[citation needed] When European settlers arrived in 1788, First Fleet officer Daniel Southwell translated the local Aboriginal word (Dharug language) Woo-la-ra (also later spelt by others as Willarra and Wallara) as meaning "lookout", but it has also been translated as "camp" or "meeting ground".

[2][3] The name was adopted by Daniel Cooper (1821–1902), the first speaker of the legislative assembly of New South Wales, when he laid the foundations of Woollahra House in 1856.

[4] Although Woollahra is predominantly a residential and retail area today, for over forty years and into early 20th century, there was a large iron foundry and cooking stove factory on Edgecliff Road.

[5] Woollahra was the home of John McGarvie Smith, a metallurgist and biochemist who produced the first preservable anthrax vaccine.

[12] The Congregational Church, on the corner of Jersey Road and Moncur Street, was built in 1875-77 and designed by Benjamin Backhouse.

[13] Woollahra is a considerably affluent suburb, due in part to its proximity to the city and the shopping centre at Bondi Junction, plus a wide range of picturesque homes, mostly in various Victorian styles.

Most of the suburb's housing stock exists in the form of medium or high-density dwelling, as opposed to more high-rise centred regions like Zetland.

The 352 on Oxford Street provides commuters with a service to Surry Hills, Newtown and eventually Marrickville Metro in the city's south.

The nearest railway stations are Edgecliff to the north of the suburb and Bondi Junction to the south, both on the Illawarra line.

Initially a community fair, it grew and became more commercial until local residents became unhappy with its noise, size, and disruption.