Winchester Glen Retirement Community logo

THE COMFORT LIFE REPORT:Winchester Glen Retirement Community 

2501 Thoroughbred Street, Oshawa, Ontario, L1L 0P8
 (view map) | 15 reviews 

New Community Opened Mar, 2023

Lifestyle options:
Independent Living, Assisted Living
Guest stays available, Respite care available, Convalescent care, Private home-care allowed
Cost (from):
201 suites (1-bed, 2-bed, Studio)
265 residents

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Our Perspective

How we see Winchester Glen Retirement Community

From LEV Senior Living, creators of superior retirement communities around the Golden Horseshoe, Winchester Glen brings their expertise and experience in senior care to this North Oshawa neighbourhood. This is the right lifestyle change for seniors in the area. It will also appeal to both history and equestrian buffs with nods to the Windfields Farms legacy.

Through the beginning of the 2020’s, LEV Senior Living has garnered raves across its communities for its handling of coronavirus, demonstrating its diligence in both safety and care. Staff and administration across LEV communities are also singled out for praise, for their extraordinary commitment, and attention to seniors. Families and prospective residents of Winchester Glen will live in a community with a fulfilling lifestyle, where everyday is lived at full value.

The beautifully contemporary building design here is remarkable for its emphasis on natural lighting. The good life lived by residents here is spurred by onsite spa services, a salon, and full slate of daily activities. You can be as busy or as relaxed as you want to be. Seniors in this area of Oshawa will love the benefits of living in a community with others their own age, many from the area, who share both past experiences and present circumstances. It’s the right place to be.

Community’s Perspective

How Winchester Glen Retirement Community sees itself

Who are you as a community?

After years of working hard and planning for your retirement, you deserve to spend your golden years in a place you feel proud to call home. Winchester Glen offers a variety of suites in different sizes and styles; we can help you find the perfect new home.

Large and comfortable studios, 1-bedroom and 2-bedroom suites have plenty of room for your treasured belongings.  Once you decorate with your own furniture and add your personal touches, your home at Winchester Glen Retirement Community will offer an enjoyable, comfortable, and active lifestyle where you can be as busy or relaxed as you want to be.

Now picture yourself at home at Winchester Glen Retirement Community enjoying the privacy of your independent suite with all the amenities and services you expect and deserve at your doorstep. Imagine a place where your neighbours become your friends; where at any time, you can enjoy a laugh over a coffee in the Bistro, indulge in a night of live entertainment, or join in the fun at one of the numerous activities and daily recreational programs Winchester Glen has to offer! But don’t just take our word it, come and experience life at the Glen…it might be just what you need!

What do you do differently or uniquely well?

Winchester Glen offers custom pricing tailored to your personal needs, full kitchens and in suite laundry for those who want apartment style accommodations, and flexible meal plans so that you can spend your time doing what you are passionate about.

What supports do you offer residents as they adjust to life there?

New residents are introduced to like-minded residents in one-on-one settings and through welcome events. Each department manager will meet you in the to understand your needs, suggest tailored services and make you feel like part of the community. Staff are present 24/7 to make sure that you feel at home!

How are residents supported if their needs change?

Winchester Glen Retirement Community has not responded to this question yet.

Under what conditions would you advise someone against choosing your community?

Winchester Glen Retirement Community has not responded to this question yet.

What might residents find surprising about your community?

You don’t have to give up your full kitchen if you don’t want to! Independent suites have a full stove and dishwasher if you still enjoy cooking and entertaining. You are welcome to join us in the Dining Room or Bistro to indulge in a chef prepared meal if you don’t feel like preparing a meal some days!

How will your community change in the next five years?

Winchester Glen Retirement Community has not responded to this question yet.

What five facts about your community should people know?

