Toronto house dropped its asking price by more than $3 million

It's no secret Toronto house prices have been dropping like they're hot for a while now.

And this sprawling Rosedale estate is no exception.

We first wrote about 27 South Dr. back in 2024 when it hit the market with an eye-watering $20,800,000 price tag.

The foyer. 

After sitting for 184 days without finding a buyer, the listing was pulled. Now, nearly two years later, it's back on the market for $17,490,000.

The primary ensuite. 

For those of us who can't do math in our heads, that's a substantial $3.31 million haircut.

A guest bedroom. 

Although when you really think about it, that's only about 15 per cent off — basically the luxury real estate equivalent of a store offering to cover the tax.

The butler's pantry. 

Still, unlike many of Toronto's ultra-pricey mansions that lean hard into flashy, oversized, and vaguely casino-adjacent design choices, 27 South Dr. has always been one of the rare trophy homes with actual taste.

An aerial shot of the property. 

Originally built in 1902, the Edwardian home sits on a massive 50-by-296-foot lot in Rosedale backing onto a private ravine.

The family room. 

The home underwent an extensive restoration, renovation, and expansion under architect Ray Murakami, with interiors by Ann Johnston and landscape design by Mark Hartley, and was even featured in OBJEKT Design Magazine.

The recreation room. 

And as far as anyone can tell, not much has changed since its 2024 listing.

The front of the house. 

From the street, the home still has all the restrained elegance you'd expect from a historic Rosedale property, but inside it remains a masterclass in contemporary luxury.

The sauna. 

The four-level home, complete with an elevator, blends Edwardian architecture with sleek modern interiors and enough wellness amenities to make most luxury spas feel under-equipped.

The family room and kitchen. 

The main floor centres around a stunning open-concept kitchen and family room complete with a custom butler's pantry and coffee station.

The dining room. 

There's also a formal study with a fireplace, custom pocket doors, and a wet bar that opens into the dining room, which features a climate-controlled glass wine cellar capable of storing 370 bottles.

The gym. 

The home still offers five bedrooms and nine bathrooms, along with a home theatre, gym, massage room, infrared and rock sauna-steam combo, and a cold plunge bath for anyone fully committed to biohacking their way to immortality.

The backyard. 

Outside, things somehow get even more luxurious.

A view of the ravine. 

The ravine-side backyard has been transformed into a full-blown resort setup with a pool, heated stone terraces, and an all-seasons cabana complete with a bar and louvre pergola system.

The study. 

One curious detail remains: there's still no garage.

The primary bedroom. 

For a home at this price point, that's always felt like a bit of an eyebrow-raiser.

The family room and kitchen. 

This time around, though, the listing notes that drawings are available for a future two-car garage if the next owner feels their luxury car collection deserves better than open-air driveway parking.

The backyard and the back of the house. 

So... progress?