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Toronto's best residential streets

I'm adding in Sorauren Ave, which provides a cool mix of restored industrial heritage, consistent residential form, park space, and some retail/commercial sprinkled in there.

There's also several other notable residential side streets east of Roncesvalles, like Fern Ave and Macdonnell Ave with quality Victorian residential housing stock.
 
I've recently checked out Alcorn Ave, which stretches from just east of Avenue Road and goes towards Yonge Street in the Summerhill Area. There's a fair amount newer built housing that are contemporary adaptations of the Victorian model, especially on the north side of the street. But there's a solid consistency in them, and lines up to quality urban residential dimensions. Reminds me of a newer version of Tranby Ave (in the Annex).

Worth a stroll:

 
Recently found this thread and wanted to add some of my favourites that haven't been mentioned being Brunswick Avenue, Beaconsfield Avenue, Silver Birch Avenue, Beaty Avenue, Ulster Street and Ridelle Avenue, each one very different from the next.
 
I live in Parkdale and I think Cowan Avenue between King Street West (to some extent Queen) and Springhurst Avenue is one of the prettiest residential streets. It’s also full of families.

View attachment 134810

I was just about to re-open this thread and mention Cowan Avenue. Biked down the street last weekend. Such a wonderful street with a great variety of heritage house styles.
 
Maybe not the best street, but certainly one with an interesting secret: Shannon St, near College and Dovercourt.

Notice anything strange in this fire insurance map from 1890?

Screenshot 2024-02-23 at 8.07.21 PM.png


Look closely at the twelve red brick houses on the south side of the street: 5, 7, and 47 to 65. They all appear to be laid out using an L-shaped plan, pretty typical of late 19th-century and early 20th-century Toronto houses. But the narrow part is facing Shannon and the wide part is facing south. That in itself is unusual, but it gets weirder.

Looking at these houses from the street, they don't read as typical Victorian bay-and-gables:
Screenshot 2024-02-23 at 8.34.18 PM.png
Screenshot 2024-02-23 at 8.31.58 PM.png


But from the back, surprise! There's the bay and gable, with lots of intricate gingerbreading visible only to residents in their backyards.

4f051_28.jpg

(via)

Sure enough, it looks like all these houses were built backwards, facing a street that never existed, with their backs to Shannon St.

Screenshot 2024-02-23 at 8.19.14 PM.png


I have no idea how this came about, but I'd love to hear some theories if anyone has any!
 
Maybe not the best street, but certainly one with an interesting secret: Shannon St, near College and Dovercourt.

Notice anything strange in this fire insurance map from 1890?

View attachment 543107

Look closely at the twelve red brick houses on the south side of the street: 5, 7, and 47 to 65. They all appear to be laid out using an L-shaped plan, pretty typical of late 19th-century and early 20th-century Toronto houses. But the narrow part is facing Shannon and the wide part is facing south. That in itself is unusual, but it gets weirder.

Looking at these houses from the street, they don't read as typical Victorian bay-and-gables:
View attachment 543127View attachment 543128

But from the back, surprise! There's the bay and gable, with lots of intricate gingerbreading visible only to residents in their backyards.

View attachment 543137
(via)

Sure enough, it looks like all these houses were built backwards, facing a street that never existed, with their backs to Shannon St.

View attachment 543138

I have no idea how this came about, but I'd love to hear some theories if anyone has any!

Hmmm, I love a challenge..........

I wonder if this has something to do with it:


It clearly appears the houses were meant to front Heydon Park Road.

Lets see whatelse we know...........

Hmmm, Ossington/Old Orchard school was founded here in 1957, it erased the homes to the south of those on Shannon. That explains the current condition in part, but not the historical one.


***

Hmmm again,

This Aerial pic from 1953 shows the area before the school was constructed:


****

Aha!

Lost Rivers does tell the story..........look here:

1708742967446.png


That green line is Garrison Creek (or a tributary)


Looks like the creek here was buried between 1890-1894
 
Nice sleuthing!
I wonder if this has something to do with it:

Heydon Villa
It clearly appears the houses were meant to front Heydon Park Road.
Weirdly, Shannon St appears to precede Heydon Park Rd. The 1884 fire insurance maps show the various Denison estates still mostly intact, with lots already subdivided on the north side of Shannon.
Screenshot 2024-02-23 at 10.27.29 PM.png


Dover Court, the original Denison estate at the top of Lake View, must have had a stream running right through the middle of it!

In the 1890 Goad's Atlas, just six years later, the houses had been built.
 

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