Toronto mansion listed at over $18 million is like a fairytale castle

If you've ever wondered what it looks like when classic Toronto architecture gets the full glow-up treatment, let us introduce you to this jaw-dropping Rosedale estate.

Originally built in 1908 by famed architect Eden Smith — the guy behind some of the city's most charming Arts and Crafts homes — 5 Thornwood Rd. is one of the original Rosedale mansions.

"It's iconic," says listing agent Gillian Oxley of RLP Oxley Real Estate, noting how people always stop and take pictures at the gates with the fox statues.

The foyer. 

But this home hasn't always looked this good, at least not on the inside. According to Oxley, around the late '60s or early '70s, during the energy crisis, the house was converted into a duplex. 

The living room. 

The current owners, who have been in the house for 20 years, bought the back half of the home first, with the right of first refusal for the front. 

The dining room. 

When the opportunity came, they snapped up the other half.

The family room. 

"Once they got the whole house, they underwent a huge renovation," Oxley explains. "And over the years, they've continued to improve it."

The basement. 

In fact, as recently as 2021, they renovated the basement. 

The family room. 

Now, the result is nearly 9,000 square feet of sophisticated, modern living that still manages to keep that timeless Rosedale charm.

The primary bedroom ensuite. 

Inside, every detail has been carefully considered.

The second-floor living room. 

"[The owner is] an architect, and the attention to detail is unbelievable," says Oxley, noting features like the bronze kitchen backsplash, the custom walnut millwork, and rich wood panelling. 

The main floor with metal doors by Discreet & Discrete. 

The main floor is a series of unique but interconnected spaces, with subtle design details that tie everything together.

The primary bedroom. 

"One of the things I love about the house is that there are several different themes," says Oxley. "It's almost like being in a story. Every room has a different feel — it makes a magical experience."

The kitchen wit heated floors and built-in appliances. 

And the kitchen? It's a showstopper.

Svend Nielsen designed the kitchen. 

Two massive islands, dual ovens (one steam), heated floors, and two dishwashers mean you could host Thanksgiving for the entire neighbourhood without breaking a sweat.

A bedroom with an original fireplace.

On the second and third floors, you'll find the bedrooms. 

One of six bedrooms. 

5 Thornwood Rd. features six bedrooms and six bathrooms in total. 

The home office. 

There's also a second-floor family room and a private office, making it perfect for both entertaining and working from home.

The wine cellar. 

Downstairs, the finished lower level boasts nine-foot ceilings, radiant-heated floors, a full gym, naturally climate-controlled wine storage, cedar closets, and even a second kitchen.

The coach house. 

But as stunning as the interiors are, the backyard might just steal the show.

The backyard patio. 

The deep ravine lot comes with private stone stairs that lead directly into Toronto's trail system — a rare and serene escape right in the heart of the city.

The view up to the house from the ravine. 

5 Thornwood Rd. is listed for $18,500,000.