Winter Park has 15 state-licensed assisted living communities: 8 larger communities and 7 small residential homes (16 or fewer residents). The median cost of assisted living in Florida is $5,610 a month (CareScout 2025), against $6,200 nationally.
Most communities don't publish prices. Tell us who you're looking for and a local advisor will send current rates and availability for the assisted living options that fit.
Both are licensed by Florida as assisted living. Larger communities suit people who want social life and on-site services; small homes suit people who do better with quiet, familiar routines, including many people with dementia. Florida words these licenses as “Assisted Living Facility” (15).
Every assisted living community Florida licenses in Winter Park, from state records. Being listed is not a rating: Lilisity scores only communities with verified interviews (the Top Communities). Communities with verified reviews are listed first, then by size.
15 shown
| Community | Size | Price |
|---|---|---|
| Westchester of Winter Park558 North Semoran Blvd | Large121 residents | Get pricing |
| Watercrest Winter Park Assisted Living and Memory Carememory care1501 Glendon Parkway | Large118 residents | Get pricing |
| Summer Time ALF, INC.909 North Wymore Road | Large114 residents | Get pricing |
| Allegro2701 Howell Branch Rd | Large105 residents | Get pricing |
| Westminster Winter Parkmemory care1111 South Lakemont Avenue | Large73 residents | Get pricing |
| Mayflower Assisted Living Facilitymemory care1620 Mayflower Court | Large55 residents | Get pricing |
| Aiden Springs5520 Howell Branch Road | Mid-size25 residents | Get pricing |
| Alabama Oaks of Winter Park1759 Alabama Drive | Mid-size19 residents | Get pricing |
| Fremont Manor909 Fremont Avenue | Small home12 residents | Get pricing |
| Prevail Homes Residential Assisted Living Facility1315 Devon Rd | Small home8 residents | Get pricing |
| Hibiscus Oaks, LLCmemory care1385 Hibiscus Ave | Small home6 residents | Get pricing |
| Lotus Home of Winter Park LLC2030 Hidden Cove | Small home6 residents | Get pricing |
| Marie's Manor Assisted Living 2, LLC7612 Waunatta Ct | Small home6 residents | Get pricing |
| Maries Manor, INC4934 Seminole Ave | Small home6 residents | Get pricing |
| The View at Winter Park, INC.1047 Princess Gate Blvd | Small home6 residents | Get pricing |
The median cost of assisted living in Florida is $5,610 a month ($67,320 a year), below the national median of $6,200. That’s CareScout’s 2025 survey, collected July to November 2025. Small residential homes often cost less than larger communities, though care needs, room type and services move the price more than the building does.
Medicare does not pay for assisted living. People pay from savings and income, long-term care insurance, or VA Aid and Attendance (up to $29,093 a year for a veteran in 2026), and some qualify for Medicaid help with care costs at communities that accept it. Who actually pays for long-term care.
Free tools: how long will the money last? · home care or assisted living? · VA Aid and Attendance estimator
From 22,911 concerns residents and families raised in Senior Living Alliance phone interviews, the most common are about dining, housekeeping and hearing back from management.
All 8 tour questions, with a free printable tour card (PDF).
Florida publishes licensing records, and in most cases inspection or complaint reports, for every community on this page. Look up any community on the state’s site: quality.healthfinder.fl.gov. Ask the community for its most recent inspection report too; they have to keep it.
Florida licenses 15 assisted living communities in Winter Park as of September 2026: 8 larger communities and 7 small residential homes of 16 or fewer residents, with about 680 licensed spots in all.
The median cost of assisted living in Florida is $5,610 a month (CareScout 2025), compared with $6,200 nationally. Prices vary with the room, the level of care and the community, so ask each one for its current rate sheet, or ask a Lilisity advisor for current prices.
Medicaid doesn't pay rent or meals in assisted living. Most states offer a Medicaid waiver or program that can pay for care services at participating communities for people who qualify; not every community takes it, so ask each one. Florida's Medicaid agency or your local Area Agency on Aging can tell you what's available.
Florida publishes its licensing records at quality.healthfinder.fl.gov. You can also ask any community for its most recent state inspection report.
One call covers which communities have openings, what they cost and which fit your parent's needs and budget.
