You Call This A Real Estate “Listing Strategy?”

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7 minute read

October 12, 2026

If your 6-year-old child looked up at you and asked, “What is a strategy?” what would you tell them?

Before looking at any online definitions, I might offer, “A strategy is a well-thought-out plan of action that is enacted to provide an intended result.”

Now, let me look online…

Google A.I. says:

A strategy is a careful, long-term plan or method designed to achieve a specific goal or competitive advantage when resources are limited.

I don’t want to disagree with the almighty Skynet, but the line about “limited resources” doesn’t need to be part of the definition.

How about this one from Merriam-Webster:

A careful plan or method for achieving a particular goal usually over a long period of time.

I think that’s probably more in line with my bias toward defining the word.

Let’s look at what Wikipedia says:

Strategy is a general plan to achieve one or more long-term or overall goals under conditions of uncertainty.

Bueno.

So let’s say this: a strategy includes a “plan” of one kind or another, and that plan is utilized to achieve or produce a desired end result.

If you were a listing agent for a Toronto house or condo right now, what strategy would you implement?

The answer is “it depends.”

It depends on the size, style, and condition of the property, the location, the property type (especially house versus condo), and the price point.

But two other factors play a major role in a listing strategy, or the lack thereof (which I should call a “strategy” in quotations), and they are:

1) Agent experience, knowledge, and ability to not only assess market conditions, but also share the true market conditions with the seller.
2) Seller expectations and knowledge of market conditions.

We’ve talked about this a lot on the Toronto Realty Blog over the last few years, especially as properties have become harder to sell.

Last week, I wrote about all of the “Re-Listing” activity happening in Toronto, specifically for properties that fail to sell on the offer night, which are then re-listed at a higher price.

October 5th, 2026: “Does Re-Listing At A Higher Price Actually Work?”

Today, I want to talk about some rather “interesting” listing strategies, and I chose to put the word interesting in quotes instead of strategy, just to get us started.  As we roll through these, I think you’ll begin to question the strategy part of the equation, and eventually come to the same conclusion that I have.

I think I’ll give these names today.  And while I’m add it, I’ll add a hint of cynicism…

–

Listing Strategy #1: “Making An Impossible Task Even More Impossible”

It was between that, or “Shooting Yourself In The Other Foot,” as you’ll see shortly.

For those of you who aren’t paying close attention to the luxury housing market, I’ll say this: it’s fickle.

It’s unpredictable and it’s uncanny.

Some houses sell quickly while others don’t sell at all.

Of course, seller expecations and market value play a huge role, and there are a lot of builders listing for 20% above fair market value and those houses simply have no chance of selling.

In the $4,000,000+ price range, I would say that it’s primarily a buyer’s market.  There are areas where inventory is limited and/or in demand, and earlier this year, I wrote blogs about how there aren’t enough $3.6M – $4.2M quality homes in Leaside to satisfy demand.

But on the whole, it is not a seller’s market above $4M.

One of the strangest listings I’ve see in the fall is this one:

This house was listed for $4,795,000, and while I don’t know what this is worth, I can tell you what it’s not worth: $4,795,000.

There is not a lot of demand for this product, or this product in this area.

Suffice it to say, it’s a buyer’s market for a house like this.

That’s why it was so odd to see the seller terminate the listing after only seven days and completely switch strategies.

Er, I mean, “strategies,” since the following makes zero sense:

Wait, what?

Did they just drop the price by $800,000?

No, of course not.

Instead, their new “strategy” is to reduce the price (after only 7 days on the market…) and hold an offer date.

Check this out:

Here’s what’s always bothered me about the concpet of listing low with an offer date after listing higher…

In a red-hot seller’s market, you can take a $1,200,000 house, list it for $899,900 with an offer date, and produce 14 offers that would drive the price beyond the $1,200,000 “value” for the home, and perhaps fetch $1,250,000.

But in a buyer’s market, to take a $4,795,000 listing, re-list at $3,995,000 with an offer date, and expect anybody to “bid” on this house is perhaps the dumbest thing I’ve seen in a long time.

Oh, wait, that’s not true.

Because doing this is one thing, but doing this over the Thanksgiving long weekend is a whole other level of stupidity.

–

Listing Strategy #2: “Zig When Everybody Else Zags”

We’re in a declining condo market.

We’ve been in a declining condo market for quite some time.

A while ago, a client of mine emailed me a listing in a downtown Toronto condo and said, “This is over-priced, but if it sat for a while, and they’d take dramatically less, I’d be into it.”

Here’s the listing:

This property sat on the market at $699,999 for 47 days, as you can see above.

They re-listed for $689,900 a short while later:

The listing sat on the market again, this time for 31 days.

As the listing continued to sit, my client and I both waited to see if they would eventually terminate and re-list even lower.

Maybe $679,900 next time?  It should probably be $649,900 if they’re serious about selling.

The property was re-listed thereafter.

However, the price wasn’t really in a range of what I would say makes it “likely” to sell:

That’s madness.

Out of curiosity, I contacted the agent.  He never answered his phone, despite four attempts.

Eventually, he texted me, and I asked if this was a typo.

He said that they had done a bank appraisal for the condo and that it was “worth” $800,000.

Fascinating!

Nobody wanted to buy it when it was at $699,900 or $689,900, so the bank stepped in and decided it was “worth” $800,000.

The agent told me, “Make an offer or stop wasting my time.”

I looked him up.  He’s done one sale in the last 12 months.  So eat it…

–

Listing Strategy #3: “Fool Me Once, That Should Be Enough”

This one is exciting!

