Notice of Intention to Designate a Property - 357 Simcoe St. S.

Take notice that the Council of The Corporation of the City of Oshawa intends to designate the following property of cultural heritage value or interest pursuant to the provisions of Part IV of the Ontario Heritage Act, R.S.O. 1990, Chapter O.18:

357 Simcoe Street South
[legally described as PIN 16370-0343 (LT) PT LT C11 SHEET 20 PL 335 OSHAWA AS IN D140091; SUBJECT TO AN EASEMENT AS IN DR2256989; CITY OF OSHAWA, PIN 16370-0344 (LT) PT LT C11 SHEET 20 PL 335 OSHAWA PARTS 1, 2 & 3 40R18657; SUBJECT TO AN EASEMENT AS IN DR2256989; CITY OF OSHAWA, and PIN 16370-0348 (LT) PT LT C11 SHEET 20 PL 335 OSHAWA PTS 4 & 12, 40R18657; T/W D535023; S/T D535026; SUBJECT TO AN EASEMENT AS IN DR2256989; CITY OF OSHAWA]

The property at 357 Simcoe Street South, formally known as the Holy Cross Catholic School, is located on the east side of Simcoe Street South, north of Fisher Street and south of Olive Avenue, in the southern portion of the City of Oshawa. The subject property consists of the original two-storey red brick building that was initially built in 1938 as a rear addition to the former Cowan mansion (demolished in 1952), a subsequent front addition built in 1952 in place of the former mansion facing Simcoe Street South, two annexes at the rear of the site constructed in 1955 and 1963 as a connected structure, separate from the 1938 and 1952 structures, and a final addition (former gym and library) built in 1973 that connected the annexes to the 1938 and 1952 structure.

The two annexes at the rear of the site constructed in 1955 and 1963 and the final addition (former gym and library) built in 1973 do not possess cultural heritage value or contain heritage attributes.

Statement of Cultural Heritage Value or Interest

357 Simcoe Street South has design value as a representative example of a former educational building influenced by the Beaux-Arts architectural style. Its legibility as a former school is expressed in the two-storey massing, which includes the original 1938 section (rear) and the c. 1952 addition (façade). The street facing section follows a rectangular plan with flat roof and red brick construction laid in a common bond design. The side elevations showcase decorative brickwork which creates a large cross. The Beaux-Arts influence is legible on the balanced and symmetrical façade which includes a prominent two-storey frontispiece flanked by groupings of large windows with solid surrounds. Specifically, the main level of the frontispiece includes a rectangular entrance opening with double doors and a large rectangular transom which is topped with decorative concrete banding with dentils and framed with smooth concrete. There is a decorative symbol (a Chi Rho) etched into the concrete above the entrance. The upper level of the frontispiece has decorative metal banding and is topped by a concrete parapet with “Holy Cross” etched into the design. The large rectangular window openings, arranged in groups of three, are framed by large concrete columns which extend from the 1st to 2nd storey and create vertical emphasis which reinforces the rhythmic window arrangement. There is a simple rectangular concrete square located at the bottom of each of the columns of windows.

The rear two-storey section with recessed portions showcases a large rectangular entrance on the south elevation which is topped by a three-paned segmentally arched transom accented by large panelled concrete voussoirs with a cross etched into the keystone. This section also has red brick construction; however, the brick design includes a row of Flemish bond separated by five stretcher courses. The rectangular window openings are topped by a large concrete lintel and lug sills. Overall, the subject building exhibits decorative elements which are common features of schools built with Beaux Arts influences.

357 Simcoe Street South has associative value for serving the educational needs of the surrounding Catholic community from 1938 until 2008. In 1937, the Roman Catholic Diocese of Toronto purchased the lands associated with 357 Simcoe Street South from Frederick W. Cowan, the son of prominent Oshawa industrialist William F. Cowan, for use as a Catholic School for Oshawa’s south end. The former Cowan mansion was initially used as a chapel with two classrooms, but an eight-room addition was built at the rear of the mansion in 1938 shortly after its purchase. When the Holy Cross Roman Catholic Church was opened on the adjacent lot, the mansion was refurbished to accommodate additional classrooms. However, it was demolished around 1952 and a new building with eight classrooms was added, connected to the above noted 1938 structure. This new addition was in response to the area’s population growth through the mid-20th century, in part from an increase in immigration from countries such as Italy, Ukraine, and Poland. By the end of World War II, the enrollment at Holy Cross was approximately 900 students which necessitated the construction of the new building in 1952 and eventually two annexes (c. 1955 and 1963), and a library and a gym (c. 1973) were added. With the opening of other schools in the area, a French immersion program was added in 1990 to increase enrollment. However, by 1994, student enrollment had dropped to an all-time low, and the school ceased operation and was sold in 2008. Today, the subject property continues to serve the community with the recent establishment of an outreach centre for at-risk and homeless youth and offers affordable housing for underserved youth.

