10 of Ontario’s Most Expensive Homes

By Josh Sherman | 7 minute read

Pictured above, a home on a secluded, resort-like private island is one of the 10 most expensive properties available on the Ontario housing market this August.

There’s at least one thing Toronto’s luxury homebuyers and your average house hunter have in common: low housing supply has been impacting both this year, albeit at very different price points.

In March, new listings hit a 20-year low in Canada, as Toronto saw a 44.3% decline. The luxury segment wasn’t immune, Sotheby’s Top-Tier Real Estate: 2023 Mid-Year State of Luxury report suggests. “Despite a delayed start to the spring market, Canada’s largest luxury real estate market gained steady traction through the first half of 2023 as the City of Toronto continued to attract buyers and investors from its position as the epicentre of the nation’s economy and as the primary hub for immigration into Canada,” according to the report, which defines luxury homes as those priced north of $4 million. “However, pervasive housing supply challenges continued to preclude potential sales and to frustrate the needs of prospective homebuyers,” the report continues.

While luxury listings have trended lower this year, there are still many jaw-dropping upscale properties on the market, and, if a recent rebound in overall listings is any indication, there may soon be even more. We’ve scanned the Wahi listings to showcase 10 of the most expensive homes on the market in Ontario right now. Note we haven’t included private sales or investment opportunities such as vacant land (like this listing). Continue scrolling to see the province’s priciest listings.

1. 1775 Ridge Rd, Oro-Medonte  

The price: $37,000,000
The property: The rural township of Oro-Medonte is located on the northwestern edge of Lake Simcoe and known as a desirable recreational destination for southern Ontarians. It’s also where you’ll find the most expensive house in the province.

That waterfront home, set back on the shores of Kempenfelt Bay, east of Barrie, has a host of amenities that seem to embrace Oro-Medonte’s vacation vibes. There’s an outdoor and indoor pool and spa, expansive terrace, tennis court, boathouse, and guesthouse. 

In the main residence, you’ll also find a butler’s kitchen and pantry, nine bedrooms, 15 bathrooms, a wood-panelled library, elevator, home theatre, wine cellar, games room — need we say more?  

2. 1 Bloor St. W., unit 8000, Toronto  

The price: $34,981,778
The property: Paying $35 million for a lower penthouse suite in a yet-to-be-completed Toronto condo building may seem outrageous — and we’re not saying it’s not — but there is some logic behind the heady pricing.

This penthouse is located in The One condo development, which is currently under construction at the southwest corner of Yonge and Bloor and poised to become Canada’s first supertall (more than 300 metres tall) tower. Although it looks like another skyscraper will steal the crown of tallest residential building in Canada from The One, if you want a fancy condo in a supertall tower in Canada right now, no other options exist. And that, it appears, is where the law of supply and demand comes into play with the sky-high pricing.

It’s impossible to know exactly what the units will look like upon delivery, but slick renderings give an idea, going so far as to depict a walk-in closet full of designer shoes and handbags — probably not off the mark for the type of buyer the unit will attract.

3. 2275 Doulton Dr., Mississauga  

The price: $29,900,000

The property: This house has some clout. Featured in the Amazon Prime superhero series “The Boys,” the French chateau-inspired estate, known as the Saint George Mansion, is garnering a bit of a following on Instagram — which isn’t something that can be said for most houses. 

In an interview with the Star last year, the listing agents pointed out a number of standout features. These include a grand foyer with 40-foot ceilings, a home theatre finished with custom seating by Italian automaker Lamborghini (in bright red, of course!), and a private nightclub. 

“It’s for people who want to entertain. That would be for somebody like a very, very high-end athlete who would buy that house to entertain,” Robert Bourelle, one of the agents representing the listing at the time of the Star interview, told the newspaper.

4. 1-J24 Fawn (& Birch Islet) Island, Muskoka Lakes  

The price: $29,500,000
The property: This listing, previously featured by Wahi as one of the five Ontario cottages you’ll want to live in full-time, encompasses an entire 2.5-acre private island. The island, known as Fawn Island, is on star-studded Lake Joseph, a major hot spot for celebrities looking for a slice of cottage life.

