Welcome back to Pick Five!

This week, we’re not touring dream homes or hidden gems. We’re pulling back the curtain on something far more telling: Toronto listings that prove just how out of touch some pricing strategies have become in 2025.

If you’ve been browsing condos lately, you’ve probably noticed a familiar pattern:
A unit gets listed high. It doesn’t sell. Then it gets re-listed lower… with an offer date.
Sound familiar? That’s because this tactic—once a hallmark of a red-hot market—is still being used by agents who haven’t updated their playbook since 2021.

But here’s the reality: buyers in 2025 are savvier, slower to jump, and less willing to play pricing games. This week’s Pick Five highlights listings that reek of strategy without substance—homes that were mispriced from the start and are now floundering in plain sight.

Why This Pricing Model No Longer Works

• The market has normalized. We’re not in a frenzy anymore. Buyers can compare listings, wait things out, and spot desperation a mile away.
• Holding back offers doesn’t signal strength—just confusion. Especially when paired with a recent price cut or relist.
• Re-listing low doesn’t reset memory. The listing history is public, and buyers remember what you were asking last month.
• Pricing psychology matters. If the numbers don’t make sense, the story doesn’t either—and buyers check out.

Let’s take a look at five Toronto condos that showcase exactly what’s going wrong.

Five Condos That Got the Strategy Wrong

• 375 King St W #2502 – $699,000 | The Too-Late Discount: Originally listed at $799K, this one came back down to earth with a $100K price drop—then asked for offers. The result? Crickets. The market smelled the misfire.
• 36 Lisgar St #1411 – $499,000 | The Mixed-Messaging Special: Listed with no offer date, then switched to a holdback… all while lingering. Buyers aren’t confused—they’re just done.
• 120 Parliament St #2203 – $649,000 | The Bait and Switch: From $739K down to $649K with a fresh offer night attached. It’s still active, still unsold, and still trying to revive expired hype.
• 19 Grand Trunk Cres #1511 – $799,000 | The Relist Loop: Listed, pulled, re-listed, pulled again. Two different strategies, same result: zero urgency, zero offers.
• 88 Scott St #2006 – $719,000 | The Disappearing Act: Quiet holdback, little marketing, no traction. A textbook case of a listing that needed a strategy, not just a price.

The Verdict: Time to Let Go of 2021

What we’re seeing in this week’s Pick Five is a failure to adapt. These aren’t bad condos. In fact, most are well-located, well-laid out, and priced within reason now. The problem is how they got here—and what that says to buyers.

Here’s what today’s sellers (and agents) need to accept:

• The market doesn’t respond to manipulation. It responds to clarity.
• Buyers don’t chase properties anymore. They analyze them.
• “Repriced with offer night” isn’t a strategy. It’s a contradiction.

What Should Replace the Old Model?

• Transparent pricing from Day One.
• Targeted marketing that respects the listing history.
• Clear timelines, not theatrical ones.
• A focus on value, not vibes.

Which Listing Left You Shaking Your Head?

Was it the third relist on Grand Trunk? The $100K haircut on King? Drop your thoughts in the comments—especially if you’re a buyer who’s been watching these play out in real time.

And if your agent is still pushing a 2021 pricing playbook, maybe it’s time for a conversation.

Want more sharp, honest breakdowns of Toronto’s real estate market?
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