How to Find a Real Deal in Toronto Real Estate

The buyers who walk away with the price everyone talks about aren't the luckiest. They're the ones looking in the right corners of the market — and ignoring the noise everyone else is chasing.

Every few weeks I get a version of the same message: someone saw a sale price on a house — in Leaside, in Davisville Village, in Moore Park — and couldn't believe it. "How did they get that?" The honest answer is almost never luck. It's almost always process. Here's the process.

Stay Flexible Within Your Neighbourhood and Home Type

You can absolutely find a deal in Rosedale, or in a detached home specifically — you just have to widen how you define "the right one" inside that box. Buyers who insist on one exact street, one exact layout, or one exact lot size are competing against everyone else chasing that same narrow target. Buyers who stay open within the neighbourhood or the home type they actually want see more of the market, and more of the market means more chances to find the listing that's been overlooked. A Davisville Village side street instead of the main strip. A Leaside triplex instead of a detached. A Lawrence Park property just outside the boundary that still gets the school catchment.

To be clear, how tightly you define your criteria doesn't determine how much room you have to negotiate — that comes down to the seller's situation, not yours. What flexibility does is put more listings on your radar, including the ones where that room to negotiate already exists.

Ignore Days on Market

Most buyers read days on market backwards. The assumption is that a listing sitting for a month means a desperate seller ready to take anything. Often it's the exact opposite. A property that's been sitting for a while may well have already had offers — and the seller said no to all of them because they're anchored to a number the market simply isn't paying. That's not desperation. That's the hardest kind of seller to move, and days on market alone won't tell you which one you're dealing with.

Follow the Price Reductions

A price cut is one of the only pieces of information in this business that a seller cannot spin. It's a direct admission: our expectations were too high, and we know it. That's not a red flag — it's an opening. A seller who has already reduced once is a seller who has already done the hard psychological work of adjusting to reality. They are far more receptive to an offer under asking than a seller who just listed last week and still believes in the number on the sign.

Skip Power of Sale, Look at Estate Sales

Power of sale properties draw a crowd precisely because everyone assumes they're the easy discount. They're not — the lender is legally required to obtain the best price reasonably available, so the negotiating room is often smaller than buyers expect. Estate sales are a different story. The executors are typically under no obligation to hit market value; their priority is usually settling the estate efficiently, not maximizing every last dollar. That mandate — speed over ceiling price — is what creates genuine room to negotiate.

Executors are frequently out-of-town family members, or multiple beneficiaries who just want the process finished. A clean, fair, no-conditions offer can be more appealing to them than chasing the last five thousand dollars.

The best deal in Toronto isn't found. It's built — patiently, and in the pockets everyone else skips past.