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Amazing photo! I'm wondering if this building with the tower is the one that still stands (with billboard now instead of tower) at the Queen-King-Roncesvalles intersection. The location seems about right.

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the building with the tower now looks like this, and (although i am no expert at dating late-Victorian architecture) it seems entirely possible that it was standing in this place by 1887.

Screenshot2013-04-05at93421PM_zps50aa8d4b.png:original
 
I noticed on the map above that St. Joseph's Convent is indicated where the present-day hospital is, and did some looking into the history of the site -

Sunnyside Villa, 1859
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Sacred Heart Orphanage, 1907
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Sacred Heart Orphanage, 1911
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St. Joseph's Hospital, 1930
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You can still see the first phase of the hospital building (shown above) from the Queensway - it's been retained, albeit tucked neatly within the larger complex.
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While not in the news much today, the Sister's of St. Joseph made a number of interesting contributions to the city fabric, first downtown and subsequently in the former suburbs, throughout the early to mid-twentieth century.
 
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Funny how many of Toronto's hospitals are a miss-mash of buildings from various generations somehow integrated into one.
 
While not in the news much today, the Sister's of St. Joseph made a number of interesting contributions to the city fabric, first downtown and subsequently in the former suburbs, throughout the early to mid-twentieth century.

Including the site of Provincial office complex at Wellesley and Bay, once home to the Mother House (and St. Joseph's School is still across the street):

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Nuns on Bay Street:

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