1) We have exceptional amenity space and common areas. Our bright and beautiful corridors are accessible and roomy.
2) We are close to essentials, grocery store, Costco, restaurants, parks, walking/hiking trails and much more! We are close to major routes so that families out of town can easily pop by to visit you.
3) You can build meaningful friendships with neighbors that share the same or similar interests. Our activity calendar with surely keep you busy with excursions, trips, public speakers and much more.
4) We have a flexible meal option, be part of the plan or cook in your own kitchen!
5) We are located on E.P. Taylor's historic Windfield Farms. It holds a significant place in the history of horse racing.

Insider Perspectives

Reviews of Winchester Glen Retirement Community

What residents and their loved ones say about Winchester Glen Retirement Community in reviews.

Bill Baker, family member

"I moved my 96 year old father and 90 year old mother here from Kingston last March and it was the best thing we could have done. The building is laid out beautifully. Both mom and dad are happy here. The staff are like friends to them. Having nursing staff here makes them feel safe and secure. The food is terrific and the activities here help keep them happy. I highly recommend Winchester Glen."

David Love, family member

"Visiting a parent in a retirement home when you live out of province was made so, so easy by the warm hospitality of the Winchester Team. I stayed in a great guest suite so was just a short walk down the hall to see my Dad. The new building feels like a resort, but more importantly, it's good to know your parent is in the right place."

Peggy Bourne, family member

"I researched and visited several places for my brother and the minute that Emily had finished our tour I wanted to sign him up. When we took him for his tour he immediately felt welcome. I can’t say enough about the staff, they are all so caring and friendly. When my brother needed medical assistance the staff was right there for him. Emily was so helpful answering all of our questions at every step along the way. Sara is amazing, she has made sure that my brother has been involved in social a..."

Read all reviews

Testimonials and Stories

  • From One Senior To Another

    Hi, My name is Ann and I am a resident at Winchester Glen Retirement Community, I would like to share my experience on Retirement living with you from one Senior to another.

    “Retirement”– it’s an easy word to say and spell but when “Home” is added to it then it becomes something totally different.

    Retirement Home! ME ?! NEVER !!!

    I refused to even think about it. My husband and I had lived our entire lives in our home on a nice piece of property where we had our garden, patio, big back yard, wildlife and more. Contemplating moving after his passing was something I just brushed away.

    Leaving my memories, my independence, and MY home – No thanks! No Retirement Home for me! I was going to keep what I had.

    Then Covid hit, while I was having some health issues. My kids wanted me to consider looking at Winchester Glen. I looked (not too hard at first) then as time went on and I went back to look more, it didn’t seem that bad. I took the plunge and moved in May.

    It’s coming up to 5 months and I cannot tell you how it has changed my life for the better. This is a beautiful new home with a wide variety of modern suites, phenomenal staff, great activities and the food is exceptional!

    I have been fortunate enough to meet quite a few seniors while they are taking tours of my home and I would like to point out some common questions/concerns that usually arise:

    1) Is it an old age home? Well, it is for seniors, but I can assure you that we are active and enjoying life here! We have a theatre where we gather to watch sporting events and movies. There is a pub located on the 2nd floor where we enjoy cocktails while listening to live entertainment, common lounge where we play cards, shoot a game of pool, work on a jigsaw puzzle, go to our fitness room, hobby room, outdoor patio or just sit and chat.

    2) How difficult was the transition? Any change is hard and as we age, change is harder. Some of us are making the change without our spouse, some are relocating from a different part of the province to be closer to their family and some are moving for health and safety reasons. The decision to move was hard… but once it was made, I found everything else quite easy! I settled in quickly and feel very at home here. And Hey! I have 5 kids, so the actual move was conducted with free child labour… available for rent if needed.

    3) Is it affordable? For me personally it’s comparable to having my home. Here, all utilities are included, phone, cable, internet, and an emergency pendant. There are no maintenance fees, no utility fees, no property taxes - one bill, no stress!

    4) The area seems quite busy. Most of Durham Region is growing and yes, it is a densely populated area, however, I am happy with the closeness of everything I would need. ie. Costco, banks, restaurants, grocery stores, pet food, pharmacy and more!

