Buy First or Sell First? Two Toronto Case Studies That Show Why Strategy Matters

Part 2 in a 5-part series

Theory is helpful — but real-world examples tell the story best. Here are two Toronto clients facing the same decision, who landed on very different strategies.

Case Study #1: Buying First Made Sense

Here’s how this played out in the real Toronto market.

These clients were searching for a rare, unicorn home type — only a handful sell each year. Waiting until after selling could mean years in limbo or renting indefinitely.

Their current home? A starter property in a desirable neighbourhood that sells quickly, even in a slower market.

Strategy: Buy first.
They’re patient, prepared, and confident their sale will move smoothly when the time comes.

Case Study #2: Selling First Was the Safer Play

Here’s how this played out in the real Toronto market.

This client’s desired home type appears regularly — several options each month. But their current home is in a slower-selling area, with longer days on market and uncertain pricing.

Strategy: Sell first.
Selling was the harder piece — so they tackled that first, knowing buying would be easier once the sale was complete.

The Takeaway

Both strategies were “right” — for different people, different homes, and different neighbourhoods. This is exactly why blanket advice doesn’t work in real estate.

Thinking about buying or selling real estate?