$12 M house with glass-ceiling wine cellar one of Toronto’s most expensive homes to sell last month
Published November 7, 2025 at 4:21 pm
While the average price of a home in Toronto is down month over month to just over $1 million, some properties in the city are still selling for eye-watering sums.
Last month, the city saw a few luxurious properties in Rosedale and Yorkville–two of the city’s swankier neighbourhoods–sell for well over $5 million. Not unexpectedly, these homes offer a ton of space, a lot of style and magazine-worthy interiors.
Here’s a look at the five most expensive houses that sold in Toronto in October, courtesy of real estate website and brokerage Zoocasa:
18 Chestnut Park Rd.

Called “Architectural Digest-quality” in the listing, this six-bedroom, seven-bathroom house in Rosedale just sold for $12,200,000 after being listed for $13,995,000.

The home, which also boasts a two-storey coach house with a double-car garage, features a circular drive and exterior surface heating. Inside, the house offers a large foyer, a gourmet kitchen, a mudroom, a state-of-the-art master bedroom with his-and-hers walk-in closets, and a finished basement with a movie theatre/custom golf simulator and gym.


135 Crescent Rd

Another Rosedale property, this seven-bedroom, six-bathroom home, sold for $9,622,500 after being listed for $9,995,000.

Known as “Horsman Hall,” the rare listing sits on a semi-private road and features herringbone-patterned European white oak hardwood flooring, an open-concept living and dining area with a wine bar and wine fridge, a private library and a chef’s kitchen with a floating eat-in counter. The home also offers original leaded glass, a rec room with a wet bar and a home gym and more.

112 Hazelton Ave

This luxurious and sophisticated Yorkville home, located on Hazelton Ave., sold for $8,000,000 after being listed for $8,998,000. The house, which the listing says evokes images of “a classic London home in Knightsbridge,” offers four bedrooms, five bathrooms, and over 4,400 square feet spread across four storeys. The home also boasts Juliette balconies, ensuite bathrooms attached to every bedroom, an elegant chef’s kitchen, a two-car garage with a coach house, a glassed-in wine cellar and more.


74 Chestnut Park Road

This house, which sold for $7,100,000 after being listed at $7,250,000, looks and feels historic, boasting many early 20th-century touches.

The seven-bedroom, five-bathroom Rosedale home was built in 1903 by Langley & Langley architects and offers spacious front and rear gardens, a large detached double garage, high ceilings, eye-catching windows, and classic craftsmanship. The home is close to Yonge Street, top schools, parks and ravines.

123 South Drive

Another Rosedale gem, this sophisticated four-bedroom, five-bathroom home sold for $6,350,000 after being listed for $6,888,000.

The house, which the listing says blends heritage and contemporary luxury, offers a gourmet kitchen with a statement island and professional-grade appliances, a home office and a spacious master bedroom with a dressing room, spa-like ensuite and a private terrace. It also offers an in-ground pool with a waterfall, a two-level backyard deck, an outdoor kitchen, an infrared sauna, a fitness studio, and more.

