July 2, 2022 | Good to Know

Downtown Toronto Skyline

The most expensive Toronto neighbourhoods have long been on this famous list. These wealthy neighbourhoods have been in the top rankings for the better part of 100 years. Rosedale, for instance, goes as far back as being one of the most affluent neighbourhoods before the 1900s (only Parkdale, yes, you read that correctly, was wealthier before the 1900s.) Many of these neighbourhoods are what dreams are made of for Torontonians. Large lots, beautifully large homes, leafy streets, the list of amenities is longer than we could write about.  Let’s dive into the most expensive Toronto neighbourhoods.

Bridle Path

The largest properties are found in the Bridle Path. Gated properties and ultra-luxury homes are the minimum entry point here. You may have found yourself driving along Lawrence Avenue West and discovered that a permanent detour takes you through the heart of the Bridle Path. If you know Drake, then you have likely seen what he built in the Bridle Path. A hometown boy who made it big in the music industry. Look at what makes it a luxury funhouse – or maybe an opulent and overly extravagant funhouse?  It’s not uncommon for some Raptors to pop by and shoot hoops on his indoor basketball court.

York Mills

York Mill neighbourhood combines several neighbourhoods into one; Hoggs Hallow (the rarely driven hamlet-like area at the base of York Mills and Yonge Street, abutting Rosedale Golf Club), St. Andrews-Windfield and lastly, Banbury. These are some of the most sought-after real estate in Toronto. Because these are some of the early “suburban” developments in Toronto nearly 100 years ago, many large lots and newly constructed houses exist. There is an excellent mix of greeny and architecture in these neighbourhoods. It’s also home to the International whos who of business.

Lawrence Park & Lytton Park

Lawrence Park and Lytton Park are two neighbourhoods that boundary one another. People who are unfamiliar with Lawrence Park can get a little confused about the boundaries; we wrote about that here. Lawrence and Lytton Park have fantastic homes, excellent schools (one of us is an LPCI grad), and a great park system that runs down to the water.

Lawrence Park & Lytton Park Homes For Sale

Toronto park near Lawrence Avenue

Forrest Hill

Forrest Hill was long held as the home of Ted Rogers (founder of Rogers Communications) – interestingly enough, he grew up in Rosedale (which is on our list.) It was also the temporary home of Drake (mentioned above.) Forrest Hill is a quiet stretch west of Upper Canada College, with Bishop Strachan School nestled in the middle of the neighbourhood.


Rosedale is one of the fabled downtown neighbourhoods. If you are looking for turn-of-the-century architecture, incredible lots, deep Toronto history and old money, Rosedale is the place to be. The streets are great; the homes are what dreams are made of. It’s also a wonderful spot if you want to be near downtown but also feels removed. There are two easy ways out of town to escape to the farmhouse or cottage (Bayview Extention and the DVP are right there.)

Rosedale Homes For Sale

Moore Park

Moore Park is found on the north end of Rosedale. Undoubtedly, the expansion of Toronto’s elite one hundred years ago saw an opportunity to create Rosedale-like lots with newer homes. Moore Park is one of the favourites in Toronto; no one drives through the area accidentally; it’s all locals as it is often overlooked because only a few roads give people access to the neighbourhood.


The wealthiest condo owners are drawn to Toronto’s luxury condo market, which is Yorkville. It’s not uncommon to see Yorkville condos sell for more than $3500 a square foot.  Walk down any of these streets, and you will see one supercar after another. This is where the International elite likes to spend their days. Great restaurants and cafes are found throughout Yorkville.

Yorkville Homes & Condos For Sale

Toronto continues to evolve into one of the most expensive cities in the world. It’s no wonder there is so much to do in the city. Also, major corporations have their offices downtown. Many elite business owners and families have their homes thought this list of Toronto’s wealthiest neighbourhoods. By no means is this list exhaustive, but these are the rock-solid investment neighbourhoods in Toronto – no matter what phase the real estate market is in.

Not all Toronto neighbourhoods are created equal. We pride ourselves on guiding our clients to the right purchase. Contact us today – we can chat about the best neighbourhood investment for you!

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