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Last Update: August 1 2017

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York Square
photo credit, courtesy of Richard Longley

At risk status:
This building is at risk

Redevelopment Proposal could destroy essence of early Diamond and Myers project

Additional Images:

Name & Location
York Square
148 Yorkville Avenue
Bloor-Yorkville, Toronto

Alternate names:
33-39 Avenue Road

At a time when urban renewal was the norm, this project was the first to incorporate older fabric into a new project. Designed by the new firm, Diamond and Myers, it set a new approach for marrying new and old in Toronto and around the world, Published internationally, in the U.S, Japan, and Europe, receiving 8 pages in Progressive Architecture. This complex was a finalist for a Massey Medal for Architecture in 1970. It is currently the subject of a redevelopment application, for a high rise condominium, by architects Zeidler Partnership, which proposes to save only the elevation at the corner of Avenue Road and Yorkville Avenue. Over 75% of the designated heritage attributes are destroyed, and what is left is ridiculed by the scale of the proposal. The building was designated in 2014.


Year Completed:


The following companies are associated with this building
  • Architect - Jack Diamond & Barton Myers
  • Developer - I.R. Wookey


Shopping centre

Current use:

Heritage property



  1. York Square in Toronto
    Author - Baumeister 69
    Date - October 1972
    Document - York Square in Toronto

  2. Toronto Architecture: A City Guide
    Author - Patricia McHugh
    Page - 203

  3. Toronto Star
    Author - Christopher Hume
    Date - July 15, 1992
    Page - B2
    Notes - Mentions this complex in book review.

  4. City of Toronto Designation Report
    Date - January, 2014
    More information

  5. Development Proposal
    Author - Empire Communities
    Date - 2015
    More information

  6. Urban Toronto New Proposal
    Date - February 10, 2016
    Notes - Most Recent Proposal
    More information

  7. Planning Application to City of Toronto, submitted February 2016
    Date - February 2016
    Notes - Link to City of Toronto website where application for redevelopment is posted. Includes plans, perspectives, elevations, heritage report, designation report.
    More information

  8. Looks like time´s up for Yorkville´s old guard
    Author - Globe and Mail, John Bentley Mays
    Date - June 13, 2013
    Notes - In the summer of 1969, when I moved from the United States to Toronto, the intoxicating haze of rock music, incense, pot fumes and flower-power politics hung heavy over the little Victorian streets of the Yorkville district. Head shops and vintage clot
    More information

  9. York Square Toronto
    Author - The Canadian Architect
    Date - June 1969
    Page - 36-38
    Document - York Square Toronto

  10. York Square
    Author - William P. Kilbourn
    Date - 1986
    Page - 297-98
    Notes - Found in Toronto Observed: Its Architecture, Patrons and History, Oxford University Press
    Document - York Square

  11. Inventory of Heritage Properties
    Author - City of Toronto
    More information

  12. Renovation urbane: Renovation de York Square, Toronto, Canada
    Author - L’Architecture d´ Aujourd’hui Vol.169
    Date - October, 1973
    Page - 47-53
    Document - Renovation urbane: Renovation de York Square, Toronto, Canada

  13. Urban Supertoy Subdues Renewal Bulldozer
    Author - Progressive Architecture 50
    Date - 1969
    Page - 144-153
    Document - Urban Supertoy Subdues Renewal Bulldozer

  14. Stars, Imports, and Other Phenomena, A reflection on an Aspect of the Evolution of Architectural Culture in Toronto
    Author - George Baird
    Date - 2010
    Notes - Found in the Journal of the Society for the Study of Architecture in Canada (JSSAC) No. 2
    Document - Stars, Imports, and Other Phenomena, A reflection on an Aspect of the Evolution of Architectural Culture in Toronto

  15. Toronto’s Lost Villages
    Author - Ron Brown
    Date - 1997
    Page - 60-63
    Document - Toronto’s Lost Villages - Yorkville

  16. Preliminary Heritage Impact Assessment For Working Group Discussion
    Author - ERA Architects Inc.
    Date - August 27, 2014
    Document - Preliminary Heritage Impact Assessment For Working Group Discussion

  17. Toronto 1970 Design Awards
    Author - Architecture Canada RAIC/IRAC
    Date - April 13 1970
    Page - 535
    Document - Toronto 1970 Design Awards

  18. York Square Resources Package 1
    Author - ACO Toronto
    Date - 2016
    Notes - Press Materials from the time of the original construction. Can be viewed or downloaded from Google docs, very large file.
    More information

  19. Press Publications from 1968-70
    Author - Several
    Date - 1968-1970
    Notes - Compiled by ACO Toronto in 2016
    Document - York Square Resources: International Press Publications

  20. Globe and Mail: Stollery’s is going. But Toronto should do more to save its heritage
    Author - Alex Bozikovic
    Date - January 23, 2015
    Notes - Discusses the reasons for saving what he calls the anti-tower project "Toronto architects have been working on this sort of pairing since the 1960s. In those days, “urban renewal” meant levelling blocks and building isolated new towers; local urbanist
    More information

  21. York Square Resources Package 1
    Author - Assembled by ACO Toronto
    Notes - A document compiling the various applications and reports that are before the City and the Ontario Municipal Board as of summer of 2016.
    Document - 1d32f68508fcc9b1ce9452a776343dd1.pdf

  22. Architecture and Urbanism
    Notes - Volume 1, Number 11 The article is in Japanese, so additional information (such as author, date, and pages) cannot be translated.
    Document - York Square - Architecture and Urbanism

  23. Scanned Photos and Magazine Articles at Higher Resolution
    Author - uploaded by Lindsay Wu
    Date - August 1, 2017
    Notes - These are photos and scanned magazine pages that have been uploaded to Google Drive
    More information


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