Midtown Toronto

The symbol of Toronto’s elegant past and exhilarating future.

The story of living in Midtown Toronto is one of families. The beauty of Midtown Toronto real estate is found in its architecturally-significant homes, its peaceful streets, and its well-maintained and manicured parks and gardens.

Take A Step Back

The year is 1824, and Sheriff William Botsford Jarvis has purchased a 110-acre estate in the heart of what we will come to know as Rosedale. His wife, Mary Jarvis, will spend days riding her horse throughout the area – serving as the very foundation of Midtown Toronto’s unique charm: the beautiful, winding streets.

Fast forward to 1973, and the bustling heart of Midtown (Yonge and Bloor) is atwitter with growth. Skyscrapers are rising, almost like magic, from the ground – casting their gaze over Bloor Street – while the mature trees continue to make this one of the greenest areas of the city. The growth is palpable, and only a small sign of what’s to come…


Midtown Toronto real estate features a handful of neighbourhoods that we think you deserve to know about. Here are the ones you should see…

Forest Hill

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.

Chaplin Estates

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!


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.

South Hill

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.

South Annex

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.

Casa Loma

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.


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.


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.


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.

Moore Park

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.

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".

Check out Forest Hill!

Download our checklist here for everything you can find in the area.

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”).

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).

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!

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.

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.

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.

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.

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.

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).

Get A Step Ahead

I’d love to take the time to chat with you about Midtown Toronto real estate. If you’re interested in this area of town, or any of the specific neighbourhoods, please send me a message and we can get started right away.

Reach out today for more information.
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