    These are all a short 2–3 minute drive away. Let’s face it, most retirement homes are built in areas like this that cater to the needs of Seniors, so they don’t need to be driving on the busy roads for long.

    5) How was it making new friends? I have been very fortunate to meet some wonderful new friends that had the same fear and concerns that I had. Everyone is very kind and caring and you feel like they have been your friends and neighbours for years.

    For anyone considering Retirement Living, I can honestly say this transition has improved my quality of life and I wish I had moved sooner. Come for a tour here at Winchester, you may be pleasantly surprised!

    You can even ask for me by name!



Lifestyle options

Independent Living (definition)
Cost from $3,800

Independent Living is a good option for residents seeking the benefits of living in a senior-friendly community while still enjoying all the choices of living independently. Our flexible pricing enables residents to add and remove services such as meal plans, housekeeping and care services whenever they like. Independent Living offers 1-bedroom and 2-bedroom private suites in a variety of styles in the Elmcroft South section of the building. All suites are equipped with full kitchens and in-suite laundry. All residents in Elmcroft South enjoy full access to all amenities, recreation activities and on-site entertainment.


  • Designated dining area
  • Meals (Extra fee)
  • Meals credits (Extra fee)
  • Daily tidy (Extra fee)
  • Housekeeping (Extra fee)
  • Medication administration (Extra fee)

Assistance with

  • Bathing (Extra fee)

Assisted Living (definition)
Cost from $3,800

Independent Supported Living is ideal for seniors looking for a full-service retirement experience. Our all-inclusive pricing lets you rest easy knowing that the tiresome chores of cooking, housekeeping and linen laundry are taken care of for you. Residents in Independent Supported Living also have the reassurance of having the support of our care staff for medication administration and 24-hour emergency assistance, if needed. Additional care services are available as needs change over time. Independent Supported Living is best suited for seniors who may need some support, but do not require intensive medical and nursing care provided in long-term care facilities. Independent Support Living offers studios, 1-bedroom and 2-bedroom private suites in a variety of styles in the Parkwood North building. All suites include a kitchenette with a fridge/freezer, a sink, cupboards & counterspace. Complimentary laundry facilities are located on each floor. All residents who opt for Independent Supported Living enjoy full access to all amenities, recreation activities and on-site entertainment.


  • Designated dining area
  • Cancer care (Extra fee)
  • Diabetes (Extra fee)
  • Dialysis (Extra fee)
  • Multiple Sclerosis (Extra fee)
  • Stroke care
  • Meals (2x/day)
  • Meals credits (Extra fee)
  • Daily tidy (Extra fee)
  • Housekeeping (1x/week)
  • Incontinence care (Extra fee)
  • Medication administration
  • Resident Reminders

Assistance with

  • Bathing (Extra fee)
  • Dressing (Extra fee)
  • Transfers (Extra fee)


Type Size
(sq ft)
Lifestyle CostCompanion fee Includes Contact
1-bed 635 - 840 $3,800 - $4,300 (Rent) +$250 per month
  • Cable TV in room (included)
  • Call Bell System
  • Kitchen
  • Patio/Balcony
  • Personal phone number in room (included)
2-bed 969 - 1152 $4,400 - $4,800 (Rent) +$250 per month
  • Cable TV in room (included)
  • Call Bell System
  • Kitchen
  • Patio/Balcony
  • Personal phone number in room (included)
Studio 366 - 463 $3,700 - $3,900 (Rent) +$600 per month
  • Cable TV in room (included)
  • Call Bell System
  • Kitchenette
  • Personal phone number in room (included)
1-bed 549 - 807 $4,100 - $4,700 (Rent) +$600 per month
  • Cable TV in room (included)
  • Call Bell System
  • Kitchenette
  • Patio/Balcony
  • Personal phone number in room (included)
2-bed 786 - 899 $4,700 - $4,900 (Rent) +$600 per month
  • Cable TV in room (included)
  • Call Bell System
  • Kitchenette
  • Patio/Balcony
  • Type: 1-bed
  • Ownership: Rent
  • Cost: $3,800 - $4,300
  • Size: 635sq/ft
  • Companion fee: +$250
  • Details:
    • Cable TV in room (included)
    • Call Bell System
    • Kitchen
    • Patio/Balcony
    • Personal phone number in room (included)
  • Contact: email

