Woolloomooloo is in a low-lying, former docklands area at the head of Woolloomooloo Bay, on Sydney Harbour.

Woolloomooloo was originally a working-class district of Sydney and has only recently changed with gentrification of the inner city areas of Sydney. The redevelopment of the waterfront, particularly the construction of the housing development on the Finger Wharf, has caused major change. Areas of public housing still exist in the suburb.

Notable residents are Russell Crowe an actor, Delta Goodrem, a singer and John Laws a former radio presenter on Sydney’s 2UE.

The El Alamein Memorial Fountain is a spectacular fountain and outstanding work of modernist design in water which has been copied all over the world. It has been described as looking like a blown thistle. Throughout the decades of the 1960s and 1970s it was an icon of Sydney, rivalling the Sydney Harbour Bridge and the Sydney Opera House for the frequency with which it was represented in tourism imagery. Aesthetically it is rare in NSW as a local adaptation of the organic school of Scandinavian architectural design and as an example of the application of modernist design technology to fountain design.

Elizabeth Bay House is one of the most sophisticated works of architecture of the early 19th century in New South Wales. Elizabeth Bay House’s incomplete state reflects the 1840s depression which devastated a class of prominent colonial civil servants, pastoralists and merchants. The house is significant for its association with the history of the intellectual life of NSW in the areas of scientific (natural history, particularly entomology, botany) and an aesthetic endeavour through its association with three generations of Macleay family.

Lindesay is a heritage-listed former residence designed by James Chadley and Edward Hallen (attributed), with Francis Clarke and Robertson & Marks (the service wing) and it was built from 1834 to 1836. The property is owned by the National Trust of Australia (NSW). It was added to the New South Wales State Heritage Register on 2 April 1999. Lindesay was the first major house to be constructed on Darling Point and is aesthetically important as the earliest example of the domestic Gothic Revival style in Sydney. Some of its residents were colourful figures who played an important part in the history of New South Wales, such as C.D. Riddell, Sir Thomas Mitchell, Sir Charles Nicholson, William Bradley and John Macintosh.

Redleaf is one of the few mid-nineteenth century grand mansions, which once dominated the prominent harbour foreshore sites in Sydney that still survives. The intactness of this original 1860s harbourside estate with its mansion, its former stables, grounds and setting (including harbourside frontage) make it a rare survivor in the Sydney region.

The suburb was named after the Right Honourable George Rose (1744-1818), the Joint Secretary to the Treasury in England who played an important part in the establishment of the colony in Governor Arthur Phillip’s time whilst also being a friend and mentor. George Rose is remembered by the two Sydney place names, Rose Bay and Rose Hill.

From 1938, seaplane flights to and from London began and terminated in Sydney Harbour on Rose Bay, making it Sydney’s first international airport, and what is now Rose Bay Water Airport.