Welcome to Chartwell Oak Park Terrace
Experience relaxed, single-level retirement living with cultural warmth in the heart of peaceful Windsor.
Chartwell Oak Park Terrace is a charming, bungalow-style retirement residence centered on active and independent senior living. We welcome you to explore the convenience of our accessible single-level layout, where you’ll find both our cozy one- and two-bedroom suites and bright, open-concept amenities. In addition to a warm and lively social atmosphere, retiring with us means you’ll have the comfort of an all-inclusive style of living and the peace of mind of personalized care services delivered by dedicated, long-standing staff.
Our residence is also known for its strong cultural roots, especially our Italian community spirit, which brings a sense of tradition, family, and connection to daily life.
A great location in Windsor
Located right beside the E.C. Row Expressway and airport, travelling to and from our residence is easy! Many of our residents have family both in Windsor and in the United States, which makes our location ideal as we’re nearby the border. Our retirement home is also surrounded by many parks, including Udine Park, Walker Homesite Park and many more. Just a few minutes away, you’ll find Devonshire Mall, where you can find everything you need: a variety of restaurants, shops, and other conveniences. And for your healthcare needs, Windsor Regional Hospital is within a short drive, along with a variety of nearby pharmacies.
Despite the convenience, our residence feels like a retreat—set in a quiet, park-like setting with leafy courtyards and walking paths that invite peaceful strolls and outdoor connection.
Worry-free services and support
Retirement living should be easy—and at Chartwell Oak Park Terrace, it is. You’ll enjoy three delicious, nutritious meals each day in our dining room, along with housekeeping, laundry, and linen services that let you relax and enjoy your time. Our all-inclusive services are designed for simplicity, comfort, and freedom. As your needs evolve, our personalized support adapts with you, so you can focus on what truly matters. Here, trusted care is delivered by familiar faces, as many of our team members have been part of the community for years, forming meaningful bonds with residents and families alike.
Flexible care and support
To ensure personalized support, our Care Assist program—an offering of à la carte wellness services and all-inclusive care packages—further provides you with the flexibility to add or remove services. This empowers you to create a customized care plan that meets your unique needs, preferences, and abilities so you can feel your best each day.
A selection of inviting suites
Starting from $4,815/month
A unique senior living residence in South Windsor, Chartwell Oak Park Terrace offers bungalow-style suites, all at garden level. You’ll find an independent living lifestyle in a selection of charming and well-priced studio, one-bedroom, and two-bedroom suites with kitchenettes. You’ll feel immediately at home in our residence with its seasonal décor, bright, open-concept spaces, and personalized mailboxes outside each resident’s door.
Care Assist in Windsor at Chartwell Oak Park Terrace
Wondering what types of care services are available at Chartwell Oak Park Terrace? Chartwell’s Care Assist Program is designed to help you or a loved one achieve the comfort and quality of life you desire in your retirement residence. We collaborate with you or your loved one to provide a customized care experience that reflects your unique healthcare needs, from light to moderate to heavy care. Visit our Care Assist page to explore our various à la carte services and care options.
The dining experience
There is no need to sacrifice quality, taste, or nutrition in your dining experience just because you are living in a retirement residence. Three delicious daily meals are part of our independent living lifestyle, helping you to enjoy your retirement focusing on the things you want to do. Both our featured and à la carte menus are chock-full of fresh, wholesome ingredients, carefully prepared, presented, and served. Enjoy your meal restaurant-style in our warm and traditional dining room next to the fireplace, or host family and friends in our private dining space.
Take a closer look at the lifestyle at Chartwell Oak Park Terrace.
Activities and amenities
The moment you step through the doors of Chartwell Oak Park Terrace, you’ll be greeted by the cheerful hum of conversation, the sound of laughter, and the inviting aroma of authentic Italian cuisine. You’ll find that life here is vibrant, engaging, and full of joy—whether it's a group outing to Devonshire Mall, a lively game of bocce in our yard, or peaceful moments spent nurturing herbs during gardening club. Many of our Italian residents also look forward to the tailored programs we offer that celebrate Italian tradition and connection. You might join a spirited game of Scopa or Briscola, participate in a cooking group perfecting classic Italian dishes, or engage with the wider community through our partnerships with local Italian clubs and cultural centres. Like you, our residents seek an active, fulfilling retirement on their own terms, and the place they call home has to offer them life-enriching activities and amenities; a true community that empowers their independence in a safe and supportive manner.
Stay Connected With Our Community
Catch a glimpse of our vibrant community in action. From celebrations and outings to everyday smiles, our social feed highlights the friendships and experiences that make Chartwell feel like home.
