May 11, 2023 | Downsizing
Top FAQs About Downsizing in Oakville

Oakville is known as a picturesque little city with luxurious homes where many affluent professionals and families reside. It may not seem like the obvious choice when downsizing, but there are many reasons to consider it. For one, you’ll enjoy access to the best of everything, including fine dining, vibrant shopping opportunities, and a thriving arts and entertainment community. Perhaps best of all, everywhere you go is safe, peaceful and scenic. Where do you start if you decide to make Oakville your new forever home? In this post, I’ll answer some of the most pressing questions you may have about downsizing in Oakville.
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When is the best time to downsize?
Should you downsize early to take advantage of a hot real estate market? Or should you wait until after you retire? These are some of the toughest questions to answer because everyone is so different. The decision of when to downsize depends on your financial situation and your ability and desire to take care of your current home.
- If a smaller house with less work sounds like paradise, now could be the perfect time.
- If the thought of leaving your beloved family home makes you want to burst into tears, you may not be ready yet.
The right answer is whenever it is right for you and when you are doing it for your own reasons, not because someone else thinks you should. Downsizing can and should be a joyful, exciting time, not something you’re pressured into before you’re ready.
Downsizing in the current market can be challenging. The following posts will help you make well-informed decisions:
- Should You Downsize to Rent?
- Should You Appoint Power of Attorney Now?
- How Can I Maximize the Sale of My House When Downsizing?
Aren’t the houses in Oakville too big for downsizers?
Oakville is home to some of the wealthiest people in Canada. As such, many of its residences are large, luxurious properties that require multiple staff members to maintain. This may not sound ideal for you, especially when you’re looking to simplify your life. However, these massive estates comprise only a small portion of the real estate opportunities in Oakville. You’ll find nearly anything you want with a little help from a local real estate agent.
- Do you prefer a detached house with a backyard for entertaining that is smaller and less work than what you currently have? Perhaps a well-maintained bungalow, such as you’d find in Bronte, will suit your needs perfectly.
- Would you rather have even more freedom and next to no maintenance to worry about? A cozy but modern condo or townhouse in Central might be what you’re looking for.
Oakville’s real estate landscape offers a multitude of housing options, including a vibrant rental market if you’d prefer not to buy a house at all.
What are the best neighbourhoods for retirees?
One of the greatest things about Oakville is there is no such thing as a “bad” neighbourhood. Some areas are more modest than others, but everywhere is clean and safe. Choosing your community simply comes down to your financial resources and the lifestyle you want to enjoy. For example:
- Living in Central means you’re close to the downtown core and all of the conveniences that go along with it. You can spend your afternoons exploring the art galleries and museums and visiting the unique little shops in between. And even with all the hustle and bustle, you’ll find many peaceful green spaces where you can relax and commune with nature.
- Clearview is a more family-friendly community, with plenty of parks and an interconnected trail system. If you love staying active in the great outdoors, this could be the neighbourhood for you.
Want to know more about the dynamic neighbourhoods of Oakville? You can read all of our community guides right here.
Should I sell or buy first?
Now this is a question for the ages. Once again, the answer depends on a few different factors.
- Selling first is usually the safer choice unless it is a very busy market. It allows you to know exactly how much you can spend on your new home. Plus, you won’t have to worry about your house not selling after you’ve placed an offer on a new property.
- On the other hand, buying first can have some advantages. If prices are rising quickly, you can secure your new home before they get out of control. This option also allows you to search at your leisure with no looming date when you have to move out of your existing home. There is always the slight risk that you won’t be able to sell before the closing date on your new home. In that case, you may want to get pre-qualified for financing to be sure you proceed with the purchase.
Buying first or selling first can be a complex decision. It is always best to work with an experienced real estate agent who can advise you on your options.
Maximizing the sale of your existing home makes every step of the downsizing process easier. Here are some ideas to help:
- What to Expect When Selling a House in Today’s Market
- How to Choose a Real Estate Agent to Help Sell Your Home
How much is my house worth?
Real estate values work similarly to other commodities in that they are primarily driven by supply and demand. For the last several years, there have been far more buyers searching for properties than there are listings. With so much demand and very little supply, housing prices have risen substantially over the last decade.
However, there are other factors that can affect the value of your house, including its condition, square footage, and location. Setting an accurate listing price is essential, especially if other homes are selling in your area.
How do you know where to start? Many real estate agents offer a complimentary home evaluation to let you know how your home measures up compared to others in your neighbourhood.
Do you want a clear picture of what your house is worth right now? Schedule your free home evaluation right here.
What upgrades should I make before selling?
Once you have an idea of how much your home is worth, it’s time to find ways to increase its perceived value. Keep in mind that maximizing your sale leaves you with more money in your bank account, which opens up more options for your future. Depending on how much equity you have, you might even be able to buy your new house outright. With so much at stake, making a few minor upgrades that increase your home’s value is well worth it. Here are some ideas to start with:
- Get out your cleaning supplies and scrub your house until it shines. A deep clean of your floors, windows, sinks, and counters will help make your home appear brand new.
- Consider a new coat of paint. Painting is simple and inexpensive, yet is one of the best ways to add perceived value to your home. Light or neutral colours add a modern flair, and can even make the rooms feel bigger.
- Replace old light fixtures. New chandeliers and lamps add a touch of brightness and style to your home.
- Touch up the kitchen and bathrooms. These two rooms are high-priority for many potential buyers. You likely don’t need a total overhaul. Some attractive new backsplash and new silicone could be all it takes.
- Add some smart technology. A smart doorbell and thermostat can make your home more appealing to younger, environmentally-conscious buyers.
Is there anyone who can help me with all of this?
The best part of downsizing is not having to do it alone. Recruiting close friends and family members won’t just take much of the stress and hard work off your shoulders, but can make the process a lot more fun! You might have to throw a pizza party into the deal, but sorting through your belongings and touching up your house will become a much more enjoyable experience.
For more complex jobs, it is always advisable to bring in experienced professionals. If you feel like your contact list is lacking, there is no need to worry. A local real estate agent can put you in touch with every expert you need to ensure a smooth transition to your new life in Oakville.
Are you thinking about buying or selling and are curious about what it’s like in the current market? I am happy to provide you with the latest stats and accurate information you need to make an informed choice. Email me today or call 416.884.7925 with any questions you may have.

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