I am renting an apartment in the Annex for two weeks in May: partly for work, partly to visit with my son. Looking for restaurants in the Annex that a singleton would enjoy. From Vancouver, so really love good food.
Two of my favourites: Dessert Trends Bistro and Boulevard Cafe. The first is only open for lunch during the week and brunch on the weekends. The space is beautiful and on a nice day, you can sit at a two-top next to one of the open french doors. The food is wonderful -- French, with several international influences (good coffee, too) -- and the staff is sweet (and sometimes flaky). Boulevard Cafe is just down the street. Fantastic large patio, great Peruvian food. Both are on Harbord.
okay, I know that this may sound like nit-picking but technically, historically, officially and geographically, the Annex neighbourhood does not extend south of Bloor.
So you will find may fine restaurants on Harbord and they may be within walking distance but they are not in the "Annex".
Here are search results from the Ontaro places hub for restos in or near the Annex -
Personally, I like By The Way cafe and (and fine for a singleton) -
and I disliked Kilgours
By The Way
400 Bloor St W, Toronto, ON M5S1X5, CA
The Annex encompasses a large area...I like Expresso Bar at St George and Bloor..on South East corner....Miranda
While it may or (probably) may not "technically" be in the Annex, the Universal Grill is Annex-y (and a nice walk on a May evening).
I also like Bar Mercurio (again, probably out of bounds technically, but Annex-ish).
And there are lots of great picks along Harbord. Take a short walk and see what feels good to you. I find Messis very reliable. 93 Harbord is a nice Middle Eastern bistro, the Harbord Room is on my list (but I can't actually vouch).
In the Annex super-proper, I've probably been under-whelmed, but if you go further along Bloor (West), you'll hit some Korean and African as well.