Assisted Living in Winter Park, FL
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.
Free guide · 14 pages
Choosing Assisted Living
A practical guide for families, with checklists to take on your tours.
- What assisted living costs and the ways to pay
- Signs it may be time
- Tour checklists to print and take with you
- What residents and families told us matters most
Two kinds of assisted living in Winter Park
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).
All 15 licensed assisted living communities in Winter Park
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 testimonials are listed first, then by size.
15 shown
| Community | Size | Price |
|---|---|---|
| Westchester of Winter Park558 North Semoran Blvd | Large121 residents | $3,500 to $5,650/moLilisity estimate |
| Watercrest Winter Park Assisted Living and Memory Carememory care1501 Glendon Parkway | Large118 residents | from $5,550/mo |
| Summer Time ALF909 North Wymore Road | Large114 residents | $3,500 to $5,650/moLilisity estimate |
| Allegro2701 Howell Branch Rd | Large105 residents | $3,500 to $5,650/moLilisity estimate |
| Westminster Winter Park (Independent Living and Assisted Living and Memory Care and Continuing Care)memory care1111 South Lakemont Avenue | Large73 residents | $3,500 to $5,650/moLilisity estimate |
| Mayflower Assisted Living Facilitymemory care1620 Mayflower Court | Large55 residents | $3,500 to $5,650/moLilisity estimate |
| Aiden Springs5520 Howell Branch Road | Mid-size25 residents | $3,500 to $5,650/moLilisity estimate |
| Alabama Oaks of Winter Park1759 Alabama Drive | Mid-size19 residents | $3,500 to $5,650/moLilisity estimate |
| Fremont Manor909 Fremont Avenue | Small home12 residents | $3,500 to $5,650/moLilisity estimate |
| Prevail Homes Residential Assisted Living Facility1315 Devon Rd | Small home8 residents | from $1,000/mo |
| Hibiscus Oaksmemory care1385 Hibiscus Ave | Small home6 residents | $3,850 to $6,200/moLilisity estimate |
| Lotus Home of Winter Park2030 Hidden Cove | Small home6 residents | $3,850 to $6,200/moLilisity estimate |
| Marie's Manor Assisted Living 27612 Waunatta Ct | Small home6 residents | $3,850 to $6,200/moLilisity estimate |
| Maries Manor4934 Seminole Ave | Small home6 residents | $3,850 to $6,200/moLilisity estimate |
| The View at Winter Park1047 Princess Gate Blvd | Small home6 residents | $3,850 to $6,200/moLilisity estimate |
Independent living in Winter Park
Also in Winter Park: 3 independent living, life plan and 55+ communities in Winter Park and 1 income-restricted senior apartment building.
How much does assisted living cost in Winter Park?
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. 2 Winter Park communities publish a starting price on Lilisity, from $1,000 to $5,550 a month. If more care is needed: nursing home costs in Florida, with CareScout medians and the private-pay rates nursing homes publish. 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
Three questions to ask on every Winter Park tour
From about 23,000 concerns residents and families raised in Senior Living Alliance phone interviews, the most common are about dining, housekeeping and hearing back from management.
- Can I come back and eat a meal here, unannounced?Dining was 23% of all concerns: quality that changes day to day.
- How is laundry labeled and tracked, and what happens when something goes missing?Housekeeping was 17%.
- Who is my main contact, and how often will I hear from them?Communication with management was 15%.
All 8 tour questions, with a free printable tour card (PDF).
Check a Winter Park community’s license
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.
Winter Park assisted living questions
Florida licenses 15 assisted living communities in Winter Park as of November 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. The table on this page shows each community's published price or a Lilisity estimate where we have one, and our free guide lists the questions to ask about cost.
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.