2026 across 7 carriers, with an average premium of $11.5/mo and 66 plans rated 4★ or higher by CMS.
Winter Park (Orange County), FL has 94 Medicare Advantage plans (avg $11.50/mo) for plan year 2026.
Why Choose a Local Medicare Agent?
- Independent — not tied to any one carrier
- Licensed in NC, SC, GA, FL, VA, MD, MI, KS, TX, OH
- Free to you — agents are compensated by carriers
By the numbers · Orange County
Quick facts for Winter Park, FL Medicare (2026)
Health profile · why coverage choice matters here
Chronic conditions among Orange County adults
Source: County Health Rankings & Roadmaps 2024 — Orange County.
Find Medicare plans near you
Free tools
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Part B Late Enrollment Penalty
Monthly penalty: $0.00
IRMAA Quick Check
Monthly surcharge: $0.00
Who covers you
Carriers in Orange County (2026)
- UnitedHealthcare HMO-POSPPOD-SNP
AARP Medicare Advantage HMO-POS and PPO; D-SNP available statewide; one of FL's largest MA carriers
- Humana HMO-POSPPO
HMO-POS and PPO with one of Florida's largest provider networks; very strong in FL
- Aetna (CVS Health) HMOPPO
Medicare Signature PPO and HMO; strong star ratings across Florida
- Florida Blue (Guidewell) HMOPPO
Blue Cross Blue Shield of Florida; strong PPO and HMO network statewide
- Wellcare by Centene HMOD-SNP
Low-premium HMO and D-SNP plans; very competitive across Florida markets
- Devoted Health HMO
Florida-focused HMO with concierge model; strong in most FL markets
- Simply Healthcare (Anthem) D-SNP
Anthem subsidiary with strong Tampa Bay area network; D-SNP available
Where you get care
Hospitals & providers nearby
- Orlando Health Regional Medical Center 52 W Underwood St, Orlando FL 32806
- AdventHealth Orlando 601 E Rollins St, Orlando FL 32803
- HCA Florida Osceola Hospital 700 W Oak St, Kissimmee FL 34741
Confirm your doctors and preferred pharmacy are in-network before enrolling — networks vary by plan and carrier.
Sources: CMS Hospital Compare · CMS Landscape (PY2026).
Choosing a Medicare plan in Winter Park, FL — what matters here
- Winter Park is an affluent Orange County city known for its Rollins College campus and brick-paved Park Avenue. 94 Medicare Advantage plans for 2026, averaging $11.50/month.
- AdventHealth Winter Park (4 stars) and AdventHealth Orlando (5 stars) are both accessible. 44 SNPs serve dual-eligible beneficiaries.
Not sure Medicare Advantage is the right path?
Also consider Original Medicare + a Supplement
Medicare Advantage isn't the only option. If you want the freedom to see any doctor or hospital in the U.S. that accepts Medicare — with no networks, no referrals, and no plan-specific prior authorizations — a Medicare Supplement (Medigap) plan paired with a standalone Part D drug plan may be a better fit for your situation.
- No networks. See any Medicare-accepting provider nationwide — critical if you travel, split time between states, or have specialists outside your county.
- Predictable costs. Plan G covers nearly every gap in Original Medicare except the Part B deductible (~$257/yr in 2026). No surprise bills from out-of-network care.
- Enrollment window. Your guaranteed-issue Medigap Open Enrollment Period is 6 months from your Part B effective date. After it closes, health underwriting may apply in NC.
Medigap guide for Winter Park → NC Medicare Supplement overview →
Resources
Medicare guides for Winter Park, FL
What Is Medicare? Parts A, B, C & D Explained for 2026
Medicare has four parts that work together — and choosing the wrong combination at 65 can follow you financially for the rest of your life. A plain-English guide to what each part covers, what it costs, and how to enroll on time.
Read →
Medicare Advantage vs. Medigap in 2026: Which Is Right for You?