Retirement living in Windsor
Chartwell Oak Park Terrace is a pretty and peaceful enclave in South Windsor that’s quickly accessible to everything you need, and everywhere you want to go. With the E.C. Row Expressway, Windsor International Airport, and the Canada/U.S. border all just minutes away, our residence offers a secure and supportive home for our diverse group of residents, including seniors from Windsor’s Italian community. We are well-connected to our next-door neighbour, Fogolar Furlan Community Centre, established by Italian-Canadians over 60 years ago. Residents enjoy excellent shopping and restaurants at Devonshire Mall, and the Windsor Premium Outlets, both a short drive away. Several nearby medical and dental clinics, and Windsor Regional Hospital offer comprehensive healthcare. When residents aren’t relaxing in the garden, you may find them visiting beautiful Jackson Park, or taking a picnic to the Ojibway Prairie Provincial Nature Reserve.
Things to do in Windsor
Located on the banks of the Detroit River, Windsor is Canada’s southernmost city, a bustling urban hive with a five-kilometre-long waterfront park beginning at the historic Ambassador suspension bridge and continuing past the lovely Windsor Sculpture Park. While you’re there, you can also visit Dieppe Gardens, dedicated to Canadian veterans. What other activities, amenities, and events are on offer? Try your luck: Caesars Windsor Casino is also on the riverfront, and there are three other casinos in the region. Experience history: visit Willistead Manor, a Tudor-Jacobean-style manor with 36 rooms, set in a beautiful park. Commune with nature: the Ojibway Prairie Conservation Area is the place to walk, learn, and enjoy encounters with wildlife. Bird watchers in particular will love it. Attend a festival: the Windsor-Detroit International Freedom Festival offers exciting performances and huge fireworks displays. There’s more great music at the Bluesfest International Windsor too. Dine deliciously: for an excellent meal, head to Erie Street, known as Windsor’s “Little Italy.” And be artistic: visit the Art Gallery of Windsor with its collection of 4,000 pieces, or attend a show at the Windsor Symphony Orchestra or the Capitol Theatre.
Shopping for retirement homes?
There are many important factors to consider when trying to find the best retirement community for yourself or a loved one. Practical considerations like location, cost and the right support or care services for your unique needs, emotional considerations like how the residence made you feel and your interactions with staff, and so much more. Read our helpful guide today for questions to ask during a tour, topics to discuss with family, and how to make a decision you can feel confident in.
Frequently Asked Questions
What are the benefits of senior living at Chartwell Oak Park Terrace?
Chartwell Oak Park Terrace offers relaxed, one-level retirement living in a setting that’s both beautiful and culturally vibrant. Here’s what makes us different:
- Bungalow-style suites – Our single-level design provides easy, accessible living without stairs or elevators.
- Scenic, park-like grounds – Enjoy leafy courtyards, walking paths, and outdoor spaces that invite connection and calm.
- Warm, Italian cultural influence – Experience a strong sense of tradition, family, and community spirit.
- Convenient Windsor location – Near major highways, shopping, and amenities, our location offers peace and practicality.
- Proudly Canadian: Trust in a Canadian-owned company known for its commitment to exceptional service and resident well-being.
At Chartwell Oak Park Terrace, you’ll find comfort, connection, and a truly easygoing lifestyle that feels like home. [Book a Tour]
Will I lose my independence when I move to a retirement residence?
Not at all! Retirement living is designed to enhance your independence and freedom by relieving you of household maintenance and responsibilities. You’ll enjoy a variety of meal options and meal plans, life-enrichment activities, as well as the freedom and choice to come and go as you please. With retirement living, you are empowered to focus on the people and pursuits that matter most to you.
How much does it cost to live in Chartwell Oak Park Terrace?
Pricing details can be found in the 'suite plans' section of our website. It is essential to note that costs can vary depending on several factors, including the residence's location, the type of suite you choose, and the level of care services required. Given these variables, we believe it's crucial to offer personalized guidance to help you understand the pricing for residences in your desired area.
To ensure you have a clear understanding and to guide you through the pricing of our residence, our dedicated representatives are at your service. We strongly encourage you to give us a call at 1-855-461-0685, fill out our contact form, or book a tour for a more personalized discussion.
What types of suites are available in Chartwell Oak Park Terrace?
You can explore our suite layouts by navigating to the "Suite Plans & Pricing" section of our website. To see a suite you're interested in for yourself, we invite you to book a tour.
Can my family come and visit me?
At Chartwell, we understand the value of staying connected to family and friends. Your loved ones are always welcome to drop by at our residences! We also host events throughout the year to help you stay connected with them.
For more specific inquiries, including overnight stay policies, please reach out to your specific residence of interest.
Are pets allowed?
Yes! Our retirement residence is pet-friendly, and residents are responsible for the care of their loyal companions. We strongly encourage you to book a tour to ask about pet-specific restrictions.
Can I decorate my suite?
Yes! We want you to feel comfortable and at home in your new space. Feel free to personalize your suite with your favourite furniture, artwork, and cherished belongings that reflect your personality and style.