I saw a unit for sale in a building where I own an investment condo, and I was immediately intrigued:

At $489,000, this seemed a bit high to me.

I own the same floor plan, and unlike many investors, I’m honest with myself.  I would love for this to be worth $489,000, but it’s not even close.

Just shy of three weeks into the listing, the price was slashed dramatically.

A “normal” price change from $489,000 might be down to $469,000, but certainly not this:

I showed it to somebody on my team, and he said, “Maybe they really want to sell.”

But my spidey-sense was tingling.

I didn’t trust this listing.  I didn’t trust this price.  And I certainly didn’t trust the listing agent.

So I called him!

Here’s the conversation, which I found fascinating for many reasons:

Listing Agent: “Hello?”

David: “Hi, is this Jimmy Agent?”

Listing Agent: “Yes.”

David: “This is David Fleming from Bosley Real Estate.”

Listing Agent: “Okay.”

Not off to a great start, right?  I’m always fascinated by real estate agents that lack basic social decorum, let alone the ability to converse in a business that is all about relationships.

David: “I noticed you had 123 Fake Street, #321 up for $489,000 and now it’s at $429,000.”

Listing Agent: “Yes.”

David: “So are they going to consider $429,000?”

Listing Agent: “What?”

David: “Well, there’s a lot of nonsense out there in the market, so before I show this condo, which is at $429,000, on the market 20 days, and no offer date, I wanted to make sure you’re not in the ‘nonsense camp’ with all the other agents.”

Listing Agent: “Huh?”

David: “Would your client accept an offer of $429,000.”

Listing Agent: “No.”

David: “So why are you priced at $429,000?”

Listing Agent: “Because we want people to come see it.”

David: “Then what?”

Listing Agent: “Huh?”

David: “When they come see it, and they like it, and they undoubtedly offer $400,000 or $415,000, then what?”

Listing Agent: “Then the seller would probably sign back at the previous list price.”

I love working in real estate.  I really do.

But I’m embarrassed to be associated with this human.

–

Listing Strategy #4: “Pretend It’s February Of 2022”

This makes absolutely no sense to me.

Recall in Listing Strategy #1, I noted that taking a listing and dropping the price while setting an “offer date” doesn’t usually bear fruit.

But what about slashing the price?

This condo was listed at $999,000 and on the market for 79 days:

Actually, it was listed for $1,050,000 first, then the price was reduced to $999,000.

But all told, it was up for 79 days in that first listing.

Then came the second listing:

This didn’t work, as the property sat for 18 days.

So what’s the next logical step?

Probably $899,000, and I would imagine that would bring people through the door.

But what about getting crazy and listing for $799,000 with an offer date?  You know how I feel about that, right?

Well, these folks didn’t take that angle.

Nope.  Their strategy was different.

This is a new one…

That’s wild!

Credit to the listing agent for the “strategy,” I suppose.

They’ll certainly get people through the door, and they might even see offers, but what will those offers look like?

The problem is: if this strategy doesn’t work, then the seller has to re-list for $899,000, and the listing history will just drive buyers away…

–

Listing Strategy #5: “Apples To Apples, Except One Apple Is Better Than The Other Apple”

Did I tell you that my mom is into crafting?

Under current Canadian law, all women must take up knitting as a hobby once they turn seventy, and my mother is a law-abiding citizen!

She got so into knitting, in fact, that she started setting up tables at church fairs and small markets to sell her knitted wares.

It’s a hobby, and nothing more.  But she’s really, really into it!

Every so often, however, she sets up a table only to find that the table right next to her is another happy senior who wants to sell knitted hats for ten dollars.

Dang.

Imagine if that happened in real estate?

Couldn’t happen, right?

And worse than two houses being listed for sale, side-by-side, would be if those houses also happened to be attached.

Like these, for example:

These houses are identical.

There might be different fruit in the bowls in the kitchen, but they’re the same build.

Now, let’s say that you’re the seller of the house on the left and you list it for sale at $2,188,000.

Kind of like this:

Gorgeous house!

Wonderful location!

Excellent neighbours!

That’s all well and good, but let’s say that you own the house on the right, and you want to sell too!

You wouldn’t go to market at the same time, right?  That would only strengthen the position of any buyer interested in one of the two houses!

Alright, but let’s throw in another curveball.

Let’s say that you own the house on the right, and you want to sell too, but “you” are the Bank of Nova Scotia!

That’s right.  You’re the bank; you’ve foreclosed on the house, and now you’re selling it on the open market.

But your neighbour is selling the identical house.

So what’s your strategy?

This:

No catch here, folks.

There’s no offer date.  There’s no bait-and-switch.  No smoke and mirrors here.

This is merely a situation where a house is up for sale for $1,725,000 while the identical house next door is offered for $2,188,000.

Apples to apples.

Just like I said…

–

Folks, I know that many of you actively track the market, so if you’re monitoring any bizarre listings out there right now, please feel free to email them to me.

The idea for this blog post was given to me by my very own team member, Lindsay Milnes, who said, “Dave, you have to write about these two houses listed for sale, side-by-side, it’s crazy!”

Thanks, Linds!

Happy Thanksgiving, everybody!

Written By David Fleming

David Fleming is the author of Toronto Realty Blog, founded in 2007. He combined his passion for writing and real estate to create a space for honest information and two-way communication in a complex and dynamic market. David is a licensed Broker and the Broker of Record for Bosley – Toronto Realty Group

Find Out More About David Read More Posts

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