Click below for more about the different neighbourhoods in this area, and some local history, as well…
Forest Hill real estate is known for having some of the best homes (often in Georgian and Tudor style – often designed by known architect Eden Smith), along with the best schools (like Upper Canada College and Bishop Strachan School). Spend more time in this area, and you’ll quickly regard Forest Hill Village as the area’s definitively charming cluster of shops and restaurants.
Forest Hill used to go by a different name – all the way up until 1967, Forest Hill was actually known as “Spadina Heights.” The new name, "Forest Hill", was the name of a summer residence of one of the earlier settlers. The name, unintentionally, is a callback to a now defunct bylaw from the 1930s, which stated that a house could not occupy more than 35% of the lot - leading to the remaining area being heavily landscaped and treed, the forest in "Forest Hill".
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Chaplin Estates retains a lot of the small-town charm of Forest Hill real estate, within proximity to Yonge Street for shopping and commuter-friendly transit options. It also includes the historic Beltline Trail, where people can run, walk, and even cross-country ski in the winter!
The history of Chaplin Estates can be traced back to the Chaplin family, who marketed this area as an upscale residential enclave back in 1913 (when the area was referred to as “Eglinton”).
Allenby is where you’re more likely to find smaller versions of Tudor-style homes, with pretty gardens in an area named after the local school. Allenby Public School is highly regarded across Toronto, specifically for their French immersion program. Keep your eyes peeled on this area, as the new light-rail transit (LRT) will tremendously benefit and change this area for the better.
The Allenby area was originally settled in the 15th century, due to it being positioned around a spring. The name itself, though, came from the area’s prestigious school (named after British soldier Lord Edmund Allenby).
Akin to Forest Hill architecture, South Hill has large properties featuring winding streets across the Beltline Trail and the ravine system. In plenty of cases, homes in South Hill offer beautiful views of the city. You’re also close to Dupont Street, which is fast becoming a hip stretch of the city home to shops, restaurants, specialty food shops, and bakeries galore.
Have you ever heard of the Republic of Rathnelly? In 1967, What began as a protest of the Spadina Expressway turned into one of Toronto’s most unique neighbourhoods. A “mock secession” led to the formation of what we now know as the Republic of Rathnelly. This South Hill enclave still holds a yearly summertime celebration to mark their independence!
The South Annex encapsulates more of that downtown energy than anywhere else in Midtown Toronto. The homes are older, generally pre- and post-turn of the century, with Victorian and Edwardian stylings. This is a great spot for younger families, with mature streets, and lots of neighbourhood parks (and dog parks, too!) Conveniently located to College and Bloor Streets, the South Annex is vibrant and has a little something for everyone.
Starting as a subdivision in the early 1850s, the neighbourhood of the South Annex has been home to some of Toronto’s most prominent and important families.
One of the best parts of living in Casa Loma is the proximity to Wychwood Barns. This former-streetcar-warehouse-turned-artistic-hub has a farmer’s market every weekend, and an ice rink in the winter (which makes for a great meeting spot). Beautiful grand homes, bending and twisting streets, and big, beautiful mature trees. Most of the homes here are Tudor in style and dot this quiet neighbourhood with a subdued kind of elegance.
Everybody knows the history of the Casa Loma mansion, but did you know what it might have potentially been after going bankrupt? There were plans to turn this historic mansion into a hotel, a school, and even a convent. Eventually, it became the tourist attraction and local landmark that we know today.
Given its proximity to Yonge and Bloor streets, Yorkville features some of the most in-demand real estate in Toronto. It helps that this neighbourhood is superbly unique, with lots of big-ticket shops, small streets (like along Hazelton, Webster, and Scollard), and lots of charm. This former bohemian haven has now become one of Toronto’s most luxurious hotspots featuring the city's most notable restaurants.
What do Neil Young, Gordon Lightfoot, and Margaret Atwood have in common? Some of Canada’s most famous and revered musical and literary figures came up in Yorkville’s hip artistic scene throughout the 1960s.
