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Leaside (/'liːˌsaɪd/) is a neighbourhood in Toronto, Ontario, Canada. It is located northeast of Downtown Toronto, in the vicinity of Eglinton Avenue East and Bayview Avenue. The area takes its name from William Lea and the Lea family, who settled there in the early years of the 19th century. The area first developed as farmland along with Toronto through the 19th century. It was incorporated as a town in 1913. In 1967, it amalgamated with the township of East York to form the borough of East York. In 1998, it became part of the city of Toronto. It is one of the most expensive and exclusive neighbourhoods in the city.

The general area of Toronto had been inhabited by various First Nations at least as early as 3000 BCE, when the Laurentian peoples moved south into the area just east of Toronto. The first European known to travel to the area was Étienne Brûlé, who passed through the area in the early part of the 17th century. Surveying by Europeans began in earnest in the 1780s, with people fleeing the American Revolution. John Lea Sr. was born in 1773 in Lancashire and immigrated to York, Upper Canada in 1819, coming from Philadelphia in the United States where they immigrated to in 1818. Before immigrating, he married Mary Hutchison (born in Cumberland) and they had their first child in Lanchester on May 28, 1814 and named him William Lea. John Lea Sr. had three children William, John Jr. and Mary. In 1851, William Lea bought land just south of his father's farm, and began constructing a large, octagonal brick house, which he named "Leaside". The house was completed in 1854, the same year John Lea Sr. died, aged 81. The building served not only as a home and court house for William Lea's family, but after he became a Magistrate in the County of York, soon served as a residence, a town hall and a post office as well. The property became the possession of William's eldest son Joseph upon his death in 1893. Joseph lived in the octagonal house until 1903. Afterwards, it was abandoned and later demolished by the Canadian Northern Railway in 1913. The company later set fire to the old landmark in order to clear the land to make way for the company's proposed sidings and townsite. In the 1870s, the Ontario and Quebec Railway Company purchased a few acres (hectares) of land on the south east corner of William Lea's property to run its railway across. The Ontario and Quebec Railway Company encountered financial difficulties in 1884, and leased part of its railway, including the section of track running through Leaside, to the Canadian Pacific Railway for 999 years. The Canadian Pacific Railway decided to establish a maintenance stop and a sliding by pass on the railway on the land purchased from William Lea, which was considered attractive because it was uniformly flat. The station was completed in September 1894 and named "Leaside" in honour of William Lea.

In 1912, William Mackenzie and Donald Mann, the owners of the Canadian Northern Railway, hired landscape architect Frederick Todd to plan development for a community to be built around a maintenance yard for their railway, which ran beside the CP lines through the Leaside area. Mackenzie and Todd founded the York Land Company to purchase land for such a town. The company purchased over , including most of the third concession and some land north of Eglinton Avenue. The town of Leaside was planned by Todd for the company, which put its name to many of the local streets; Laird Drive, Hanna Road, and Wicksteed Avenue all bear the name of Canadian Northern Railway company executives. A similar request to the city of Toronto was met with a similar reply. With their attempts to include Leaside within another city or town rebuffed, Colonel Davidson and Randolph McRae applied to the province of Ontario to incorporate Leaside as a town. The Town of Leaside was officially incorporated on April 23, 1913. The population of Leaside was 43. A town council for Leaside was elected on May 8, 1913 In addition to the new factory, Canada Wire and Cable moved their other Toronto production plants to the same location to increase efficiency. Canada Wire and Cable also created the subsidiary company Leaside Munitions Company to oversee shell production. While the industrial development in the area went ahead as planned during World War One, the anticipated residential development did not occur. As late as 1929 the population remained under 500. World War I spurred the demand for industrial output but diminished the call for new housing. The bankruptcy of Canadian Northern Railway left the project at a loss and Leaside's isolated location made it unappealing to workers from Toronto.

After the war, the strip became the site of Canada's first delivery of airmail on June 18, 1918, when pilot Brian Peck delivered 120 letters from Montreal, Quebec. However, at this time Leaside stood on the edge of Toronto and was increasingly an appealing place for investment. Investors from Baltimore bought property that had previously belonged to Robert T. Davies for the construction of a race track. They formed the Thorncliffe Park Racing and Breeding Association Ltd. to operate the track. At the onset of the Great Depression, the Durant Motor Company ran into financial troubles. The last cars were produced in 1933, and the buildings were occupied by the Canada Wire and Cable company. At the start of World War II, Lincoln Electric moved their operations to Leaside industrial park, adjacent to the Canada Wire and Cable plant. The new location, constructed in 1940, covered On July 16, 1940, Research Enterprises Limited was incorporated. The company operated only during the war, closing in 1946. It was, however, the largest single employer in Leaside's history, employing over 7500 men and women at its peak. The site manufactured military radio equipment and optical supplies, with a total value of $220 million (CDN) in goods produced during the war. As part of a Royal Canadian Air Force public relations plan, the town of Leaside officially "adopted" No. 432 Squadron RCAF of No. 6 Group RCAF. Formed and adopted on 1 May 1943, the squadron took the town's name as its nickname, becoming 432 "Leaside" squadron RCAF. The sponsorship lasted the duration of the war. In 1945, at the end of World War II, the population of Leaside stood at 9,800. In 1949, Leaside's population had grown to 14,826. The site was previously a marsh where people dug loam for their gardens. Investors from Toronto bought the racetrack that year. The rapid growth of Thorncliffe in the 1950s necessitated the construction of a second north–south bridge across the Don Valley. In 1955, Leaside's population had grown to 16,779 to form the borough of East York. As such Leaside became a neighbourhood within East York. Passenger train service to Leaside Station ended in 1970, and the station was closed. The station would reopen briefly in the 1980s as a restaurant, but would see no further passenger traffic. Leaside Airport fell into disuse, and in 1971 the last hangar was demolished. Canada Wire and Cable was purchased by Alcatel in 1991, and the operations relocated to Markham in 1996, with the location being converted to a shopping centre. The plant had expanded through the years and been a major influence in Leaside, employing over 2700 workers at its peak. It had also been a strong influence over the community in other ways, investing in the community in various ways, including the construction of a water main in 1918. East York merged with five other municipalities in 1998 to form the new City of Toronto.

