Many Cabbagetown youngsters in the late 19th century who were of school age attended Winchester Public School. Named after the famous historical city of Winchester in Hampshire, England, the School’s original parcel of land measuring 280 x 165 feet, was purchased from A.V. DeLaporte on December 20, 1873. The roughcast building was ready for opening by September 1874, at which time Winchester Public School had only two teachers and approximately250 students. Many Cabbagetown youngsters in the late 19th century who were of school age attended Winchester Public School.

Named after the famous historical city of Winchester in Hampshire, England, the parcel of land measuring 280 x 165 feet, was purchased from A.V. DeLaporte on December 20, 1873. The roughcast building was ready for opening by September 1874, at which time Winchester Public School had only two teachers and approximately 250 students. A year later, two additional teachers brought the staff’s total to four teachers. Wood-burning stoves were used at that time to heat the building which, by 1878, was enlarged to eight rooms. At the beginning, Winchester Public School taught: Reading, Spelling, Arithmetic, Writing, Geography, Map Work, Drawing, Music, Grammar and Composition. The level of learning system used back then consisted of “divisions”, as opposed to the system introduced in 1937 of “grades” (still used in today’s school system).

In 1893, the Winchester Street Kindergarten was opened. With an escalating enrollment, the School was enlarged once again in 1898 to 9 rooms. The final purchase of land was made on April 30, 1912, from the Prospect Park Curling & Skating Club and in 1914, the School underwent remodeling. Winchester Public School’s architectural beauty and construction was publicly recognized on May 26, 1917, when W.A. Craick of The Toronto Star Weekly wrote: “… the building has a massive dignity and a good old-modern constructions … the hallways are unusually broad and well-lighted and the ceilings quite exceptionally high.” 1931 marked another year of remodeling for the School, when fire-proof doors were installed along with a dual steel-concrete staircase to accompany the 15-room building. By 1959, necessity prompted the Board’s purchase of properties valued at a total of $379,000 (approx.) in order to construct the Senior Public School building. All went well for Winchester Public School until August of 1973, when the School suffered $400,000 in damages due to a fire which gutted the top floor of the “old” building. Nevertheless, undaunted by the setback, the School celebrated its 100th anniversary in October 1974 with four days of festivities.