Upsize in Markham: Why Today’s Market Favors Smart Moves
I’ve met many Markham homeowners this year who are rethinking their portfolios. For a lot of people, this is the moment to swap an older or underperforming property for something stronger—whether that means a better-renting unit, a newer condo, or a move from a smaller home to a bigger one. The reasoning is straightforward: many Ontario units first occupied on or after November 15, 2018 are exempt from the annual rent-increase guideline, so newer properties can support market-level rents (with proper notice and timing). If you’re stuck with a dated condo or townhouse that’s tough to rent, selling it and upgrading into a property with better rental fundamentals can be a smart pivot.
For end-users, the timing is compelling too. Upsizing has always been a natural step, and in this market larger homes have generally fallen more than smaller ones. That narrows the gap, giving move-up buyers more house for the money. While investors should be careful about buying larger, harder-to-rent homes, families who need space often find downturns are the best windows to make the change.
Negative cash flow is a bright-red flag. If you bought near the 2021–2022 peak and your property now costs thousands more per month than it brings in, it may be time to cut losses and reposition into something sustainable. The costliest mistake is clinging to a cash-draining asset while waiting for a quick rebound. Cycles take time, and waiting without a plan can put you further behind.
Most people feel safest buying when prices are rising, but the better play is often to buy while they’re falling. You won’t time the exact bottom, yet buying on the way down still captures a discount and the eventual recovery. Markham, like the broader GTA, shows signs of bottoming, but no one knows the precise turning point. What matters is setting yourself up for the long run, not chasing short-term swings. For example, I recently helped a family purchase a larger home in Cachet. We searched for nearly three months and found that well-kept, larger homes priced right were in strong demand. The final price was roughly 30%, about $1 million, below comparable sales from three years ago.
Moves aren’t one-size-fits-all. Each family should weigh whether to sell first to avoid juggling two homes, whether income is secure enough to handle a higher mortgage, and whether the target location will hold value. In Markham, school catchments, transit access, and proximity to employment hubs are key drivers of both everyday livability and long-term resale value.
For investors, stability comes first. Strong cash flow and sensible leverage are the foundations of surviving a downturn. Overextending in a choppy market can turn a long-term wealth builder into a headache. Diversify across property types and even outside real estate, one basket is rarely enough.
And don’t forget: the rental market in Markham and across the GTA remains active. Prices may wobble, but end-user demand hasn’t vanished. That’s why panic selling rarely pays. Stay calm, audit your numbers honestly, and make deliberate moves that strengthen your position instead of weakening it.
