Discover Darlinghurst, known as Darlo to the locals – once home to Sydney’s criminal underbelly and now an inner-city haven of Victorian architecture and East Sydney chic.

Darlinghurst’s colourful history

The Gadigal People are the traditional custodians of the Darlinghurst area.

The area was known by the European settlers as Woolloomooloo Hill, or Eastern Hill, until the late 1820s, when Governor Ralph Darling named it Darlinghurst in honour of his wife.

In the 1830s, the Governor chose the Darlinghurst ridge as the site for a row of new homes for the colonial elite. The houses were intended to be the symbol of a new high-status area.

Meanwhile, by the mid-1880s the area south of William Street was completely developed with terraces housing the workers from the wharves of Woolloomooloo Bay and their families, many of which would come to be considered slums.

The ridge was the preserve of the wealthy and the valley was where the workers lived, and so the diversity within Darlinghurst began.

During the 1920s the area picked up a new nickname: Razorhurst. Since the end of World War I, there had been an upsurge in organised crime in Darlinghurst, with criminal gangs heavily involved in the sex industry, sly grogging, illegal gambling, and the drug trade. Darlinghurst’s most famous madam, Tilly Devine, headed up one of the gangs, and Kate Leigh, ‘the Queen of Surry Hills’, the other. The gangs’ weapon of choice was the cut throat razor. The razor gang wars, as they were known, came to an end in the early 1930s but not before several bloody battles and a number of deaths.

After World War II, migrants were attracted to Darlinghurst by affordable housing and its proximity to the city and the wharves, and from the 1960s they were joined by artists, students and young professionals.

Since the 1980s Darlinghurst has also gradually shaken its reputation as a red light district. The terraces were ripe for restoration, and gentrification began, leading ultimately to the highly sought-after Darlinghurst of today.

Property market update: Darlinghurst real estate

Darlinghurst’s proximity to the city and its buzzy dining and cultural scenes are a drawcard for young professionals, as well as downsizers. 42% of residents are professionals, 78% of them are single and their median age is 35.

The majority (77%) of Darlinghurst’s residential properties are apartments, with renowned buildings including Republic on the site of the old Sargent’s pie factory, and the Harry Seidler-designed Horizon. Charming Victorian terraces or semis comprise 21% of Darlinghurst’s homes, and there are only 25 free-standing houses in the suburb.

As of September 2020, Darlinghurst’s median house price is $1,835,000, and $1,112,500 for units, according to Over the last five years, Darlinghurst has seen a compound growth rate of 5.4% for houses and 7.6% for units. The last twelve months have been especially strong for unit prices, with the median price increasing steadily month-on-month to reach the current median of $1,112,500.

With 62% of Darlinghurst residents renters, it’s worth the attention of property investors. Houses in Darlinghurst rent out for $850 per week, with an annual rental yield of 2.4%, and units rent for $550 per week with a rental yield of 2.6%.

5 reasons the locals love Darlinghurst

1. Location

Once home to Sydney’s famed razor gangs, today Darlinghurst is a gorgeously eclectic suburb offering residents the ultimate east Sydney inner-city lifestyle. Nestled amongst Woolloomooloo, Kings Cross and Rushcutters Bay to the north, Paddington to the east, Surry Hills to the south and Hyde Park to the west, it’s a mere stone’s throw from the CBD.

Streets filled with lovingly restored Victorian terraces are dotted with some of Sydney’s best bars, restaurants, cafes, galleries, and shops. Darlinghurst is bordered by William Street and Kings Cross Road to the north; Boundary Street to the south east; Oxford Street, Goulburn Street, Crown Street, Riley Street, Campbell Street and Flinders Street to the south west, and College Street to the west.

Darlinghurst has long been home to both the wealthy and the working class, the criminal and the respectable, and families and singles, and its diversity is part of its charm. So is its position, within walking distance of the CBD and Kings Cross station.

2. Lifestyle

Darlinghurst has lifestyle appeal in spades. There are plenty of petite commercial art galleries, and designer boutiques selling everything from furniture to books to vintage clothing. When it comes time to grab a bite to eat or something to drink, Darlinghurst offers seemingly endless choice. Shady Pines and Love, Tilly Devine are both pioneers of the Sydney small bar movement and still going strong. Lankan Filling Station won Time Out’s Restaurant of the Year in 2019 for its Sri Lankan fare, and Lucio Pizzeria has been serving up authentic Neapolitan pizza to Darlo locals since 2008. For live music, there’s Oxford Art Factory, and from the Green Park Hotel to the East Village Hotel, there’s no shortage of pubs.

3. Culture

Darlinghurst is home to such cultural treasures as the Australian Museum, opened in 1857 and Australia’s first public museum. The Sydney Jewish Museum is also found in Darlinghurst. For theatre buffs, The Darlinghurst Theatre Company operates from the Eternity Playhouse, housed in a restored 129-year-old building.

Darlinghurst has a proud LGBTQI+ heritage and the Sydney Gay and Lesbian Mardi Gras, one of Sydney’s biggest festivals, is centred on Darlinghurst. The first Mardi Gras took place in 1978, when a group of gay liberation activists staged a demonstration parade along Oxford Street to Hyde Park and back up William Street to Kings Cross. A riot ensued when they clashed with police. Today Oxford Street is one of the places where Sydney’s LGBTQI+ community is at its most visible and proud. The Stonewall, Arq, the Colombian Hotel and the Oxford Hotel are amongst Darlinghurst’s best-known LGBTQI+ institutions.

4. Schools

Darlinghurst Primary School is situated on Womerah Avenue. Darlinghurst is also home to two of Sydney’s oldest private schools – Sydney Grammar School on College Street and SCEGGS Darlinghurst on Forbes Street. The National Art School has been in operation at the historic Darlinghurst Gaol site since 1922.

5. Hospitals

Established in 1857 as a free hospital for Sydney’s poor, today St Vincent’s Hospital and St Vincent’s Private Hospital are leading medical, surgical and research facilities offering a comprehensive range of services and treatments.

If you’re interested in buying or selling in Darlinghurst contact my team today.

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…