Your Home Is Not Selling. Now What?

Your Home Isn’t Selling. Now What?

Here’s what nobody tells you about selling a home in this market: the number on the sign matters way less than the reason you’re moving in the first place.

I had Dana Rashard on the Supply and Demand podcast — she’s been in real estate since the 1980s and coaches agents at Richard Robbins International who do 600+ deals a year. She’s not guessing. She’s working with data from thousands of actual transactions across Canada. And the thing she kept coming back to surprised me, because it’s not about pricing strategy or market timing. It’s about why you’re selling at all.

The “why” thing sounds fluffy. It’s not.

Dana made a point that I think every seller in Toronto and York Region needs to hear right now. People don’t wake up one morning and say “hey honey, I think we made a hundred grand on our house — let’s sell.” That’s not how it works. You’re selling because you need more space. Because the kids are gone and the house is too big. Because you got transferred. Because your parents need you closer.

Those reasons don’t disappear because the market shifted.

“One thing that everyone should focus on — real estate agents, buyers and sellers — is you want to really focus on why are they moving… They don’t normally wake up and say, ‘Hey, honey, you know what, I think we made a hundred grand on our house. Let’s sell it.’ A homeowner doesn’t. They normally have a reason why they’re selling.”
— Dana Rashard, Richard Robbins International

The problem is that once the process starts, everyone defaults to price. They get anchored to what their neighbour sold for in 2022. Everything becomes about whether they’re “leaving money on the table.” And while they’re obsessing over that, the actual reason they needed to move — the growing family, the aging parents, the retirement plan — just sits there, waiting.

“What we do is we forget about that through this whole process. And when you forget about it, we default to price… You should always be revisiting the reason why you’re selling, because people are selling every day because they have a good reason why.”
— Dana Rashard

This isn’t motivational poster stuff. It’s a decision-making framework. When you stay connected to your actual reason for moving, you evaluate offers clearly instead of emotionally. You can weigh the cost of waiting against the cost of putting your life on hold. That’s a fundamentally different conversation than staring at a number on a screen and feeling sick.

So what about the “down” market?

This is the mental trap I see sellers fall into constantly. They look at peak prices from 2022 and feel like they’re losing money. And I get it — a $400,000 difference on paper is gut-wrenching. But Dana broke this down in a way that I think reframes the whole thing.

“If your house has depreciated from when you bought it, probably the whole market has too. So it’s all relative. You should always be buying and selling in the same market.”
— Dana Rashard

Here’s the math, and this is important. If the market is down 10% across the board, your $1.5 million home dropped $150,000. But the $2.5 million home you want to move into? That dropped $250,000. The gap between the two went from $1 million to $900,000. You’re actually closer to your next home than you would have been during the frenzy.

Dana calls this “the delta” — the gap between what you sell for and what you buy for. And in a softer market, that delta actually shrinks for people moving up. Which is kind of counterintuitive, right? The market feels worse, but the math is better.

“If you are in a move-up position, this is the best time ever to buy. If you are a first-time purchaser, it’s a good time to buy because interest rates are low. There’s lots of inventory to choose from.”
— Dana Rashard

And for people downsizing or retiring, the cost of waiting is a whole different conversation. Dana put it bluntly:

“If you’re close to retirement, how long can you put it on hold? When you’re 70 years old, you put something on hold for a couple of years, your life could change. Medically, it could change.”
— Dana Rashard

That’s not something people like to think about, but it’s real. The financial cost of selling lower is a number you can calculate. The cost of putting your life on hold for three years? That’s harder to quantify, and it might be a lot higher.

If your home isn’t selling, stop doing small price drops

This was one of the most useful things Dana shared, and it goes against what most agents will tell you. The old approach was to reduce by 5% every two weeks — a slow step-down that’s supposed to find the right price. Dana’s coaching data from high-volume agents across Canada says that strategy is broken.

“Rather than reduce it 5% every 15 days, if you did a 10% reduction after 25 or 30 days, people think that is a better deal. And we’ve seen people create more activity, more action, and they sell quicker.”
— Dana Rashard

Think about it from the buyer’s side. A small price drop signals desperation without creating any real urgency. You’re basically telling buyers “yeah, we know it’s overpriced, but we’re not ready to admit how much.” A meaningful reduction — one that genuinely puts you in a new price bracket — changes how buyers perceive the value entirely. They look at that gap between original and new price and think opportunity.

And here’s the other thing: consider relisting instead of just reducing. When you terminate and relist, the MLS treats it as a brand-new property. Buyer search alerts fire again. People who dismissed it the first time actually look at the photos, read the description, give it a fair shot.

“By doing a relist, they tend to go through the listing in deeper [detail]… even though it has a good price reduction, they just are, ‘Oh yeah, I didn’t like it before. It’s just cheaper now.’ And they don’t review the listing enough.”
— Dana Rashard

Death by a thousand cuts with tiny incremental drops, sitting in front of the same uninterested buyers for months — that’s not a pricing strategy. That’s just slow bleeding.

