Few roads in Sydney have changed as much as Darlinghurst Road.

From an exclusive residential street reserved for the elite to a Bohemian wonderland to the vibrant boulevard of today, we explore its fascinating history.

Darlinghurst Road’s beginnings

Situated on Gadigal land, Darlinghurst Road was home to five windmills in the early days of the colony. The road, which runs along a high ridge, was perfectly positioned for the windmills to catch the breeze and grind grain into flour. The last mill stood until around 1873. In these early days, Darlinghurst Road was known variously as Woolloomooloo Road, Wind Mill Hill Road, Mill Hill Road, Mill Road, or simply ‘The Hill’. But once the surrounding area became known as Darlinghurst, the name Darlinghurst Road stuck.

‘Mansion row’

Governor Ralph Darling had chosen the ridgeline of Darlinghurst Road as the site for fine homes for the colony’s elite, and by the 1830s, it was lined with exclusive mansions. One of these was Maramanah, built in the 1840s for shipping merchant Deloitte at the northern end of Darlinghurst Road. The eccentric manor passed through many owners before being commandeered as barracks during the Second World War. It was demolished in 1954 to make way for Fitzroy Gardens and the El Alamein Fountain.

Meanwhile, at the other end of Darlinghurst Road, a new Catholic church – the first for the eastern suburbs – was being planned. Sacred Heart Church was completed in 1852. It was demolished in 1910 to make way for the widening of Oxford Street, with work on a new church commencing in 1911. In the 1950s, Sacred Heart welcomed the wave of post-war migrants to Darlinghurst by conducting services in Spanish and Portuguese.

No longer just for the wealthy

From the 1870s, many of Darlinghurst Road’s grand homes were subdivided and replaced with large Victorian terrace houses, and by the 1880s, boarding houses were common. Darlinghurst Road and its surrounding area were no longer exclusively the province of the well-to-do.

It was during this time that St Vincent’s Hospital opened. The Sisters of Charity-founded institution was set up as a free hospital for the poor on a smaller site on Victoria Street. In 1870, after receiving a Crown Land Grant and public fundraising, they moved into a larger building on the current site. Today, St Vincent’s, which incorporates the Sacred Heart Health Service at 170 Darlinghurst Road, is a world-renowned teaching hospital and facility for cutting-edge research and one of Australia’s most famous medical establishments.

Green Park

Neighbouring St Vincent’s is Green Park, named for Alderman James Green, who represented the area between 1869 and 1883. In the 1860s, the park’s site was set to become home to ‘accommodation for aged and infirm females’, but when this plan didn’t come to fruition, the land was given over for a public recreation ground in 1875. The bandstand, which was converted into a café in the 1990s, was built in 1925 and hosted many popular public concerts in the interwar years. Today the park is also home to the Gay and Lesbian Holocaust Memorial and the Victor Chang Memorial.

Darlinghurst Fire Station

In the early 20th century, another prominent Darlinghurst Road landmark was built at the corner of Victoria Street – the Darlinghurst Fire Station. Opened in 1912, the Walter Liberty Vernon-designed station was designed with the comfort of the firefighters top of mind, with ‘seven separate residences for the married men’ and ‘a suite of rooms for the single men.’ At the time of its construction, the brick and stone station was lauded as ‘one of the finest fire stations’ and an ‘ornament to the district’, and in a testament to its designers and builders, it is still in operation today.

Bohemian wonderland

In 1916 the Kings Cross Theatre opened across the road from the fire station. Described as ‘particularly lavish’, the cinema sat more than 2000 patrons. The opening of the theatre saw cafes and restaurants spring up around it, such as the Café Eldorado, the Paris Café, the Kookaburra Café (famous for its cakes), and the Psaltis Brothers Café (a fish and oyster bar), all on Darlinghurst Road. The area developed a cosmopolitan reputation as a destination for night-time entertainment. The proliferation of cafes on Darlinghurst Road gave rise to an increasingly bohemian atmosphere, and artists and writers flocked to the area. Archibald Prize-winning painter William Dobell lived on the corner of Darlinghurst Road and Roslyn Street in the early 1940s, and writer Dame Mary Gilmore lived at 99 Darlinghurst Road from 1933 until 1962. This is the Darlinghurst Road so memorably captured in Max Dupain’s iconic image Rush Hour in King’s Cross, which depicts the frenetic energy of trams and cars at the intersection of Darlinghurst Road and William Street in 1938.

The Sydney Jewish Museum

In 1923, the Maccabean Hall was opened at 148 Darlinghurst Road. Also known as the NSW Jewish War Memorial Hall, it was built to commemorate the 800 Jewish soldiers from NSW who enlisted during World War I, 100 of whom were killed. The hall became a hub for Jewish life in Sydney before being selected as the site for the Sydney Jewish Museum. Opened in 1992 by the generation of Holocaust survivors who made new lives in Sydney, the Museum showcases the central beliefs of Judaism, and stories of the Holocaust and Jewish life in Australia since the First Fleet.

The Woolworths Building

In 1939, the Woolworths Building was erected at 50 – 52 Darlinghurst Road. While Woollies occupied the ground floor until 2001, the other floors of this gorgeous Art Deco building have served many important purposes. During the Second World War, the upstairs Balcony Restaurant was used as a canteen for servicemen. In 1949, the ABC leased the top three floors and turned them into studios, broadcasting the ABC radio news, launching ABC Television in 1956 and hosting the rehearsals of the Sydney Symphony Orchestra until 1964. The ABC moved out in 1985, and the City of Sydney purchased the building in 2002. Today, it’s the Kings Cross Neighbourhood Service Centre.


During the Second World War, bars, strip clubs and late-night venues sprang up along Darlinghurst Road to entertain servicemen stationed at nearby Garden Island. Establishments such as the Hasty Tasty, one of Sydney’s first all-night eateries, drew in prostitutes, servicemen and night dwellers from its opening in 1940 and into the 1960s and the Vietnam War era. Perhaps capitalising on the Hasty Tasty’s clientele, the notorious Abe Saffron opened The Pink Pussycat strip club upstairs in 1958. When this stretch of shops was replaced by high-rise, this spot became home to the famous Coca-Cola sign, erected in 1974. The largest billboard in the Southern Hemisphere, it has become an icon of Kings Cross and Sydney as a whole.

Darlinghurst Road today

Today, Darlinghurst Road’s seedier days are behind it. It now represents the best of the melting pot that is Darlinghurst and Kings Cross – a vibrant, living thoroughfare lined with excellent restaurants, atmospheric bars and pubs, soothing green spaces, world-class community amenities, popular tourist accommodation, stylish and chic homes, and important cultural landmarks. You can see Darlinghurst Road in party mode on Sunday 19 February 2023, when it will be closed to car traffic for a street festival as part of the City of Sydney’s Sydney Streets program.

If you’re thinking about buying, selling or investing on Darlinghurst Road or the surrounding Darlinghurst and Kings Cross neighbourhood, get in touch today.

Photo credit: Wikipedia

Article by Jason Boon

In a real estate market that is the focus of Australian, and indeed worldwide attention, Jason Boon's results in the Sydney scene make him a highly significant figure within the industry. A long-term specialist in the Potts Point and inner eastern suburbs area, he is uniquely placed to leverage his skills and local knowledge as the area undergoes significant change and diversification. Jason ha…