Fawn Island is a veritable village on the water. It comes with five separate structures: the main lodge, an east and west boathouse, a canoe house, and a glass house. The main lodge screams classic Muskoka, with vaulted ceilings, hard-wood everything, and rustic stone accents.

5. 1272 Fiddlers Green Rd., Ancaster  

The price: $29,000,000
The property: OK, so normally in a listing roundup, you’d see outside and inside the homes. Apparently, that isn’t possible here — not unless you’re willing to sign a non-disclosure agreement, the Hamilton Spectator reports. What we can see without entering a binding agreement is still pretty impressive. Take the pool, which earlier this summer earned this home a spot in a previous Wahi roundup, “Make a Splash: 8 Ontario Homes With Amazing Pools.”

Of course, the listing also provides some insight into what you can expect from the interior: 26,000 square feet of living space, including a 24-seat home theatre with 254-inch screen, as well as a gourmet kitchen and lofted nanny’s quarters. 

6. 103 Old Colony Rd., Toronto  

The price: $28,800,000

The property: As much as possible, this picture-perfect 21,000-square-foot house was designed to exist in harmony with its natural settings. It’s the result of a years-long collaboration between architectural power couple Michael and Lisa McCann. Their artistic vision is depicted in a series of paintings quite unlike the usual listing photos used to promote most properties.

It took more than 100 tradespeople to make the couple’s vision a reality, Lisa said in a recent interview with Toronto Life. “I didn’t want this to be a subdivision on steroids,” she told the magazine. “I wanted to bring as much functionality as possible so that residents would never want to leave.”

To that end, the home’s got its own cellular antenna and a dedicated underground filtration system and a bevy of stay-at-home amenities, such as a home theatre equipped with karaoke, teleconferencing, and virtual reality capabilities. 

7. 30 High Point Rd., Toronto  

The price: $28,000,000
The property: Originally listed nearly a year ago, this ‘70s modernist mansion was designed by noted architect John C. Parkin. Haven’t heard of him? Maybe you’re familiar with some of the design projects he was involved with: Toronto City Hall, Yorkdale Shopping Centre, and the National Gallery of Canada.

There’s no shortage of space here. The eight-bedroom home’s 1,700-square-foot recreation room is bigger than the median-sized Ontario house, and a central solarium space spans four storeys and is capped with giant skylights.
 

8. 1250 Waldmere Rd., Bracebridge  

The price: $25,000,000
The property: For a few million less than a private Ontario island, you can buy an entire peninsula in Bracebridge, roughly three hours north of Toronto. 

This 1.5-acre finger of land in Muskoka is surrounded by water on three sides, meaning nature is your only neighbour here. Whoever buys the 11,500-square-foot recreational home will get nearly 700 feet of unobstructed lakefront access and 270-degree views of the water.  The interior is adorned with warm, vintage finishes rather than the cool, sleek stylings of many other luxe listings.

9. 1343 Blythe Rd., Mississauga  

The price: $24,500,000
The property: Described as a French-influenced manor home, this opulent seven-bedroom dwelling sits on 10 verdant acres of land backing onto the Mississaugua Golf and Country Club and overlooking the winding Credit River.  

Stone walls and wrought-iron gates shield this secluded-yet-centrally located property from prying eyes, although you don’t require an NDA to take a peek inside.

Finished living space totals nearly 20,000 square feet and includes six gas fireplaces, a billiards room, wine cellar, and hardwood floors throughout. 

10. 11 High Point Rd., Toronto

The price: $23,900,000

The property: Just up the road from the seventh most expensive home for sale in Ontario, 11 High Point Rd. represents the second listing entry on the list within Toronto’s most exclusive neighbourhood, the Bridle Path. The châteauesque estate has some distinct features.

For example, there’s a so-called Scarlett O’Hara staircase. (For those who don’t know, that’s a staircase with two separate entry points — think the Titanic staircase.)

The backyard is a shaded oasis. It’s a perfect spot to kick back and contemplate how not that long ago, in 2015, this home was listed for $12,800,000, which is 60.5% cheaper than today.