357 Simcoe Street South, formally known as the Holy Cross Catholic School, is historically linked to the Holy Cross Parish (Holy Cross Roman Catholic Church) which is located directly south on the adjacent lot at 373 Simcoe Street South. Both of these important institutions were established and operated by the Roman Catholic Diocese of Toronto to serve the needs of the surrounding community. The subject property was purchased from the Cowan family by the Roman Catholic Diocese of Toronto in 1937 and the existing Cowan residence was immediately converted into a chapel and two classrooms, serving the spiritual and educational needs of the community. One year later, eight more classrooms were built connected to the rear of the original Cowan residence with teaching being carried out by the sisters from the order of St. Joseph. Eventually, a separate church was constructed at 373 Simcoe Street South, which continues to operate as the Holy Cross Parish. The Holy Cross Secondary School operated until 2008 but still bears the name ‘Holy Cross’ on the façade.

On the basis of the cultural heritage value or interest outlined above, the property at 357 Simcoe Street South meets the criteria for designation under Part IV of the Ontario Heritage Act, in accordance with Ontario Regulation 9/06, as amended by Ontario Regulation 569/22 subsection 1(2), specifically criteria 1, 4, and 8.

Heritage Attributes

The following heritage attributes of 357 Simcoe Street South reflect the property’s design and physical value as described in the Statement of Cultural Heritage Value or Interest:

• The two-storey building (street-facing section) constructed in c. 1952 influenced by the Beaux-Arts architectural style with the following features:
  
  
  • Flat roof;
    
    
  • Red brick construction laid in a common bond design;
    
    
  • Decorative brickwork of a large cross on both side elevations;
    
    
  • Balanced and symmetrical façade;
    
    
  • Two-storey frontispiece, specifically:
    
    
    • Main level including the rectangular double door entrance opening with a large rectangular transom topped with decorative concrete banding with dentils and framed with smooth concrete;
      
      
    • Decorative symbols (a Chi Rho) etched into the concrete above the entrance;
      
      
    • Upper level of the frontispiece with decorative metal banding and topped by a concrete parapet with “Holy Cross” etched into the design;
      
      
  • The large rectangular window openings arranged in groups of three; and,  
  • Large concrete columns that frame window openings and rectangular concrete squares located at the bottom of each of the columns of windows.
    
    
• The two-storey building (rear section) constructed in 1938 with the following features:
  
  
  • Flat roof; 
    
    
  • Large rectangular entrance on the south elevation topped by a three-paned segmentally arched transom, accented by large panelled concrete voussoirs with a cross etched into the keystone;
    
    
  • Red brick construction; the brick design includes a row of Flemish bond separated by five stretcher courses; and,
    
    
  • Rectangular window openings topped by a large concrete lintel and lug sills. 

The following heritage attributes of 357 Simcoe Street South reflect the property’s historical and associative value as described in the Statement of Cultural Heritage Value or Interest:

• Two-storey building and its first addition constructed in 1938 and c. 1952, respectively, influenced by the Beaux-Arts architectural style;
  
  
• Location on the east side of Simcoe Street South; and,
  
  
• Orientation, massing and visibility from Simcoe Street South.

The following heritage attributes of 357 Simcoe Street South reflect the property’s contextual value as described in the Statement of Cultural Heritage Value or Interest:

• Location on the east side of Simcoe Street South, adjacent to the Holy Cross Roman Catholic Church;
  
  
• Parapet etched with “Holy Cross”;
  
  
• Religious symbol etched over west elevation entrance; and,
  
  
• Religious symbol etched over south entrance.

The full particulars for the subject property, including heritage attributes to be protected, are available for inspection in Planning Services, 8th Floor, City Hall, 50 Centre Street South, between the hours of 8:30 a.m. and 4:30 p.m., Monday through Friday. If you would like to obtain further details, please contact Harrison Whilsmith, Planner B, at (905) 436-3311 ex. 2697 or by email at hwhilsmith@oshawa.ca.

Any person may, on or before the 31th day of October, 2025, send by registered mail or deliver to the City Clerk, Notice of Objection to the proposed designation, together with a statement of their reasons for the objection and all relevant facts. If a Notice of Objection is received, the Council of the City of Oshawa will consider the objection on or before the 29th day of January, 2026.