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Toronto's best residential streets

King of Kensington

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Oct 5, 2007
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Use any criteria you like - prestige, streets you think are underrated, whatever. What are our best streets, blocks and micro-neighborhoods?
Chestnut Park. Its public realm is exquisite--a narrow roadway flanked by a public boulevard of broad lawns, lush mature trees, red-brick sidewalks, ornate street lights and buried electrical wires. The houses themselves are restored old mansions with lush gardens.

For a more middle class downtown street--Palmerston with its ornate gates and original antique street lights.
Palmerston was the first street to come to mind - always elegant and its generous dimensions summon up a regal sense of history. Ravina Crescent, in The Pocket, is lovely too - charming curves and plenty of trees. Chaplin Crescent - a great alternate way to cut a diagonal across the north end of the city and take in some very fine homes. I'm sure there are many, many more.
Wow, where to start? A few of my favorates that quickly come to mind, mostly in the old city - Danforth between Broadview & Logan, Kensington Market, Queen West between Bathurst & Gladstone, Markham Street between Bloor & Lennox, the Distillery District, almost anywhere on the U of T campus - most notably (probably my favorate) Philosopher's Walk, Parliament Street between Wellesley & Gerrard, Queen East between about Coxwell & Neville Park, Evergreen Brickworks/cycling along the Don River, Gerrard between about Greenwood & Coxwell, Queen's Quay between Yonge & Bathurst, College St. between about Bathurst & Grace, Spadina between Bloor and pretty much the lake, Dundas between University & Kensington, Church St. between Charles & Carlton, King West between Yonge & Spadina, Front St. between Church & Sherbourne.... where to stop?! We live in such a great city.
While it isn't my all time favourite, and may not even be on my top 5, MacPherson Avenue between Yonge and Avenue Road is just beautiful.
To add to that, it would be a crime for me not to mention Chestnut Park a block to the southeast. Red brick sidewalks, old fashioned lighting, amazing houses... the works really.
Agree with the multiple expressions of Chestnut Park and Palmerston Blvd.

Chestnut Park is a bit of a reluctant one, since I wouldn't want to live in Rosedale even if I had the money to buy there (I prefer an area with more of a mix of people), but Chestnut Park stands out as a classic grand street.

Palmerston Blvd. too. I'd love to live there. In general, I'm a huge fan of the area realtors are calling the South Annex. Markham between Harbord and College is very nice as well. In Harbord Village, the lower block of Brunswick has a bit of an elegant feel, but I think Robert is my favorite HV street.
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Yeah Rosedale & Moore Park is probably the most beautiful residential area in Toronto. The houses, street, trees and surrounding ravines & trails all contribute to it.

The others that come to mind are the Beach/Beaches and the Ward's Island.
Bay st between Dundas and Bloor.
Queen's Quay between Yonge and Spadina.
Sherbourne st between Queen and Carlton.