Woolooware is a suburb in southern Sydney, in the state of New South Wales, Australia. Woolooware is located 24 kilometres (15 mi) south of the Sydney central business district in the Sutherland Shire. It shares the 2230 postcode with Cronulla.

Woolooware stretches from Woolooware Bay in the north on the Georges River estuary to Burraneer Bay and Gunnamatta Bay in the south on the Hacking River and Port Hacking estuary. It borders the suburbs of Cronulla, Caringbah, Burraneer and Kurnell.

Woolooware is derived from the Aboriginal word Wooloowa, meaning muddy track. It echoes the area's natural low lying mud flats, salt marsh and once dominant tea tree and black wattle scrub.

It was originally a thickly forested area with tea tree, black wattle scrub and mangrove swamps around Woolooware Bay, and was originally owned by the Dharawal and Tharawal peoples. Those were later reclaimed to create parks and playing fields including Endeavour Field, Woolooware Golf Course and Cronulla Golf Course. 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.

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.

In the 2021 census, there were 5,060 people in Woolooware, 79.7% of whom were born in Australia. The next most common country of birth was England at 4.1%. 87.3% of people spoke only English at home. The most common responses for religion were No Religion 36.9%, Catholic 27.7%, and Anglican 16.2%.

A small group of shops, known locally as Woolooware North, is located on Wills Road, close to Woolooware railway station. Shops include a general store, beauty salon, liquor shop, hairdressers, gift shop, cafe, doctor's surgery and Chinese restaurant. Another small group of shops, known locally as Woolooware South, is located around the intersection of Burraneer Bay Road and Woolooware Road. These shops, include a fish and chip shop, restaurant, chemist, bakery and general store. A petrol station is also located nearby.

Woolooware railway station is on the Cronulla branch line of the Sydney Trains Eastern Suburbs & Illawarra Line or T4 line. The station, like all NSW metropolitan and intercity train stations, is Opal active. All services are double deck electric trains of eight carriages traveling to Bondi Junction stopping at major interchange stations such as Sutherland, Wolli Creek, Sydenham and Central. The station has two platforms and electronic indicator boards.