Visit us today and see why now is the right time to embrace senior living.
Welcome to Chartwell Oakville
Embrace a retirement lifestyle rooted in connection, comfort, and community—so you can enjoy your best years yet.
Chartwell Oakville is a well-established retirement community with a strong local reputation and dedicated, long-standing staff who truly get to know you. Our independent living lifestyle is tailored to your unique needs and preferences, offering the freedom to choose the support you want—on your terms, at your pace. With the flexibility to add or remove services as your needs evolve, our caring team ensures you can confidently age in place while enjoying the comfort, security, and personal attention you deserve.
An unbeatable Uptown Oakville location that invites you to live fully
Here, location means more than just convenience—it’s your connection to everything you enjoy. Our prime setting in Uptown Oakville places you in a thriving neighbourhood with a walkable blend of urban energy and residential charm. Just steps from your suite, you’ll find grocery stores, banks, restaurants, cafés, and retailers like Walmart, making errands and outings effortlessly easy. Prefer to drive? We offer heated underground parking. Want to leave the car behind? Our transportation services make staying active and connected a breeze.
A warm, social community where connection comes naturally
When you walk through our doors, you’ll feel the welcoming energy that defines life at Chartwell Oakville. Our residents often say it’s the people—both neighbours and staff—who make this place feel like home. Whether you're sharing laughs in the modern bistro over fresh coffee and baked treats, joining a lively fitness class, or catching up with friends in the spacious, sunlit lobby, there’s always something happening and someone to enjoy it with. Our open-concept design makes it easy to move throughout the home, adding to the uplifting ambiance and sense of community that sets us apart.
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 $3,845/month
At Chartwell Oakville, you’ll find some of the largest senior living suites in the region. Select from two different floor plans in our studios, all with kitchenettes, and from five floor plans in our one-bedroom suites, also with kitchenettes. Our two-bedroom suites are well-suited to couples or individuals in need of more space for furniture and belongings, with walk-in closet, storage space, and balcony. If you have a vehicle, we also offer optional underground parking.
Care Assist in Oakville at Chartwell Oakville
Wondering what types of care services are available at Chartwell Oakville? 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
At Chartwell Oakville, we offer three tempting, varied daily meals as part of your independent living lifestyle, helping you to enjoy your retirement focusing less on making meals and more on the things you want to do. Both our featured and à la carte menus are chock-full of fresh, wholesome, and seasonal ingredients, created with our residents’ palates in mind. Enjoy your meal restaurant-style in our warmly decorated dining room surrounded by friends.
Take a closer look at the lifestyle at Chartwell Oakville.
Activities and amenities
Come on in—the living is fine at Chartwell Oakville, where you can feel the vibrant, upbeat atmosphere the minute you step into our spacious, renovated lobby. You’ll see residents and staff in our soaring, light-filled lounge, chatting around the fireplace, perhaps discussing which activities are on offer for the day, or if there is an afternoon shopping outing. What looks interesting to you? Consider joining us for an art class or morning meditation, or a pizza-making demonstration. The walking club is off on a stroll, and the book club is discussing a classic spy thriller. The options are many and varied, and the choice is yours to do as much—or as little—as you please.
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.
Senior living in Oakville
Our unique blend of walkable residential neighbourhood and steps-away access to a large variety of major stores, restaurants, and almost any service you might need (including medical and dental clinics), is one reason residents are drawn to Chartwell Oakville. An established presence in the heart of family-friendly uptown Oakville, our residence is just down the street from Memorial Park, a beautiful slice of country in the city. Residents enjoy its butterfly garden, duck ponds, walking trails, foot bridge, and community garden. We are also minutes away from all major highways and state-of-the-art Oakville Trafalgar Memorial Hospital. The town’s historic and picturesque waterfront, with its boutiques, restaurants, galleries and festivals, is an easy bus or car ride to the south.
Things to do in Oakville
With its beautiful, vibrant lakefront, historic downtown, wealth of parks and walking trails, and a lively arts and cultural scene, Oakville offers many attractions and amenities perfect for a senior lifestyle. If you are a history buff, visit the beautiful Erchless Estate, home of Oakville’s founders, and now a fascinating museum. If you enjoy history and golfing, check out the Canadian Golf Hall of Fame, and consider making a reservation for brunch at the iconic Glen Abbey Golf Course. If you are a history lover and a walker, the Oakville Heritage Trail network has almost 60 km of walking paths dotted with information about the town’s past. If you are an arts lover, check the calendar at the Oakville Centre for the Performing Arts, home to the Oakville Ballet Company and Oakville Symphony Orchestra. If you are passionate about music, the Downtown Oakville Jazz Festival that runs every summer is definitely the place to be, where you can sit on a restaurant patio and take in free concerts too. If you love to eat, the Oakville Family Ribfest is a must-do, or in early spring, the Bronte Creek Maple Syrup Festival offers a sweet treat for everyone! If you enjoy a relaxing day out with endless possibilities, stroll the Bronte Harbour neighbourhood for its award-winning restaurants, sailing-off-into-the-sunset boat charters, and quaint boutiques, antique shops, and galleries.
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 Oakville?
Chartwell Oakville offers vibrant, independent retirement living in the heart of Uptown Oakville, where connection, comfort, and community come together to help you live your best retirement years.
Here’s what sets us apart:
- Warm, Long-Standing Staff: Our experienced team gets to know you personally, providing thoughtful, consistent support tailored to your evolving needs.
- Personalized Independent Living: Choose the services that suit you—on your terms, at your pace—for a flexible lifestyle that adapts with you.
- Vibrant Social Atmosphere: From lively events to casual chats in our bistro, meaningful connection is part of daily life.
- Spacious, Open-Concept Design: Enjoy easy navigation, sunlit common areas, and inviting spaces that make every day feel welcoming.
- Prime Location in Uptown Oakville: Steps from grocery stores, restaurants, cafés, and retailers like Walmart—plus easy access to transit and heated underground parking.
- Worry-Free Living: Say goodbye to chores and hello to comfort with services like flexible dining, weekly housekeeping and linen service, and transportation.
- Proudly Canadian: Trust in a Canadian-owned company known for its commitment to exceptional service and resident well-being.
At Chartwell Oakville, you’ll experience a retirement lifestyle rooted in freedom, connection, and peace of mind. [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 Oakville?
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 Oakville?
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.