The suburb of Woolooware is probably named after Woolooware Bay. This notation was first used on Assistant Surveyor Robert Dixon's map of 1827.
The land was at one time granted to John Connell and was later acquired by Thomas Holt who established his Sutherland Estate in the 1860s.
The first "road" put down in the Shire was an "access road" in 1842; from the west shore of Botany Bay, across the low swampy land adjoining, to approximately the present site of Burraneer Bay Rd.; but of course, was little more than a rough bullock track. John Connell (son of the first John Connell) was then working the big timber which covered most of the Shire 130 years ago. To provide access for his timber, he cut a canal from the-water's edge to the foot of the Woolooware track about 800M long. The canal was about 6M wide and at ugh tide over 1M deep, sufficient to allow the timber to be floated out into the George's River, where it was probably rafted across to Rocky Point Rd. and so transported by bullock dray to Sydney or by coastal ships sailing through Botany Bay Heads. Connell also constructed here a sawpit and a rough wharf. The logs being crosscut in the pit before shipping. After the Holt takeover of most of Connell's land, Holt leased out these timber concessions until about 1880. After this, the canal site became a popular rendezvous for Botany Bay fishermen, who used the Woolooware Rd. as a kind of "portage" to enable them to cross over to Gunnamatta and Port Hacking River to fish. Connell's canal was for many years affectionately known as “The Drain". Until about the end of World War 2 the remains of the old canal could still be seen, as also the slide-down to the canal for the timber. Some time ago, the Cronulla Golf Club took over much of this swampy area to reclaim for extensions and with the construction of the Captain Cook Drive, most of this old site has gone. Check out GC5K01X, "Connell's Canal" has now passed into local history.
Mostly rural in character with some remnant eucalypt forest the Woolooware area was taken up by families such as the Greens and the Newports who operated dairies from the 1920s. Greens dairy became part of what is now the present day golf course. Other local industry included Burrell's laundry which was a commercial service operating in the 1940s with both the army and railway as clients.
Woolooware Bay also had a long history of oyster farming but came to an end as a result of residential development causing poor water quality.
After the extension of the railway line from Sutherland to Cronulla in 1939 and the end of World War Two, the area attracted mostly residential settlement. It was originally a thickly forested area, with mangrove swamps around Woolooware Bay. Those were later reclaimed to create parks and playing fields including Endeavour Field, Woolooware Golf Course and Cronulla Golf Course where native ducks live. Click here to access the Jigidi puzzle. The area was subdivided after the railway line from Sutherland to Cronulla was opened in 1939. The first public school opened in 1951 and the post office opened in October 1954. A high school was opened in 1968.
A pencil drawing of WOOLOOWARE HOUSE, one of a series by internationally acclaimed artist and designer IAN GALBRAITH. Ian's works have featured in important art exhibitions around the world and many have been purchased for famous private collections. WOOLOOWARE HOUSE, formerly known as 'Panorama' is an Edwardian style building thought to have been built about 1910. This is supported by the design of the timber scrollwork on the veranda beam, the stonework splayed pedestals of the veranda posts, the casement glazing bars and the leadlight glazing to the facade joinery and the exterior door panelling. The building is listed in the local Heritage Register.
The Australian division of Taylor Woodrow, a British construction company, built the first subdivision with project homes in Australia in north Woolooware, including the classic red brick homes in Taywood Street.