The last 5% of every deal is pure emotion

This is something I think about constantly, especially as someone who uses AI and data tools every day. Technology can get you close. It can put you in the right price range, surface the right comps, automate the marketing. But it can’t close a deal.

“Doing real estate is a very emotional action and activity. And so you really need to be there to help guide a client through the process. Because when you have two parties that are highly emotional, you need a lot of human skills to sort of smooth things over to create a win.”
— Dana Rashard

Dana put a number on it that stuck with me:

“The last 5% of the deal — pure emotion. And it’s up to the agents to know their party so that they can decide, is this something that is right for my client?”
— Dana Rashard

The data might say a home is worth between $1.45 and $1.55 million. Nobody’s getting ripped off anywhere in that range. The question is whether two people making the biggest financial decision of their lives feel confident enough to actually pull the trigger. That confidence doesn’t come from a spreadsheet. It comes from trust.

And on the AI pricing thing — I asked Dana directly, because I wanted her honest take:

“I truly believe a good agent like yourself knows what we call the micro market — meaning some streets demand or command a little better price. I think AI misses that part… I’ve found working with AI, they’re close, but it’s not 100% accurate. A good agent in every aspect tends to make it sharper.”
— Dana Rashard

She’s right. AI doesn’t know that one particular court in Vaughan commands a premium over the next street over. It doesn’t know whether the renovation was done with permits. It doesn’t know the reputation of specific school catchments. The best approach — and what I do — is use data as the foundation and then layer in the local knowledge that sharpens the number.

Trust without expertise is hope. Expertise without trust doesn’t close.

Dana made a distinction that I think every seller needs to hear:

“A consumer chooses to work with somebody — they’re looking at, do you know what you’re talking about? Are you a professional? Are you an expert? And do I trust you?… People won’t move forward if they don’t trust you. You might have all the right words… but in real estate, because it’s such an expensive purchase, you have to be knowledgeable, but equally important — they have to trust you.”
— Dana Rashard

Her coaching data backs this up: agents who went fully digital and stripped out the human element actually saw their businesses decline. When they brought the personal touch back — while keeping the tools and data — results improved. That tracks with what I see every day. You can have the sharpest CMA in the world, but if the person across the table doesn’t trust your judgment when things get stressful, all those numbers are just noise.

The takeaway

If you’re thinking about selling in this market, the advice from 40 years of data and thousands of transactions boils down to this: remember why you’re moving, because that reason hasn’t changed. Stop comparing to peak prices — you’re buying and selling in the same market, and the delta might actually favour you. If a price adjustment is needed, make it meaningful and consider a relist. And choose your agent based on whether you trust their judgment under pressure, not just their marketing package.

The market is what it is. Your life doesn’t have to wait for it.

Frequently Asked Questions

Is now a good time to sell a house in Toronto?

Yes — depending on your situation. If you’re moving up to a larger home, the price gap between your current property and your next one has likely narrowed, meaning you come out further ahead despite lower headline prices. If you’re downsizing for retirement, the cost of waiting can be significant — both financially and personally. As Dana Rashard puts it: “In every perspective, in my mind, it’s a great time to buy and sell real estate. This is a great market because you can get on with your life and still make it work.” The key is buying and selling in the same market so the relative math works in your favour.

How much should I reduce my asking price if my home isn’t selling?

Based on coaching data from agents doing high volume across Canada, a 10% reduction after 25 to 30 days generates significantly more buyer activity than incremental 5% drops every two weeks. Small reductions keep you in front of the same buyers who already passed. A meaningful reduction repositions your home in a new price bracket and changes buyer perception. Pairing the reduction with a relist — so the property appears as a new listing — further increases engagement.

Should I wait for the market to recover before selling?

That depends on why you’re selling. If your reason for moving is life-driven — more space, downsizing, relocation, family needs — then waiting means putting your life plans on hold for an uncertain timeline. Remember that the home you’re buying has also come down in value, so the net financial impact of selling in a softer market is often much smaller than sellers expect. If you’re purely an investor with no urgency, waiting is an option — but even then, carrying costs and opportunity costs are real.

Can AI accurately price my home?

AI valuations are a useful starting point but not a final answer. They process large datasets effectively and can get you into the right general range. However, they miss micro-market factors — specific streets that command premiums, renovation quality, school catchment nuances, and local buyer preferences. The most accurate pricing combines algorithmic analysis with an experienced local agent’s knowledge. As Dana Rashard notes: “AI is close, but a good agent tends to make it sharper.”

Why does trust matter so much when choosing a real estate agent?

Because the last 5% of every real estate transaction is pure emotion. The data can tell you a home is priced fairly. But when both buyer and seller are stressed, second-guessing, and dealing with the largest financial decision of their lives, trust is what gets the deal across the finish line. Dana’s coaching data shows that agents who removed the human element and went fully digital actually saw their business decline — their clients wouldn’t move forward on decisions because the trust wasn’t there. Expertise tells you your agent knows the market. Trust tells you they’re acting in your best interest.

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