  • Type: 2-bed
  • Ownership: Rent
  • Cost: $4,400 - $4,800
  • Size: 969sq/ft
  • Companion fee: +$250
  • Details:
    • Cable TV in room (included)
    • Call Bell System
    • Kitchen
    • Patio/Balcony
    • Personal phone number in room (included)
  • Contact: email

  • Type: Studio
  • Ownership: Rent
  • Cost: $3,700 - $3,900
  • Size: 366sq/ft
  • Companion fee: +$600
  • Details:
    • Cable TV in room (included)
    • Call Bell System
    • Kitchenette
    • Personal phone number in room (included)
  • Contact: email

  • Type: 1-bed
  • Ownership: Rent
  • Cost: $4,100 - $4,700
  • Size: 549sq/ft
  • Companion fee: +$600
  • Details:
    • Cable TV in room (included)
    • Call Bell System
    • Kitchenette
    • Patio/Balcony
    • Personal phone number in room (included)
  • Contact: email

  • Type: 2-bed
  • Ownership: Rent
  • Cost: $4,700 - $4,900
  • Size: 786sq/ft
  • Companion fee: +$600
  • Details:
    • Cable TV in room (included)
    • Call Bell System
    • Kitchenette
    • Patio/Balcony
  • Contact: email


When you live at Winchester Glen, you can enjoy gourmet meals every single day without ever having to worry about grocery shopping, cooking, and washing dishes. Our chef-prepared meals are made with the freshest ingredients and served by courteous staff in our elegant dining room. Every meal will be well-balanced and as delicious as it is nutritious. Our dining team will prepare varied entrees, hearty soups, a variety of fresh salads and vegetables. For those with a sweet tooth, our tempting desserts will be hard to resist. Mealtimes are flexible and menu choices will be available at each meal to cater to your tastes. Special diets will be accommodated whenever possible. We offer flexible meal-plan options to suit everyone’s needs. Whether you join us every day, once a week or anytime you need a break from cooking, our friendly dining staff will be ready to look after you when you arrive. Guests are always welcome, and arrangements can be made for family and friends to join anytime. You can even reserve our private dining area for special occasions and family celebrations. Once you invite your family to join, they will be asking when they can come back next. For snacks and lighter meal options, you can visit our Bistro Café at your convenience any time of the day. Do you enjoy cooking? If yes, be sure to choose a suite in Elmcroft South – the Independent Living section of the community. With full kitchens in every suite, you can prepare your own meals at your convenience but still have the option to join us for a meal in the dining whenever you choose.

Meal service : Bar, Bistro: (daytime), Pub, Room Service (extra fee), Tray service in suite (extra fee)

Seating type : Open seating

Special diets : Diabetic, Kosher style, Lactose free, Low sodium, Vegetarian

Amenities & Services

Residence Amenities & Services

24-hr concierge
Arts and crafts
Community Garden
Emergency call system (pendent)
Fitness Studio
Games Room
Hobby kitchen
Laundry machines
Mail box
Movie theatre
On-site General Store
Onsite foot care
Parking (indoor)
Parking (outdoor)
Pet friendly
Private bus for outings, regular trips
Private dining room for family/friends
Recreation facilities onsite
Spa Services
Spa/Beauty Salon
Storage lockers
Walking Path
Wellness Center
Wheelchair (electric)
Wheelchair (scooter)
Wheelchair Accessible

Programs & Activities

At Winchester Glen, you will have the choice to spend your days however you like. Each day, there will be an array of activities waiting for you, just outside your front door and you will be encouraged to do whatever makes you smile! Staying socially, physically and mentally active as we age is key to a healthy and happy lifestyle. At Winchester Glen, you will have plenty of opportunities to engage in activities with other residents that feed your mind, body & spirit. Our Recreation Manager will soon get to know you and your interests and will keep the recreation calendar full of activities you will be sure to love – both on-site at Winchester Glen and planned excursions to nearby attractions.

