Darlinghurst Gaol
Darlinghurst Gaol, the large sandstone penal complex in the middle of Darlinghurst was built between 1836 and 1840. The large sandstone walls still bear convict markings, and the complex features six wings surrounding a circular chapel. Australian poet Henry Lawson spent time incarcerated here during some of the turbulent years of his life. The site is now open to the public as the National Art School. The last hanging at the gaol was in 1907 (Jahn, 1997).

Darlinghurst Courthouse
Darlinghurst Courthouse is an imposing sandstone building on Taylor Square. It was designed by architect Mortimer Lewis (1796 - 1879) in 1844, and has a Greek Revival style facade. The central block is adapted from an 1823 design in Peter Nicholson's 'The New Practical Builder' (Apperly, Irving & Reynolds, 1989).

Darlinghurst Fire Station
Completed in 1912, this three-storey brick and stone building occupies a prominent location at the corner of Darlinghurst Road and Victoria Street. It was designed in 1910 by Walter Liberty Vernon (Jahn, 1997). It still functions as a fire station and is listed on the Register of the National Estate.