Toronto’s most expensive home for sale this month is a six-acre Bridle Path ravine property asking $48 million, and seven of the city’s 10 priciest listings are in the Bridle Path-Sunnybrook-York Mills area. Forest Hill and Casa Loma account for the rest. One brokerage, RE/MAX Realtron Barry Cohen Homes, holds six of the 10.
These listings are arriving in a soft market: CREA reported last month that national sales had stalled for a fourth straight month, and the Bank of Canada decides on rates Oct. 28. Still, three of these homes came on the market in roughly the past three weeks. For how Toronto compares with the rest of the country, see our national list.
How we built this list: We ranked detached houses within the City of Toronto by asking price, using active listings on REW.ca checked individually on Oct. 1, 2026. Suburban municipalities such as Oakville and Mississauga are not included. None of these listings has a publicly reported celebrity owner.
A note on photos: listing photo galleries belong to the brokerages and photographers who made them, so we do not republish them. Each entry links to the full listing, where you can see the real home. Images in this story are file photos, not the listed properties.
1. Bridle Path: $48,000,000
More than six acres on a ravine come with an existing Art Deco bungalow with six bedrooms and eight bathrooms, vaulted ceilings and a marble atrium foyer. The grounds include an in-ground pool, waterfall and stone terraces. The listing markets it as a build-to-suit opportunity close to the Granite Club.
See the full listing and photo gallery: RE/MAX Realtron Barry Cohen Homes (via REW.ca)
2. Casa Loma: $34,500,000
This gated Indiana limestone estate has eight bedrooms, 11 bathrooms and more than 15,200 square feet. It has 12-foot ceilings, a private elevator, an eight-piece marble primary bath, a third-floor spa with saunas, and underground parking for 11 cars with a turntable and car wash.
See the full listing and photo gallery: RE/MAX Realtron Barry Cohen Homes (via REW.ca)
3. St. Andrew-Windfields: $30,000,000
Built by Danieli Development, this nine-bedroom, 17-bathroom house has a grand circular staircase, an elevator, an indoor basketball court, a heated pool, a home theatre and Control4 automation. The property has parking for 28.
See the full listing and photo gallery: RE/MAX Realtron Barry Cohen Homes (via REW.ca)
4. Bridle Path: $27,500,000
A French Provincial home by architect Joe Brennan, this two-acre estate has nine bedrooms, 11 bathrooms and more than 20,000 square feet. It has five fireplaces, a wood-panelled library, an in-ground pool and sports court, and a two-bedroom coach house. It was listed about two weeks ago.
See the full listing and photo gallery: RE/MAX Realtron Barry Cohen Homes (via REW.ca)
5. Bridle Path (Park Lane Circle): $22,800,000
A gated modern estate on nearly three acres with a 300-foot frontage, this home has six bedrooms, nine bathrooms and more than 14,000 square feet. It has a tennis court, pool and hot tub, glass elevators, a theatre, gym, spa and wine cellar.
See the full listing and photo gallery: RE/MAX Realtron Barry Cohen Homes (via REW.ca)
6. Bridle Path (Bayview Ridge): $22,500,000
A French-style chateau on a 3.6-acre double lot with golf course views, this six-bedroom, 10-bathroom home has indoor and outdoor pools, a tennis court, a Bordeaux-inspired wine cellar and cigar room, and seven fireplaces.
See the full listing and photo gallery: Sotheby’s International Realty Canada (via REW.ca)
7. Forest Hill South: $21,995,000
Clad in hand-selected limestone with slate and copper roofing, this seven-bedroom, nine-bathroom home has nearly 13,000 square feet on about half an acre backing onto the Beltline Trail. It has a saltwater pool, sport court, theatre, sauna and gym.
See the full listing and photo gallery: Royal LePage Real Estate Services (via REW.ca)
8. Bridle Path (High Point Road): $20,000,000
A mid-century modernist estate designed by architect John C. Parkin, this 2.12-acre property has about 26,000 square feet, eight bedrooms and 13 bathrooms. It has a four-storey solarium, a 3.5-storey atrium, indoor and outdoor pools and a Zen meditation garden.
See the full listing and photo gallery: RE/MAX Realtron Barry Cohen Homes (via REW.ca)
9. Forest Hill South: $17,995,000
Built of commercial-grade steel and concrete and extensively renovated, this six-bedroom, eight-bathroom home has 12-foot ceilings, a six-car underground garage, a home theatre, a 500-bottle wine cellar and a saltwater pool with cabana and summer kitchen.
See the full listing and photo gallery: Harvey Kalles Real Estate (via REW.ca)
10. Bridle Path (Bayview Ridge): $16,999,900
A French chateau-style stone home by architect David Wooldridge on a gated cul-de-sac, this seven-bedroom, nine-bathroom house has about 12,000 square feet on nearly an acre. It has a pool with hot tub grotto, a sports court, a putting green and a five-car garage.
See the full listing and photo gallery: Chestnut Park Real Estate (via REW.ca)
Prices are asking prices from active listings checked Oct. 1, 2026, and can change at any time.
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