Arts and Crafts
Assisted Walks/Trails
Bible Classes
Billiards/Pool Tables
Bocce Ball
Brain Fitness
Continued education
Day Trips
Exercise Program
Horseshoe Pits
Movie Nights
Religious & Holiday Services
Table Tennis
Weekly Shopping Trips & Excursions

Staff & Care

General Manager's Message
Jennifer Stevens

For as long as I can remember I have always been passionate about working with seniors and find it very personally rewarding. Some of my previous experience has been in a Therapeutic Recreation Management role in LTC for over 20 years, and most recently as a General Manager in the Retirement sector for the past 6 years. I am very excited to be apart of the new Winchester Glen Community, not only to be able to engage and build relationships with residents, staff, and families, but to be able to welcome residents into this beautiful home with all the amenities it has to offer.


Medical and other support staff
Registered Practical Nurses8 hrs/day
Personal Support Workers24 hrs/day
Doctorvisiting 1x/week
Health & Wellness Teamvisiting 5x/week
Massage Therapiston call
Geriatric Pharmacistvisiting 1x/week
Mobility Specialiston call
Foot care specialistvisiting 2x/month
Dentistvisiting 1x/month
Physiotherapistvisiting 3x/week

Number of care staff:

  • Daytime: 5
  • Weekends: 3
  • Nights: 3

Care services

Care options available:

  • Guest stays available (cost from $120)
  • Respite care available (cost from $135)
  • Convalescent care (cost from $135)
  • Private home-care allowed

Health Services:

  • Catheter care(with special assistance)
  • Medication charted by electronic pen(with special assistance)
  • Medication charted by exception(with special assistance)
  • Ostomy care(with special assistance)
  • Oxygen assistance(with special assistance)
  • Physically challenged residents(with special assistance)
  • Vitals monitoring(with special assistance)

Move-in requirements

• Chest x-ray
• Medical form completed by family doctor
• TB test required

COVID-19 Information

Currently accepting move-ins. Request suite details.


Accreditation & Associations

Social Feed



Our central location means you will have easy access to the many of the attractions Oshawa has to offer. For instance, you may wish to visit historic sites such as the Parkwood Estate, engage with art & culture at the Robert McLaughlin Gallery or enjoy a variety of other attractions including the Oshawa Valley Botanical Gardens. For those who like to shop, Oshawa Centre is the largest retail mall in the region and will be just a short drive from Winchester Glen. We also have a new plaza within a short walking distance directly north of the Community ! It too offers a wide variety of stores to choose from.

Winchester Glen Retirement is located at 2501 Thoroughbred Street, Oshawa, Ontario, L1L 0P8.

What's nearby:

Brooklin Medical Center
Oshawa Senior Community Centre
Riocan Windfields
White Feather Farms
Winchester Golf Course
Great Blue Heron Casino

Compare Winchester Glen Retirement Community with nearby communities

Compare with Lifestyle options Location Distance
Harmony Hill Retirement CommunityIndependent Living, Assisted LivingOshawa, Ontario 4.67km
Livita Centennial Retirement ResidenceIndependent Living, Assisted LivingOshawa, Ontario 5.16km
Take It Easy Care Inc. Independent Living, Assisted LivingOshawa, Ontario 6.54km
The Village of Taunton MillsIndependent Living, Assisted LivingWhitby, Ontario 6.85km
Amica WhitbyIndependent Living, Assisted LivingWhitby, Ontario 6.94km

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Winchester Glen Retirement Community

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