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.
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.