🏠Should You Sell First or Buy First in

Hillcrest Village, Pleasant View, Don Valley Village, or Bayview Woods–Steeles?

This is one of the most common questions I hear from homeowners in North York.
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If you’ve lived in your freehold home for many years, the decision can feel stressful. Toronto timelines and prices make this choice more complicated than it used to be.

There is no one right answer — both options carry risks.

Selling First

Selling first gives you clarity. You know exactly how much your home sold for and how much you have to work with.
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The risk is timing.
In Toronto, freehold closings often take 60 to 90 days. That means once your home sells, you may need to find your next place within a set timeframe. If the right home isn’t available, you may feel rushed.

Another concern is temporary housing. Some homeowners worry about needing short-term arrangements if buying takes longer than expected.
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Buying First

Buying first can feel more comfortable. You take your time choosing your next home and avoid the pressure of moving twice.

The risk here is financial.
If your current home takes longer to sell — or sells for less than expected — carrying two properties at once can become stressful. Bridge financing may be required, and that cost adds up.

In neighbourhoods like Hillcrest Village, Pleasant View, Don Valley Village, and Bayview Woods–Steeles, freehold homes do not all sell at the same speed. Layout, condition, and pricing play a big role.

What Makes This Decision Harder Today
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Toronto’s market is less predictable.
Some homes sell quickly. Others take time. Online headlines don’t reflect individual properties very well.

That’s why many homeowners take a careful, step-by-step approach — reviewing timelines, finances, and personal comfort before deciding.

This isn’t a decision to rush.
Understanding both sides helps homeowners move forward with confidence, whatever they choose.