At the time of its incorporation in 1864, it had the distinction of being the smallest municipality in the Sydney metropolitan area, at a mere 44 acres.

[3] The first Aboriginal inhabitants of Darlington were the Cadigal people of the Eora belonging to the wider Dharug language group.

[4] The Cadigal were a coastal people who subsisted on fishing, hunting land animals and gathering shellfish and plants.

[8] By 1844, the Hutchinson estate, much of Shepherd's Nursery and a portion of the adjoining 96 acre land grant to William Chippendale comprised much of present-day Darlington.

This resulted, despite increasing community opposition and resentment, in the demolition of about 650 houses as well as shops, factories, banks, the post office, the Town Hall and other amenities, and the population of Darlington decreased by about 2,000.

Charles Kernan Reserve on Abercrombie St is named after a former local resident and has playground facilities, public BBQs and a community garden.

The opening of the Eveleigh Railway Workshops in the 1880s was the major stimulus for the building of Victorian worker's terraces in Darlington.

The former factory also represents the historical development of the labour movement as the site of large strikes in 1935 protesting the replacement of skilled with unskilled workers.

The construction of the garage to house delivery trucks for the former IXL jam factory also represents technological advancements of the inter-war period through the growing use of motor vehicles for the distribution of products.

The nucleus of the villa remains highly intact, encapsulated within the walls of St Michael's College, which was built in 1929.

It is a two-storey Gothic Revival style building constructed of polychromatic brickwork, with a spire and a slate roof.

It was built with multiple green glass facades and panels of different colors, types and styles covering different sides of the building.

It features a large outdoor plaza with tiered seating, function space and cafes, interesting architectural themes and dynamic use of building materials.

[citation needed] Sydney University Sports and Aquatic Centre features swimming, tennis, basketball, gymnasium facilities.

[33] Prince Alfred Park is located on Cleveland Street and has tennis, basketball and a newly refurbished swimming pool.

[36] Tin Sheds Gallery on City Road is a contemporary exhibition space located within the Faculty of Architecture, Design and Planning at the University of Sydney.