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Listings 4 years ago

A Rosedale Heritage Home Rich in History

All it takes is a wander through Rosedale to know you have arrived in a very special neighbourhood. This coveted community is steeped in history and tradition from the architecture of the homes, to the homeowners themselves. As you explore the area you will find impressive century-old structures, sylvan parks, the Rosedale ravine, and an abundance of warm and welcoming neighbours.

Rosedale was built primarily between 1900 and the early 1930’s, inspired by Frederick Law Olmstead’s Garden Suburb street pattern. The desire for a Canadian influence in art and architecture was strongly felt during this post-war period, translating into houses with epic grandeur and unique features. 


Map of North Rosedale in 1923, Goad’s Atlas. Government House was the official residence of the Lieutenant Governor of Upper Canada and Ontario, and was located in what is now known as Chorley Park, located just a few doors away.

This affluent neighbourhood was once the estate of William Botsford Jarvis, a member of the Family Compact, a group of men who had most of the political and economic power in Upper Canada. His wife named the area “Rosedale” after the wild roses that grew plentifully in the area. In 1864 the Jarvis family sold the estate, allowing for residential development to begin soon after. Below are some images sourced from the Toronto Archives that depict Rosedale in the early days. 

A Rosedale Heritage Home Rich in History




Within this neighbourhood, there are a few houses that stand out as landmark residences. Perfectly perched above the Evergreen Brickworks and the Don River, 208 Roxborough Drive is one of them. 


The exterior of 208 Roxborough Drive at dusk.



One of our favourite perspectives of 208 Roxborough Drive: the large open foyer with views through to the dining room and family room.

Over the course of its 86 year history, this prestigious address was the backdrop of hundreds of neighbourhood soirées, where the city’s most interesting residents would gather and be hosted in the tradition of the day.  Many Rosedale residents will say that the early December party at 208 Roxborough Drive was the highlight of, and proper kick-off to the festive season each year.

One can picture arriving in formal attire to the home, glittering in holiday finery, traveling up the stone walkway and entering into the grand open foyer with its long views to the oversized living room, dining room, library and family room. This spectacular home afforded an idyllic environment for spectacular and memorable parties. 

After cocktails, guests would select from an expansive array of gourmet delights and then cosy up to the sofa or chair of their choice throughout the main floor. Only the grand staircase was reserved for the four adult children to perch with their partners, to casually dine and savour the party below.


The grand staircase leading to the upper floor is one of a kind with hand-crafted detail.

Another highly cherished memory for the family was the annual Christmas Eve ball hockey tournament that took place in front of their home and attracted neighbours of all ages and skill levels. One family would contribute the hot chocolate, another the treats, while someone else would bring the nets – a neighbourhood tradition that provided memories for a lifetime. There was also the traditions of the “moveable feast,” where neighbours travelled to each other’s homes to enjoy a seven-course dinner and the spectacular catered Christmas coffee party, where it seemed as though every single neighbour in Rosedale was on the guest list. These traditions continue in new and modern ways, bringing together this wonderful neighbourhood. 

The icing on the cake for the owners of 208 Roxborough, was its location on a quiet street. The owners’ children could play outside for hours and seldom see a car go by. To this day, this quiet cul-de-sac remains one of the safest places for kids to play basketball and ball hockey in Toronto. It’s also one of the city’s secret neighbourhoods where you can see kids walking to and from school.


An aerial view of the cul-de-sac in which 208 Roxborough is situated on.

Living in the same home for over sixty years is almost unheard of in this day and age, but for the owners, they couldn’t imagine anything else. The size and sophistication of this home allowed for the children to have ample spaces to sneak away with a “dorm” style bedroom and a large playroom in the basement. When the current owners first saw 208 Roxborough Drive, the number one thing that appealed to the family was its magnificence.  While a superb place for wonderfully large parties, the home also has so many quiet, intimate spaces that make it homey for those times when only two people are in residence. 


The elegant yet inviting seating area that looks out onto the backyard.

Having spacious rooms on two floors also had strong appeal. It’s a rare gem in an area populated with three-storey homes. The prevalent charm and elegance provides the perfect environment for grand parties and social events. It truly is the perfect family home in all respects. 208 Roxborough Drive offers an unmatched opportunity for a new family to now own one of the city’s most impressive heritage homes full of outstanding period details and beautifully appointed rooms. This landmark ravine estate is more than just architecturally impressive, it’s a warm and welcoming home, ready for making new memories. 

With an enticing sense of arrival through the manicured front garden, this house draws everyone in with its magnificent bay window and stone-clad façade. The grandeur of the foyer with stunning ceiling detail leads to generously proportioned principal rooms, perfect for entertaining. The main floor showcases an elegant living room with picturesque windows overlooking the charming landscaped garden. 


208 Roxborough’s oversized living room, adorned with beautiful bay windows.

Climb the beautifully hand-crafted staircase to five large bedrooms including an enviable master retreat with office and ensuite. The private backyard offers a gardener’s oasis with layers of lush green surrounds and ravine views. Lovingly-maintained for decades, this home offers the ultimate mix of elegance, refinement, character and untold opportunities.


Rosedale backyard oasis with ravine views.

For more information regarding 208 Roxborough Drive, please contact Cailey at 416.424.4910.