Welcome to Chartwell Montgomery Village
Discover stylish apartments, lively social experiences and stunning farmland views at Orangeville’s premier retirement residence.
Chartwell Montgomery Village is a premier retirement community offering seniors’ apartments designed for active older adults in Orangeville who seek a vibrant lifestyle, supportive services, and the freedom to live on their own terms. Our independent living residence—reflecting the charm of Victorian architecture found in downtown Orangeville—offers more than just beautiful design. You’ll find state-of-the-art amenities like a therapeutic indoor pool, a putting green, and a welcoming bar and lounge, all thoughtfully designed to support your health, happiness, and sense of community. And yes—we’re pet-friendly, so your four-legged companions are welcome too!
Find that at-home feeling
Our suites and seniors’ apartments are warm, spacious, and well-appointed, many with views of surrounding farmland and lush green spaces that invite daily connection with nature. But what truly makes us a home? It’s the combination of our exceptional amenities, vibrant and inclusive atmosphere, and enriching variety of leisure and social opportunities—including regular events and outings. Most importantly, it’s our friendly, dedicated staff who take the time to build real relationships with you, making each day feel comfortable and full of possibility.
Explore our selection of brand-new apartments!
Our 122 brand-new seniors’ apartments at our sought-after retirement community feature full kitchens equipped with a fridge, stove, oven and dishwasher, as well as in-suite laundry. Prepare your own meals in the privacy of your suite, or enjoy delicious chef-prepared meals and conversation with others by taking advantage of our flexible meal packages in the social dining room. The choice is yours, every day.
To complement your lifestyle, we’ve also introduced new amenities: a bright, social dining room, theatre, multi-purpose and fitness rooms, and secure scooter storage—all created with comfort, activity, and community in mind.
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.
Care Assist in Orangeville at Chartwell Montgomery Village
Wondering what types of care services are available at Chartwell Montgomery Village? 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
Chartwell Montgomery Village offers a premier senior lifestyle with a dining experience sure to exceed your expectations. Imagine not having to think about grocery shopping, prepping, and cooking or cleaning up at mealtimes if you don’t feel like it, knowing that your only decision is whether to order from the daily featured menu or the multi-choice à la carte menu.
Residents in Chartwell Montgomery Village’s main residence receive three delicious and nourishing daily meals in their inclusive monthly fee, while seniors in our new seniors’ apartments have the option to choose up to three meals per day to add to their package. Regardless of your choice, you’ll enjoy chef-prepared fare made from fresh, wholesome ingredients, sourced locally whenever possible from our supplier, in menus showcasing the bounty of the season. Served by friendly staff in our gracious dining room, each meal offers a very satisfying dining experience.
Take a closer look at the lifestyle at Chartwell Montgomery Village.
Activities and amenities
Chartwell Montgomery Village was designed to reflect gracious retirement living and thus offers an abundance of unique amenities and activities for seniors. This is a place for vibrant, active living, where you can dine with friends in our dining room, practice your swing on our putting green, or take a luxurious dip in our therapy pool. And when you come in from walking your pup in our beautiful surrounding green space, you can always clean their paws in our on-site dog wash too. Here you’ll be able to live your retirement exactly as you please, with an abundance of activities to choose from.
A selection of inviting suites
PROMO starting from $2,999/month
Whether you choose one of our well-appointed studio, one-bedroom, one-bedroom-plus-den, or two-bedroom suites—all featuring kitchenettes—or a newly-built studio, one-bedroom, or two-bedroom seniors’ apartment with full kitchen, we have a large variety of layouts to match your needs, preferences, and budget.
Senior living in Orangeville
You’ll find Chartwell Montgomery Village in suburban northwest Orangeville, nestled amongst acres of woodlands and fields, yet conveniently close to major retailers, grocery stores, banks, and healthcare clinics, including Headwaters Health Care Hospital, just 10 minutes away. Residents enjoy shopping at Sobey’s, No Frills, Walmart SuperCentre, Winners, and Michaels, as well as dining at popular chain restaurants, also conveniently nearby. Orangeville’s historic and charming downtown is also minutes away by car or transit. Right across the street, residents appreciate even more green space at Bravery Park, as well as the easy walk to all of the amenities—including library—at the Alder Street Community Centre.
Just over an hour from Toronto, our residence is easily accessible to Highway 400 and major arterial roads.
Things to do in Orangeville
Orangeville has much to offer for seniors who enjoy an established small-town ambience with urban amenities, surrounded by tranquil green spaces and parkland. Orangeville’s historic downtown is a great place to start—the first weekend in June, the award-winning Orangeville Blues & Jazz Festival takes the stage with over 90 acts. There’s more entertainment to be had at a performance by Theatre Orangeville, a professional company housed in the historic Opera House. You’ll find even more talent in regular performances by the Orangeville Music Theatre, Community Band, and Show Chorus. While you’re still downtown, enjoy the unique shops, studios, and galleries that line Broadway. Colourful public art sculptures are a must-see, with the beauty of many local trees preserved in more than 40 incredible sculptures. Stop into one of the many locally owned shops, and the restaurant scene is definitely worth exploring. For fresh-from-the-field fare, the year-round farmer’s market is another satisfying delight. Orangeville loves a good food festival too—mark your calendars for the Rotary Ribfest in July and Taste of Orangeville in August. The fun continues long past summer in the downtown core with “Boo on Broadway” in October, tree lighting and Santa Claus Parade in November.
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 Montgomery Village?
Chartwell Montgomery Village offers vibrant, independent senior living in the heart of Orangeville, where natural beauty, superb on-site amenities, and a warm community atmosphere create a truly fulfilling lifestyle.
Here’s what sets us apart:
- Brand-New Seniors’ Apartments: Choose from thoughtfully designed apartments featuring full kitchens, in-suite laundry, and private balconies or patios—perfect for those who value independence and comfort.
- Lush Natural Surroundings: Nestled among peaceful green spaces with scenic views of surrounding farmland, our setting offers daily connection to nature.
- Pet-Friendly Living: Furry companions are part of the family too—our community welcomes pets!
- State-of-the-Art Amenities: Enjoy access to a therapeutic indoor pool, putting green, bar and lounge, theatre, fitness room, and more—designed to support wellness, relaxation, and fun.
- Flexible Dining Options: Prepare meals in your own suite or savour chef-prepared dishes with friends in our welcoming social dining room. The choice is always yours.
- Engaging Lifestyle: Participate in lively social activities, hobby groups, and enriching outings that help you stay active and connected.
- Dedicated, Caring Staff: Our friendly team is committed to your well-being, building real relationships to make each day feel safe, comfortable, and meaningful.
- Inspired by Local Charm: Our residence reflects the timeless Victorian architecture of downtown Orangeville—adding beauty and character to everyday living.
At Chartwell Montgomery Village, you’ll find the perfect blend of independence, nature, and community. [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 Montgomery Village?
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 Montgomery Village?
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.