The History of Rosedale

Before its carefully charted development as a high-end suburb in the latter half of the 1800s, Rosedale was the site of a vast private homestead which, as legend suggests, was abundant with wild roses.

The vast Rosedale estate was eventually divided up for formal residential development, attracting affluent buyers to the area. In the early 1900s, Rosedale played an important role in the political landscape of the city and province as it was home to Ontario’s fourth Government House, known as Chorley Park.

Living in Rosedale

Often considered one of Toronto’s top luxury enclaves, Rosedale offers a refined, high-end quality of life. Residents (many of whom rank among the city’s most notable) are drawn to the neighbourhood’s charming tree-lined streets and decadent suburban ambiance. The area’s proximity to top-ranked public and private schools also makes Rosedale especially attractive for upper-class families.

Rosedale also sees comparatively limited turnover among residents, with most homeowners choosing to live in the area for several decades. This trend lends to the neighbourhood’s close-knit atmosphere and reputation for exclusivity.

Housing Stock in Rosedale

Rosedale is home to an abundance of gorgeous historic homes, many of which sit on generously sized lots. Larger Edwardian, Georgian, and Tudor properties are most prominent – many of which hold designation under North and South Rosedale’s Heritage Conservation District (HCD). This ensures that many homes have some measure of protection against demolition or uncharacteristic alteration.

Given Rosedale’s upscale heritage, compact housing options are limited in the neighbourhood centre. However, a modest selection of modern condos has emerged along Yonge Street in recent years.

Our Rosedale Favourites

• Don Valley Brick Works Park: A historic industrial site turned green space and cultural hub, Don Valley Brick Works Park is a unique oasis unlike anywhere else in the city. At the centre of the park is Evergreen Brick Works. Once a busy factory throughout the nineteenth and twentieth centuries, the historic 16-building campus has been thoughtfully restored and modernized, today hosting educational programs, farmers’ markets, art installations, community events, and more.
• Toronto Lawn Tennis Club: A popular spot for private leisure and socialization, the historic Toronto Lawn Tennis Club is the oldest active lawn tennis club in the world. Considered a world-class facility, legends of the sport such as Björn Borg, Martina Navratilova, and Chris Evert have all trained here.
• Craigleigh Gardens: Nestled in the heart of the neighbourhood, Craigleigh Gardens is a charming and scenic green space complete with rustic walking trails and an off-leash dog park. The park is also a gateway to the lush and vast ravine system – a popular area for walking, running, cycling, and more.
• Quanto Basta Restaurant: One of Toronto’s best Italian restaurants, Quanto Basta serves a delicious range of staple dishes and authentic delicacies using high-quality ingredients.

What Stands Out in Rosedale?

One of Rosedale’s most essential charms is its serenity. Despite being located just beyond the cusp of downtown Toronto, the neighbourhood’s quiet streets feel well-removed from urbanity, with a quaint private ambience. As a neighbourhood that’s remained resistant to high-density development, this one-of-a-kind atmosphere will almost certainly remain preserved for future generations.