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Architectural Conservancy Ontario

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Architectural Conservancy Ontario

The past. Our present. Your future.

York Square

LAST UPDATE: August 25 2020

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photo credit, courtesy of Richard Longley

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, 2018 OMB decision has given permission to destroy all but the front facade. More recent (2020) design retains none of the existing buildings or courtyard. 

Name & Location
York Square
148 Yorkville Avenue
Annex, Toronto


1970: Massey Medal for Architecture

  • Finalist.

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. OMB Case Number PL150988, 

Spring 2020 saw a new design for a 29 story tower by a new developer which retained none of York Square


Year Completed:

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The following companies are associated with this building

Shopping centre

Current use:

Designated under Part IV Ontario Heritage Act



  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

  24. A Toast to the Summer of Love
    Author - Ibrahim Khider,
    Date - September 2017
    Notes -  
    A brief documentary on the Village of Yorkville, Toronto during the Summer of Love in 1967. Also, a piece of property within Yorkville redeveloped during the late 1960´s called ´York Square´. Then-emerging architect, Jack Diamond, chose to hono
    More information

  25. York Square Video-2020
    Author - Old Toronto-ACO Toronto
    Date - August 2020
    Notes - York Square video, produced by Old Toronto for ACO Toronto. The video is 17 minutes long and gives the history of York Square, its international significance, the cultural context of Yorkville at the time of development, including some wonderful footage of Yorkville in the late 1960´s, music, politics and political action to close the street. It also deals with the tax forces that forced closure and sale for redevelopment. 
    More information

  26. City of Toronto Development Application Documents 2020
    Author - Various,
    Notes - All of the background documents for the 2020 development application including the Heritage Impact Assessment by ERA Architecture with justification for complete removal of all identified heritage attributes.
    More information

  27. Heritage impact Assessment
    Author - ERA Architects Inc.
    Date - March 10, 2020
    Notes - This report has been prepared for 140 Yorkville Corporation and considers the redevelopment of the properties at 33-45 Avenue Road and 136-148 Yorkville Avenue (the “Site”). It assesses the impact of the proposed development on the heritage resources on and adjacent to the Site. The Site is comprised of several buildings and an interior public square, which make up a commercial complex known as York Square.
    Document - Heritage impact Assessment


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