This is where you’re likely to find some of Toronto’s oldest homes. It’s easy to get lost in Rosedale with all its twisting streets, it’s easy to see why people find so much peace and quiet here. Rosedale Park is a community hub, Branksome Hall is a renowned school for girls, Mooredale Community Centre is a local highlight, and there is even easy access to the Don Valley Parkway and Downtown Toronto.
Rosedale has and has always been one of Toronto’s most desirable neighbourhoods. The lush landscape of ravines and forests is what made this Canada’s first area to have curved streets. You can find a touch of history on almost every corner, such as the gas-lit lampposts which illuminate a Toronto favourite: Chestnut Park.
There is a tremendous sense of community in Cabbagetown, alongside a strong pride of ownership. This is the height of urban living, with great shops along Parliament Street & Carlton Street. The homes might be smaller, many of them are row houses, but they have a distinct historical charm reminiscent of Toronto’s earlier days. This neighbourhood is growing all the time, so many young families have their hopes set on living in Cabbagetown.
Throughout the 1840s, Irish immigrants fled the potato famine and made the streets of Cabbagetown their home. Soon thereafter, and out of necessity, heads of cabbage sprouted from the ground throughout the neighbourhood – hence the name! Since then, Cabbagetown has changed and evolved. The Great Depression ravaged the area, while today’s residents have restored it – and all those beautiful Victorian homes – to their original grandeur.
A quiet section of Midtown Toronto real estate, bound by ravines on either side, with tree-lined streets that feature less traffic (which is perfect for children who love to get out and play Canada’s national pastime: hockey). This is the perfect place to find the right school, in a well-established neighbourhood, where playdates reign supreme.
Toronto’s first commuter rail was in existence well before the GO Train. In 1892, the Belt Line Railway was deemed to help facilitate the growth of Toronto and its surrounding suburbs. As it happens, the most notable and visually striking of these stations was located right in the heart of Moore Park. Even though the railway fell into disrepair due to the Great Depression, a well-manicured trail can be found there today – which runs 9 kilometres through many of Midtown Toronto’s neighbourhoods (Forest Hill, Chaplin Estates, South Hill, etc).
A neighbourhood centered on the popular intersection of Yonge and St Clair. It has a varied mix of semi-detached and detached homes as well as luxury condominium buildings. Many of the condo apartments have picturesque views of the city.
The area of Deer Park was referred to by the First Nations people as "Mushquoteh" which means a meadow where deer come to feed. When the Heath family purchased an area of land in Mushquoteh, they appropriately named it "Deer Park".
Summerhill is a picturesque neighbourhood full of winding streets, beautiful homes, and lovely parks, located close to Yonge and St Clair. Its appeal comes from the quiet streets that are a few minutes walk away from upscale boutiques and shops, fine restaurants and easy transportation to downtown or around the city.
Summerhill is named for Charles Thompson's two hundred acre estate, "Summer Hill" which was built where Summerhill Gardens is now. Thompson was a prosperous transportation baron who operated several cruise lines and stagecoaches.
Leaside was originally a planned community developed around the railway's maintenance yard. Many of the streets such as Hanna Road, Laird Drive, and Wicksteed Avenue, are named after railway executives. Homes are generously sized, often with a private drive. Leaside is separated into North and South divided by Eglinton Avenue. Lots of Tudor-style homes can be found here, and although there are bungalows, many of them have been replaced by bigger, custom designed homes. The future LRT will also have a stop in Leaside.
Leaside was the site of Canada's first air mail delivery on June 24, 1918, when pilot Brian Peck delivered a load of 120 letters from Montreal to Toronto. What was remarkably odd about the flight was that the plane initially had a hard time taking off, never reached an altitude of above 40 feet, and had to refuel twice. The reason for the struggling plane wasn't found out until 1954, when it was revealed that Peck had been also transporting alcohol - quite illegal during prohibition!