Once a desirable bayside address east of central Sydney, the area grew more congested and grimy as the wharves expanded and the boarding houses and pubs gave refuge to larrikin gangs and petty criminals. Though now bisected by freeways and rail it is slowly reclaiming its heritage and character with extensive residential development and sympathetic landscaping.

Woolloomooloo Bay 2008
The Loo


by Shirley Fitzgerald, 2008 Creative Commons License

Woolloomooloo's chequered history includes its past as a Gadigal hunting ground and ceremonial space, its subsequent use for farming and country housing for Sydney's elite, and its evolution into an area of workers cottages and maritime industry. From the 1970s new residents joined with unions and locals to preserve Woolloomooloo from developers.
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Woolloomooloo demographics

Kids & Dogs, Woolloomooloo, Sydney
Woolloomooloo Bay and Elizabeth Bay 2005
View from Woolloomooloo 1857
John Palmer's residence Woolloomooloo House,  c1818
National Opera of Australia singers rehearsing Madama Butterfly at Plunkett Street School, Woolloomooloo  January 1956
The explosion of Mr L'Estrange's balloon near Sydney 15 March 1881
Plan shewing the situation of the allotments for sale at Darlinghurst Elizabeth Bay: the property of Alexr Mcleay Esqre 1840s
Women lay wreaths on the wharf at Woolloomooloo where the WW I troops departed, c1931
Tarmons, Woolloomooloo, residence of Sir Maurice O'Connell 1845
Wolomoloo (Springfield House) 1832
View north from Craigend looking over Woolloomooloo and Port Jackson 1845
Boundary post No 1 - Bourke Street and Plunkett Street 2007
Sketch of the coast from Darling Harbour to Elizabeth Bay: showing the grants to Mr McLeay and six other gentlemen.  Ordered by the House of Commons to be printed, 16th July 1832
Woolloomooloo, Potts Point and Elizabeth Bay 1832
Stairs for pedestrians in Sydney, NSW [Butler Stairs, Woolloomooloo] c1900
Butler Steps between Victoria and Brougham Streets c1888
A Glimpse of Sydney from Darlinghurst c1886
A cliff-face stair-way, Darlinghurst c1886