Two paths through Medicare — one bundles everything into a private plan, the other fills Original Medicare's gaps. The right choice depends on your health, your doctors, and a one-time enrollment window most people don't know about.
Read →
How to Avoid Medicare Late Enrollment Penalties in 2026
Miss a Medicare enrollment window and you pay a permanent surcharge added to your premiums for life. Here's exactly when to enroll in Parts A, B, and D — and the one exception that lets you delay without penalty.
Read →Winter Park, FL Medicare questions, answered
How many Medicare Advantage plans are available in Winter Park, FL?
For 2026, there are 94 Medicare Advantage plans available in Winter Park (Orange County), offered by 7 carriers including UnitedHealthcare, Humana, Aetna (CVS Health), and others. 66 of those plans carry a CMS star rating of 4★ or higher. Source: CMS PY2026 Landscape.
What is the average Medicare Advantage premium in Winter Park for 2026?
The average monthly Medicare Advantage premium in Winter Park, FL is $11.5 for 2026, with an average CMS star rating of 4★ across available plans. Premiums and benefits vary — compare your specific options at Medicare.gov or with a licensed agent.
When can I change my Medicare plan in Winter Park?
The Annual Enrollment Period (AEP) runs October 15 – December 7 each year and is the main window to switch Medicare Advantage plans, change Part D drug plans, or return to Original Medicare. Changes take effect January 1. The Medicare Advantage Open Enrollment Period (January 1 – March 31) allows one plan switch for those already in Medicare Advantage. Special Enrollment Periods are available for qualifying events such as moving or losing other coverage.
Are there Special Needs Plans available in Orange County?
Yes — Orange County has 44 Special Needs Plans (SNPs) available for 2026. These plans are designed for dual-eligible beneficiaries (Medicare + Medicaid), people in institutions, and those with qualifying chronic conditions. SNPs often carry $0 premiums and additional chronic care benefits. A licensed agent can confirm your eligibility at no cost.
What hospital options are near Winter Park, FL?
Orlando Health Regional Medical Center in Orlando is rated 4★ by CMS Hospital Compare; AdventHealth Orlando in Orlando is rated 5★ by CMS Hospital Compare; HCA Florida Osceola Hospital in Kissimmee is rated 3★ by CMS Hospital Compare. Before enrolling in any Medicare Advantage plan, confirm your hospital and doctors are in that plan's network.
Is there a cost for help choosing a Medicare plan in Winter Park?
No. Our guidance is free — licensed agents are compensated by the insurance carriers, not by you. We compare the plans available in your ZIP code against your doctors, prescriptions, and budget. We do not offer every plan available in your area. Contact Medicare.gov or 1-800-MEDICARE to see all options.
Is Medicare coverage the same in Winter Park, FL?
Original Medicare (Part A and Part B) is a federal program, so its core coverage rules are the same in Winter Park, FL as anywhere else in the country. What varies locally is which Medicare Advantage, Part D, and Medigap plans are actually offered — plan availability, provider networks, and premiums are set at the county level, so the specific options in Orange County won't match a different county even in the same state. That's why it's worth reviewing your local plan lineup each year rather than assuming coverage is identical everywhere.
When can I enroll in Medicare in Winter Park, FL?
Your Initial Enrollment Period (IEP) is a 7-month window centered on your 65th birthday — 3 months before, the month of, and 3 months after. After that, the Annual Enrollment Period (AEP) runs October 15 through December 7 each year, letting Winter Park residents switch Medicare Advantage or Part D plans for coverage starting January 1. A Special Enrollment Period (SEP) may also open outside these windows if you have a qualifying life event, such as moving to Winter Park or losing other health coverage.
How do I find a Medicare agent near Winter Park, FL?
Look for a licensed, independent agent who is appointed to sell plans in FL and familiar with the carriers and provider networks serving Orange County. An independent agent can compare options across multiple carriers instead of representing just one. You can book a free, no-obligation consultation with a licensed agent serving Winter Park through this site's contact page, or call the number listed on this page to talk with someone directly.
