From a carriage house to a Canadian music legend's home base to a cozy retreat, 1194 Stirling Drive in Oakville has really seen and done it all. 

The four-bedroom, four-bathroom home used to be the carriage house of the Stirling Estate and apple orchard, which included the 1879 lakestone and stucco house at 114 Wolfdale Ave. and a barn. 

But sometime in the 19th century, 1194 Stirling Dr. became its own address when the land was split up. 

The garden is filled with perennials. 

Now, the carriage house has been transformed into a stunning residence. 

The kitchen looking into the rest of the house. 

Much of the transformation took place when Canadian music legend Tom Cochrane, the guy who sings the 1991 chart-topper "Life is a Highway", owned it back in the early 2000s. 

One of the bedrooms. 

According to the current owner, he took the old post-and-beam house and added a third storey and two soundproof studios at the side of the house, where he used to record his music. 

A bathroom. 

The house then passed through two more owners before being bought back in 2012 by the current owner.

A large deck perfect for enjoying the summer. 

She told blogTO that her and her late husband were out for a drive and happened upon the open house for 1194 Stirling Dr. For her late husband it was love at first sight. 

Another view of the garden. 

"I did not love it," she told blogTO, laughing. But after her late husband promised she could renovate it to her liking, she changed her tune.

A bedroom with wood beams. 

Now, the beautiful home offers an impressive 4,294 square feet of living space with four bedrooms and three and a half bathrooms. 

The primary bedroom. 

"It’s a great home," says the owner. "Very homey. Very earthy. There are tons of earthy tones. It's not a sterile environment. You have to be close to nature to love it."

The primary ensuite bathroom. 

Not only are you surrounded by trees and have views of the lake, but the home itself is filled with natural materials. 

The dining room. 

From the exposed pine beams to the abundance of stones in the bathroom, kitchen and adorning the gas fireplaces, you really experience that seamless indoor-outdoor living.

The pool. 

Not to mention, there are six doors that lead to the large backyard deck that's surrounded by the garden, and the piece-de-la-resistance is a new custom Gib-San Gunite pool, which was installed in 2022.

The large yard. 

But the owner's favourite part of the house is how great it is for entertaining. 

Old beams add warmth and character to the house. 

"I can entertain inside or out," the owner told blogTO, explaining how she designed the kitchen to have everything she'd need for hosting big parties. 

The kitchen leads out to a sunroom. 

It features top-tier Miele appliances, a warming drawer, heated countertops, two copper sinks, and a copper pot filler—all complemented by heated tile floors throughout.

The living room with skylights. 

And while much has changed since Cochrane owned the house, there are still some signs of the rock and roll star throughout the home. 

The former studio turned family room. 

For example, the two soundproofed studios are still there but now they're a guest bedroom and a family room. 

The other studio turned guest bedroom. 

"Soundproof rooms are great for the children," the owner mentioned.  

The back of the house. 

Another favourite aspect of the house according to owner is the location. 1194 Stirling Dr. is located right between downtown Oakville and Bronte. 

A sitting room. 

"I can walk everywhere," she said.

The sunroom. 

1194 Stirling Dr. is currently listed for $3,999,990, which is down from it's earlier listing price of $4,350,000.

The front of the house. 

The owner explained that they reduced the price as she's very motivated to sell so she can move closer to her family.