$20M Toronto Bridle Path home hasn’t sold in 15 years, why?

#GTAHomeHunt is a weekly series from the Star that gets into the details of real estate listings in Toronto and the Greater Toronto Area. Have a tip? Email us at [email protected]

It’s no secret that the magnificent homes in Toronto’s Bridle Path are accessible to only a few. They carry price tags in the millions of dollars and often sit on the market sometime before they’re sold.

But one home in the exclusive area where Drake resides, is currently listed for $20 million and has been on and off the market for 15 years, jumping nearly $1 million in price per year from its 2007 sale price of $5,750,000, according to House Sigma.

Sounds like a long time to find a buyer?

Ongoing GTA Home Hunt real estate expert Othneil Litchmore weighs in on the seller’s possible motivations, what the market is like in the area and how long others have been waiting to sell their mansions.

Prices: $20,000,000

Neighborhoods: Bridle Path-Sunnybrook-York Mills

The property has been on the market for a year and was also listed every two years from 2008 to 2016, as well as in 2017, 2019 and 2021.

What makes 20 High Point Rd. unique?

Sitting on a 2.16-acre lot, the more than 5,000-square-foot home at 20 High Point Rd. is equipped with five-plus-one bedrooms, 10 bathrooms and a six-car garage.

According to House Sigma, the property also features a walkout basement, a dance floor, bar, sauna, exercise, party and games room, a tennis court, a “gardener’s apartment with a separate entrance,” and elevator access to all three levels of the home — not to mention a water fountain on the driveway.

“It’s (a property) for people who do a lot of entertaining — a record executive, or a socialite,” Litchmore said.

Despite the bells and whistles, however, it has most recently been on the market for nearly a year, and was also listed every two years from 2008 to 2016, as well as in 2017, 2019 and 2021.

Between those listings, it also appears to have been leased out, costing $53,000 per month each time — a hefty price tag for an average person, but a deal for someone looking to live lavishly without committing to owning a home of this size, Litchmore said .

Between those listings, it also appears to have been leased out, costing ,000 per month each time.

Why has it been listed on and off for the past 15 years?

Compared to neighboring properties, the home does appear to be a little outdated, Litchmore said, which may be a factor into why it hasn’t sold recently.

Its neighbour, 11 High Point Rd. — a property made famous by the 2004 movie “Mean Girls” — is listed for $23,800,000, and has been on the market since February. That property features a more modern appearance, fresher landscaping and more bedrooms and bathrooms.

Other, relatively cheap properties (around the $9 million mark) have sold in mere weeks, while others have sat on the market for months before being snatched up, Litchmore said. Still, they’ve sold.

But renovations needed and cheaper properties nearby might not be entirely the reason 20 High Point Rd. hasn’t sold in 15 years, especially as both foreign and domestic buyers looking for expensive and status-driven new digs may view the Bridle Path as the place to be.

“Something tells me the seller isn’t very motivated to sell,” said Litchmore. “The fact it’s on the market for as long as it is, it’s more of a reflection of the seller’s motivation than it is of any market conditions.”

Or, Litchmore said, it could be a situation similar to Michael Jordan’s, who has been trying to sell his Chicago mansion for the past 10 years, for which he pays more than $100,000 in annual property taxes, according to Business Insider.

That 56,000-square-foot property on seven acres of land was originally listed for $29,000,000, but is now going for $14,900,000.

“They’re white elephants,” said Litchmore, referring to these megahomes. “The things are so unique that they just can’t be sold.”

"They're white elephants," said realtor Othneil Litchmore, referring to these megahomes. "The things are so unique that they just can't be sold."

Tips for finding a place like this?

The Bridle Path, famously one of Toronto’s most exclusive neighborhoods, is one of the only places in the city to find properties like this.

That is, if you can swing the multimillion-dollar price tag that comes along with it and the risk of sitting on the property for a while when you decide you’re ready to leave.

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