Carmen Estrada
Aug 2026
I have my brother in Westchester, was the best desicition we did as a family. He love the place, good environment and food. I recommended it to everyone.
Westchester of Winter Park
558 North Semoran Blvd4.1(66 ratings)· Winter Park average: 4.4
Own this community? Update your listing · Marketing for operators
1 / 6Quick Facts
- Total units
- 121
- Licensed capacity
- 121 residents
- Room layout
- Private rooms include a kitchenette area
- Medical access
- On-site physicians provide medical care
- Regulatory history
- State deficiencies and fines reported in 2025
Florida AHCA
What Families Think
An automated summary of family reviews and public information. Not verified by MyLivingChoice; confirm services, staffing and pricing with the community.
Reviews of Westchester of Winter Park are sharply split: many families and residents praise the spacious private rooms, food, activities, and especially the current administration team (Daniel, Megan, Iliana), describing a strong turnaround under new management. However, a substantial minority describe serious lapses in care, including slow response to call buttons, missed medication, and laundry problems, particularly tied to earlier periods of high staff/administrator turnover.
What reviewers praise
- Spacious private rooms with kitchenette and large closets
- Repeatedly praised admissions and nursing leadership (Daniel, Megan, Iliana)
- On-site physicians and home health therapists
- Varied activities: billiards, bingo, happy hours, ice cream socials
- Many reviewers note noticeable improvement under recent management
- Residents describe good food with meal choices
What reviewers flag
- Multiple reports of slow call-button response, sometimes hours
- Several reviewers cite understaffing affecting dining and daily care
- Repeated complaints about lost or unwashed laundry
- One report cites state-documented deficiencies and fines in 2025
- Frequent turnover in administrators noted as disruptive by several reviewers
AI-generated from reviews and community data.
Westchester of Winter Park is a senior living community in Winter Park, Florida offering Assisted Living. Amenities include Restaurant style Dining Room, Gathering / Activity Spaces and Social Activities. Families rate it 4.1 out of 5 across 66 reviews.
About Westchester of Winter Park
Westchester of Winter Park is an assisted living residence in Winter Park, Florida that provides personalized care and support for older adults seeking an enriched lifestyle with community and companionship.
The community offers trained nursing assistants and on-site physicians to provide comprehensive healthcare services, including medication management and daily assistance tailored to individual needs. Care is delivered by a team of experienced caregivers, nurses, activities coordinators, and maintenance personnel dedicated to residents' well-being and comfort.
Residents enjoy a diverse range of recreational and social activities designed to foster engagement and connection. These include fitness classes, yoga sessions, arts and crafts, game nights, board games, and group outings. The facility features amenities such as a game room, billiards room, library, and piano, as well as on-site home health therapists.
The community emphasizes creating a supportive environment where residents feel valued and respected. Staff members are noted for their attentiveness to residents' needs and their compassionate approach to care, fostering a vibrant community atmosphere.
Types of Care at Westchester of Winter Park
Assisted Living
Amenities
Room Amenities
- Cable or Satellite TV
- Emergency Call System
- Private Bathroom
- Private Rooms
- Wheelchair Accessible
Meals & Dining
- Dietary Accommodations (Gluten-Free, Low / No Sodium, No Sugar, Vegan)
- Restaurant style Dining Room
Community Amenities
- 24-Hour Staff
- Gathering / Activity Spaces
- Housekeeping
- Laundry Service
- Medication Management
- On-Site Nurse (RN)
- Salon / Barber
Activities
- Arts and Crafts
- Birthday / Holiday Parties
- Day Trips and Outings
- Games
- Social Activities
Need help deciding?
Tell us what you're looking for and we'll match you with communities that fit. Free for families.
Help Me ChooseReviews of Westchester of Winter Park
4.1overall · 66 ratings combined
4.1★ on Google (66)
Marta
Aug 2026
I like the place because is big snd bright and they have a bilingual personal. I like the staff. I think.this is a good place to bring your parents.
Edwin Mercado-Rivera
Jun 2026
I have been 20 days at this facility and my experience has been excellent especially the rapport that I have developed with the Admissions Officer ileana Ramos. She was instrumental in my decision to move to this facility and continues to be my contact person for all my needs. Thank you Ileana.
Sue Crosby
May 2026
I am POA for a friend of mine who moved into Westchester a few months ago. The positive change from where he was is wonderful! His room is spacious and he feels like himself again. The staff is very knowledgeable and friendly. The administrator, Daniel, truly cares about the residents and always keeps me posted . I highly recommend Westchester.
Ana del Valle
May 2026
Desde que me mude a westchester me he sentido tranquila, mi cuarto es suficientemente grande para poner todas mis pertenencias. La comida es muy buena y sierven buenas porciones.
Frequently Asked Questions
What types of care does Westchester of Winter Park offer?
Westchester of Winter Park offers Assisted Living.
Where is Westchester of Winter Park located?
Westchester of Winter Park is located at 558 North Semoran Blvd in Winter Park, Florida.
What do families say about Westchester of Winter Park?
Westchester of Winter Park carries a 4.1 out of 5 rating from 66 Google reviews. Reviews of Westchester of Winter Park are sharply split: many families and residents praise the spacious private rooms, food, activities, and especially the current administration team (Daniel, Megan, Iliana), describing a strong turnaround under new management. Reviews on MyLivingChoice come from families who confirmed a connection to the community and appear with the reviewer's first name and last initial.
How can families visit Westchester of Winter Park?
Submit the Request Information form on this page, or contact Westchester of Winter Park directly, to arrange a tour. Sharing your timeline and care needs up front helps the community prepare for your visit.
Work at Westchester of Winter Park? Claim this listing to update photos, pricing, and details. It's free.
Nearby Communities
Other senior living options within 25 miles of Winter Park.
Allegro Senior Living Winter Park, FL
Winter Park, Florida0 mi
4.7(110)
Assisted LivingIndependent LivingMemory Care
Regents Park Health Care Center
Winter Park, Florida0 mi
4.5(235)
Skilled Nursing / Long Term Care
The Mayflower at Winter Park
Winter Park, Florida0 mi
4.5(172)
Medicare home health · 3.0★
Westminster Winter Park
Winter Park, Florida0 mi
4.2(90)
Skilled Nursing / Long Term Care
Aiden Springs Assisted Living
Winter Park, Florida0 mi
3(2)
Assisted Living
Winter Park Care and Rehabilitation Center
Winter Park, Florida0 mi
3.8(116)
Skilled Nursing / Long Term Care
Prefer to stay home?
Home care agencies serving Winter Park bring help to the house: daily living, companionship, and respite for family caregivers.
Griswold Care Pairing for Greater Orlando
Winter Park, Florida4.3 mi
5(61)
Home care · no referral needed
Home Instead Orlando
Orlando, Florida3.4 mi
4.9(291)
Home care · no referral needed
Home Instead, Home Care Services of Seminole County
Altamonte Springs, Florida7.5 mi
4.9(42)
Home care · no referral needed