A $12M Toronto mansion comes with stained glass window portrait of original owner

Toronto real estate is full of character homes, but few can say they come with a built-in portrait of the woman who once lived there.

At 114 Glen Rd., in the heart of Rosedale, a stained glass likeness of Mrs. Applegate gazes down from the staircase landing — a self-portrait that's been watching over the house since it was built around 1910.

"This house has so much history," says realtor Donna Thompson.

The stained glass window of Mrs. Applegate. 

"The original owners, the Applegate family, actually built two homes in Rosedale. There's even a stained glass window of Mrs. Applegate herself — it's such a rare and charming detail."

The formal dining room. 

But it's definitely not the only charming detail of this historic home. 

The family room with coffered ceilings and oak wainscotting. 

Designed by architects Simpson and Young and inspired by Italian Renaissance master Andrea Palladio's Villa Rotunda, the home looks like something straight out of a European estate tour.

The central hall. 

The stately octagonal central hall is framed by twelve Ionic columns, and the craftsmanship throughout is jaw-dropping.

The living room with a mosaic fireplace. 

There's hand-carved oak wainscoting, intricate plaster ceilings, and fireplaces that look like they belong in a museum.

A marble bathroom. 

The current owner, an architect who has lived here for 25 years, has taken great care to preserve the home's historical integrity while updating it for modern living.

The primary bedroom with an original fireplace. 

The result is a stunning mix of grandeur and comfort across more than 7,500 square feet of living space.

The living room in the loft. 

There are seven bedrooms and eight bathrooms, including a dreamy third-floor loft that feels like a secret retreat among the treetops.

Bow windows in the family room. 

Massive bow windows flood the rooms with natural light, and the ten-foot ceilings make everything feel even more expansive.

The downstairs recreation room and kitchen. 

Downstairs, you'll find a recreation room with its own fireplace, an exercise room and the laundry room.

The main floor kitchen. 

The home also boasts not one, not two, but three kitchens — which, in recent years, has allowed the property to function as a triplex.

A bedroom. 

Since around 2011, the second and third floors have been rented out as fully furnished apartments.

The third-floor kitchen. 

The third-floor loft, a three-bedroom, two-bath unit, was last leased for just under $4,000 a month, while the second-floor one-bedroom went for $2,500.

Another bedroom. 

While the property is now being sold as a single-family home, a little potential rental income certainly doesn't hurt.

The backyard. 

Outside, the property has lots of potential.

Various sitting areas outside. 

The 100-by-122-foot lot is surrounded by mature trees and gardens, and there are apparently saline pools and an infinity hot tub tucked away in a corner of the yard somewhere, too.  

One of three bedrooms on the third floor. 

The detached two-car garage and extra driveway parking are practical perks, but let's be honest, it's the history and architecture that steal the show here.

A bathroom. 

As Thompson puts it, "It's truly a once-in-a-generation home. You just don't see this kind of craftsmanship or connection to Toronto's past anymore."

The back of the house. 

The asking price for 114 Glen Rd. is $11,788,000 — but for the chance to own a piece of Rosedale's history, some might call that priceless.