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Westchester of Winter Park

3.8 (59 reviews)

Winter Park, FL

Assisted Living and Skilled Nursing in Winter Park, with spaces to feel at home and support for your next chapter.

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About this community

Westchester of Winter Park is an assisted living community in Winter Park, Florida. The community describes its approach as combining housing, personalized support and healthcare tailored to residents’ needs, with an emphasis on independence and dignity. Care information includes help with daily activities and medication management, supported by trained nursing assistants and nurses. The community also says physicians are available on site. Its website identifies caregivers, nurses, activities coordinators and maintenance staff as members of the team.

Accommodation listings identify studio, one-bedroom and semi-private options. Meals are provided, with a professional chef and restaurant-style dining among the listed features. Other dining options include vegetarian meals, room service and a private dining room. The community says its dietary staff accommodates residents’ special dietary needs in meals. These dining features provide several listed settings and options, including a separate space for private meals.

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The listed healthcare services include assistance related to incontinence and diabetes, medication management and non-ambulatory care. Respite or short-term stays are also identified. Practical services on the amenity listing include housekeeping, laundry or dry-cleaning, and beautician services. Cable or satellite television and Wi-Fi or high-speed internet are listed as amenities. The available information names these supports and services but does not specify how an individual care plan is arranged.

Activities described by the community include fitness classes, yoga, arts and crafts, board games, game nights, group outings and team-building exercises. Additional activity listings name educational speakers, gardening, day trips and Wii bowling. The community says its activities department provides daily programs intended to encourage socialization. Together, the listed options include indoor pursuits, opportunities for movement and activities beyond the building.

Shared spaces include a library, game room, TV lounge and meeting room, along with indoor and outdoor common areas, a patio and an indoor atrium. A piano or organ, arts and crafts center and raised garden beds are also listed. These spaces and facilities correspond to different activities, from reading and games to creative projects and gardening. The community’s approach also emphasizes involvement by family and friends.

Faith-related programming listed includes on-site and off-site devotional activities, Catholic, Jewish and Protestant services, and visits by a chaplain or priest. Other amenities include a beauty salon and barber shop. Cats and dogs are listed as permitted, and English and Spanish are identified as spoken languages. Transportation information includes complimentary transportation and transportation at cost, as well as resident parking, uncovered parking and access convenient to public transit.

Starting at
$3,987/mo
Care options
2 available
Take a look
13 photos
Community reviews
59

Key amenities

Dining

Meal preparation and service

Pool & outdoor spaces

Garden

Fitness & wellness

Fitness programs

Housekeeping

Housekeeping and linen services

Transportation

Community operated transportation

Social activities

Community-sponsored activities

Staff & support

12-16 hour nursing

See all 40 amenities and services
  • 12-16 hour nursing
  • 24-hour call system
  • 24-hour supervision
  • Activities of daily living assistance
  • Air-conditioning
  • Assistance with bathing
  • Assistance with dressing
  • Assistance with transfers
  • Beauty salon
  • Cable
  • Community operated transportation
  • Community-sponsored activities
  • Computer center
  • Concierge services
  • Diabetes diet
  • Dining room
  • Fitness programs
  • Fitness room
  • Fully furnished
  • Gaming room
  • Garden
  • Housekeeping and linen services
  • Kitchenettes
  • Meal preparation and service
  • Medication management
  • Mental wellness program
  • Move-in coordination
  • Outdoor space
  • Planned day trips
  • Private bathrooms
  • Resident-run activities
  • Restaurant-style dining
  • Scheduled daily activities
  • Small library
  • Special dietary restrictions
  • Telephone
  • Transportation arrangement
  • Transportation arrangement (non-medical)
  • Wellness center
  • Wifi

Care options available

Assisted Living

Support with everyday routines and personal care in a community setting.

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Skilled Nursing

Nursing and rehabilitation services for people who need a higher level of care.

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“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.”
Community review · 2026

Pricing & residences

Monthly rates starting at

$3,987 / month

Rates and availability can change. Ask the community for a personalized quote and details about included services.

Listed monthly residence rates
Residence Monthly rate
Shared room $3,987
One bedroom $4,784
Studio $5,183

Resident & family reviews

3.8 · 59 reviews

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.

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.

I've been here at Westchester for about four months and I absolutely love it. Iliana Ramos the Administrator brought me over from regents nursing facility. She helped me with everything she is awesome. The food, the activities and the people are all wonderful. The food is always hot and good. The activities for the most part, keep you busy and are fun. And we have happy hour twice a month and an ice cream social. And celebrate all the holidays with food and drink. We play Bingo monday through friday. The staff is always caring and kind. Megan, the nurse administrator is always there to help…

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I've been here at Westchester for about four months and I absolutely love it. Iliana Ramos the Administrator brought me over from regents nursing facility. She helped me with everything she is awesome. The food, the activities and the people are all wonderful. The food is always hot and good. The activities for the most part, keep you busy and are fun. And we have happy hour twice a month and an ice cream social. And celebrate all the holidays with food and drink. We play Bingo monday through friday. The staff is always caring and kind. Megan, the nurse administrator is always there to help and solves your problems right away. My private room is very large and spacious. And I have decorated it to my liking and I love it just like I love it here!

More recent reviews

After having been here for almost 1/2 a year, I am relieved to know God placed me here. I have been in 3 other places prior to coming here, and Westchester is by far the best. The staff here, whether it be Daniel, the head administrator, or Iliana, the admissions director, will go above and beyond to satisfy their clients' needs as well as "wishes." Iliana, for example, has been known to give out her personal number at times, in case one of "us" is having any issues that couldn't be resolved completely during working hours. It's VERY RARE in my experiences thus far, to have someone do this in these kinds of establishments. Likewise, the D.O.N. Megan, continually strives to provide the best nursing staff required. She steadily upgrades the med tech's training, holding "review" sessions in order to maintain a satisfactory level of performance. I give Westchester 5 stars, and I recommend you come see for yourself. I'm sure Iliana will be glad to show you around, while answering all your questions and concerns.

I feel good here, everybody is nice I do not have complaint at all

Great facility, and even better personnel! Staff is excellent and very helpful and accommodating. Mom is very satisfied with the accommodations, and the care provided by the staff. Highly recommend!

My dad came to Westchester from nursing home and he feels right at home. He doesn’t miss a thing He loves his private room and the meals. Thanks to the admission lady , Iliana. She is being helpful.

Westchester is top notch. The staff are excellent and very loving. They are on top of making sure the residents get proper good care. I recommend Westchester to anyone that is looking for as assisted living. The place is always clean and well kept. I love that my mom is in the best hands.

What families highlight

  • Compassionate, attentive caregiving staff
  • Skilled nursing and medication support
  • Welcoming admissions and front-desk staff
  • Clean, well-maintained common areas and rooms
  • Large private apartments with ample storage

Highlights summarized from community reviews.

Location & neighborhood

558 N Semoran Blvd, Winter Park, FL 32792
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