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Located in Sydney's upper north shore, Cheltenham was initially the land of the Guringai Aboriginal people with white settlement in the area dating back to the mid 1800s. Cheltenham takes its name from a house built by William Chorley who was one of the area’s first land owners, naming his house Cheltenham after his hometown in Gloucestershire. The fertile lands and relatively small land grants of Cheltenham were originally utilised by settlers for orchards and other small pastoral pursuits.
With the railway line extended through the area in the late 1800s, the suburb's English heritage saw it take on a distinctly English village feel with grand mansions constructed around the railway line by Sydney's elite. Unlike other suburbs located alongside railway stations on Sydney's north shore, a shopping strip did not form alongside the station as the area was surveyed for residential development only with no township accounted for in the plans. This continued into the redevelopment boom following World War II in the 1940s with Cheltenham Girls High School the only prominent non-residential development in the area.
Cheltenham Girls High School is a comprehensive state school which was established in the late 1950s on land donated by the Vicar to the state with the provision that it be used to build an educational facility. The school’s first principal Bessie Mitchell has been recognised as one of Australia's finest educators receiving an MBE for her work in 1971 and her legacy remains alive today with the school still considered as one of Sydney's best girls schools.
Today, many families live in the picturesque suburb which remains mainly residential.