5 Thornwood Rd., Toronto, Ont.
Asking Price: $18.5-million
Taxes: $41,346.59 (2025)
Lot Size: 63 by 248 feet (irregular)
Agent: Gillian Oxley, Royal LePage Real Estate Services Oxley Real Estate
The backstory
More than 20 years ago, Gillian and Steven Sylvester stood next to a grand house perched on the edge of a ravine in Toronto’s exclusive Rosedale enclave and envisioned a home for their family of five.
There was one major challenge to overcome: The house, designed by Eden Smith & Sons in 1908, had been split vertically in the 1960s. Each half belonged to a different owner, and only the rear portion was listed for sale.
“We bought the back half on the condition of getting the front half,” says Ms. Sylvester.
Negotiating a deal with the second homeowner took about six months.
“She knew that we wanted the whole thing, so it was tough,” she recalls.
The home’s dining room, which can accommodate 18 people.Birdhouse Media
Ms. Sylvester was familiar with the work of Mr. Smith, who was a renowned architect in the burgeoning city of the early 1900s. His commissions included churches, library branches, and public buildings. Many of the houses he designed still stand in neighbourhoods such as Rosedale, Forest Hill, Wychwood Park, High Park and the Annex.
The house at 5 Thornwood Rd. has several characteristics of the Arts & Crafts style Mr. Smith was known for, including a steeply pitched roof, a tall chimney and leaded windows with small panes of glass.
Ms. Sylvester admired the elevations, the proportions and the architect’s practice of placing the entrance along the side of the building, away from the street.
Once they had secured the property, the couple and their three young children moved into the back portion while the front was undergoing renovations.
The main and second levels feature an oak floor laid in a herringbone pattern.Birdhouse Media
The house today
“The first reno was to put the house back together,” says Ms. Sylvester, who trained as an architect and worked mainly on commercial buildings. “I certainly love a project and a challenge.”
Today, the house has six bedrooms, five bathrooms and a powder room in 8,917 square feet of living space.
To start, Ms. Sylvester refurbished the wide original staircase and lifted the ceiling height in the foyer.
There’s a formal living room with leaded glass windows and a dining room that can accommodate 18 for dinner.
When the time came to work on the back half, Ms. Sylvester had a mud room and the former servants’ staircase removed in order to make more space for a new kitchen.
The original front door was moved to a rear entrance and positioned so that a family crest carved into the heavy oak now faces the interior.
Some rooms were quite austere, she recalls, because one part of the house had been a rental property for a time. She restored details and had the leaded windows renewed.
Next to the kitchen, she created a comfortable family room with a gas fireplace, walls panelled in imported wood and French doors opening to a patio.
“It’s the place people want to be,” says Ms. Sylvester.
Upstairs, the home has a large primary suite with a sleeping area, a home office and an ensuite bathroom with an oval stand-alone tub and a walk-in shower.
There’s a second bedroom and a den on that floor. The third floor has four additional bedrooms and two bathrooms.
The family excavated the basement to create higher ceilings. Today, there’s a recreation room, kitchen, gym and climate-controlled wine room.
An elevator connects all levels.
The family room has a gas fireplace and wood-panelled walls.Birdhouse Media
Throughout the main and second levels, worn floors were replaced with oak laid in a herringbone pattern.
“I don’t think there ever was a time when there wasn’t a renovation,” she says.
Outside, the Sylvesters oversaw tree planting and extensive work on the ravine in order to prevent erosion.
Today the children are grown. Mr. Sylvester passed away a few years ago, and Ms. Sylvester would like to see new stewards take over the large heritage-designated home.
“All our kids have great memories there,” she says. “It needs to be filled with a family.”
The best feature
About eight years ago, Ms. Sylvester undertook another extensive renovation. The kitchen was updated with new cabinets, two islands and built-in appliances.
A breakfast area has French doors opening to the terrace overlooking the ravine.