Leaside lies on the Iroquois Plain. The actions of the glacial Lake Iroquois made the Leaside area into a flat plateau, surrounded on three sides by deep river valleys.

Leaside is made up predominantly of single family homes housing upper middle class families. The most famous house in Leaside is James Lea's, located at 201 Sutherland Drive. Built in 1909, it is unique in that the back of the house faces Sutherland Drive. It was originally built to face a street that no longer exists.

The largest recreation centre in Leaside is Leaside Memorial Community Gardens which includes an indoor swimming pool, two ice rinks, a curling rink, and a large auditorium. Serena Gundy Park is in the north east corner of Leaside. The park covers which are generally in a natural state. The park is used for picnicking and hiking in the summer and cross country skiing in the winter. The park is also connected by walking paths to Sunnybrook Park. Trace Manes Park is in south Leaside. Howard Talbot park in south west Leaside features two baseball diamonds.

Northlea Elementary and Middle School is located on the site of the old Divadale Estate on Rumsey Road north of Eglinton Avenue. It was opened in 1944 and had 15 classrooms. In 1991–93, the school underwent extensive renovations and the school now educates over 800 students. The renovation provided additional classroom space to the school as well as a new library, and second gymnasium. The playing field is artificial turf. The school is operated by the Toronto District School Board. Northlea is a dual track school offering regular English programs from Junior Kindergarten to Grade 8, and French Immersion programs from Senior Kindergarten to Grade 8. Northlea welcomes commuters for the impressive French Immersion programs. Bessborough Elementary and Middle School, located close to Leaside High School in South Leaside, has offered education to those living in the older part of Leaside. St. Anselm Catholic School, also located on Bessborough Drive, opened in 1939 and presently has an enrollment of 340 students from Junior Kindergarten to Grade 8. Rolph Road Elementary School, an elementary school for junior kindergarten to grade 6, is the other elementary school in the neighbourhood. Located on Rolph Road, it is in South Leaside and is a feeder school to Bessborough. Leaside High School began on the top floor of Rolph Road School in 1945. The "new" high school opened in September 1948 and welcomed back local students who had been attending Lawrence Park and Jarvis Collegiate. Along with the growth of these schools in the 1940s and 1950s, the growing population of Leaside also supported one of North Toronto's first preschools. Sunnybrook School was founded in 1952 in the basement of St. Augustine of Canterbury Church in Leaside. In 1960 the school moved to its present 469 Merton Street location, just west of Leaside in Davisville. In addition to the Toronto District School Board, three other public school boards also operate in the city. The Toronto Catholic District School Board (TCDSB), is a public English separate school board; Conseil scolaire Viamonde is a secular French public school board; and the Conseil scolaire de district catholique Centre Sud is a French separate public school board. However, the French school boards do not operate a school in the Leaside neighbourhood. St. Anselm Catholic School is a coeducational, Catholic, elementary school in the south of Toronto, Ontario. It was named after the philosopher and theologian of Canterbury, Saint Anselm. It was established in 1939, with only 2 classrooms under principal Mary Breen. Additions to the school were made in 1943, 1947 and 1951. The library and gymnasium were added in 1966. Today the school serves students from Kindergarten to 8th grade. In 1997, the MSSB/TCDSB made funds for the school to be a two story building. When the school was being renovated, the students were moved to 1107 Avenue Road, which is now Marshall McLuhan. The students came back to the newly renovated school in 1998. Bloorview School Authority is an educational facility physically located within the Holland Bloorview Kids Rehabilitation Hospital in north Leaside, although they are each separate legal entities. The Bloorview School Authority offers various educational programs for children, some of whom are patients in the hospital. Included in the offerings is a full day program for children from junior kindergarten to grade one, based on Ontario school curriculum.

The first town council for Leaside was elected on May 8, 1913. In 1967, Leaside was amalgamated with the township of East York to form the borough of East York, from this point forward Leaside was a community within East York, and governed by the municipal council of East York. Amalgamation was opposed by Leaside residents fearing residential tax increases and the loss of the Leaside community identity. Taxes in Leaside were lower than the surrounding regions as residential taxes in Leaside were subsidized by those from industrial areas; residential taxes climbed in Leaside every year from 1967 to 1972. Beth Nealson, the last mayor of Leaside ran against True Davidson (the reeve of East York) for mayor of the amalgamated borough. Nealson lost to Davidson. In 1998, East York (including Leaside) was amalgamated with the City of Toronto to form the City of Toronto, from this point forward Leaside was a community within Toronto, and governed by the municipal council of Toronto. Parker lost the seat to Burnside by a margin of 3,248 votes.