Is there a Medicare agent in Winter Park, FL?
Yes. Kayla Price is a licensed independent insurance agent serving Winter Park, FL and Orange County among the NC, SC, GA, FL, VA, MD, KS, TX, OH & MI she's licensed in. She works with 7 carriers offering plans in Orange County, so she can compare options rather than represent just one company. You can book a free consultation directly at https://host.safemsngr.com/widget/booking/A0NTF4B4d9I3h3wNvyIB.
How do I find Medicare help in Winter Park?
The fastest way is to book a free, no-obligation review with a licensed agent who already works in Orange County — Kayla Price at Price Services Group covers Winter Park, FL and can walk through the 94 Medicare Advantage plans available here for 2026. Schedule a time at https://host.safemsngr.com/widget/booking/A0NTF4B4d9I3h3wNvyIB, or use the contact page on this site. You can also always compare plans yourself at Medicare.gov or by calling 1-800-MEDICARE.
Does Price Services Group serve Winter Park, FL?
Yes — Winter Park, FL is within Kayla Price's real service area at Price Services Group. She is licensed in NC, SC, GA, FL, VA, MD, KS, TX, OH & MI and works with the carriers offering Medicare Advantage, Part D, and Medigap plans in Orange County. Book a free plan review at https://host.safemsngr.com/widget/booking/A0NTF4B4d9I3h3wNvyIB to see what's available at your address.
What Medicare Advantage plans are available in Winter Park, FL?
Medicare Advantage plan availability varies by county in FL. Kayla Price can review all plans available in Winter Park and help you compare options by phone or video.
How much does Medicare cost in Winter Park, FL?
Medicare Part B costs $202.90 per month regardless of where you live in FL. Additional costs depend on which plan you choose. Kayla can walk you through all the costs for plans available in Winter Park.
When is the next Medicare enrollment period for residents of Winter Park, FL?
The Annual Enrollment Period (AEP) runs October 15 through December 7 each year for all Medicare beneficiaries including those in Winter Park, FL. If you're new to Medicare, your Initial Enrollment Period is based on your 65th birthday.
Nearby coverage
Medicare help near Winter Park
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82 Medicare Advantage plansMore reading
Medicare topics for Orange County
Medicare Advantage Plans in Orange, FL 2026
See how the 94 Medicare Advantage plans available in Orange County compare on premium, star rating, and network for 2026.
Read on our blog →How to Avoid Medicare Penalties in Winter Park
Late Part B and Part D penalties are permanent. Here's how Winter Park, FL residents can enroll on time and avoid them.
Read on our blog →Best Medicare Supplement Plans for Orange Residents
A look at how Medigap Plan G and other supplement options stack up for Orange County Medicare beneficiaries.
Read on our blog →Enrollment windows
When can you change your Medicare plan?
Annual Enrollment Period
Oct 15 – Dec 7
Switch MA plans, add or drop Part D, or return to Original Medicare. Changes take effect January 1.
MA Open Enrollment Period
Jan 1 – Mar 31
One plan switch if you're already in Medicare Advantage. Changes start the first of the following month.
Initial Enrollment Period
7-month window at 65
3 months before, the month of, and 3 months after your 65th birthday. Enrolling on time avoids lifetime Part B and Part D penalties.
Your local agent
Talk to a licensed Medicare agent about Winter Park, FL plans
Kayla Price is a licensed, independent agent who works with 7 carriers serving Orange County — free, no pressure. We do not offer every plan available in your area.
We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or call 1-800-MEDICARE (1-800-633-4227), TTY 1-877-486-2048, 24 hours a day, 7 days a week, to get information on all of your options. Not affiliated with or endorsed by the U.S. government or the federal Medicare program. For informational purposes only — not insurance, legal, or financial advice. Plan availability, premiums, and benefits are based on CMS PY2026 data and subject to change. NPN: 18530055. Agency NPN: 20387435.