Local Street History: Cleveland Street

October 20th, 2023 - by Brad Gillespie

Cleveland Street is one of Sydney's busiest thoroughfares.

Running from Moore Park, at the intersection of Lang Road and Anzac Parade, through to Victoria Park on City Road. It’s a 2.8-kilometre stretch of road that connects the eastern suburbs with the inner west, spanning Chippendale, Darlington, Redfern and Surry Hills.

Before the street: a garden and house

The area around Cleveland Street has a long association with the name Cleveland.

In 1809, Governor Macquarie granted land in the Surry Hills and Redfern area to Charles Smith. He established Cleveland Gardens, which operated as a market garden or nursery.

Around 1820, Daniel Cooper, a convict turned merchant, purchased around 12 acres from Smith. He built Cleveland House, a colonial mansion believed to have been designed by Francis Greenway. It still stands today at 146-164 Chalmers Street, Surry Hills and is listed on the NSW State Heritage Register as “a rare surviving gentleman's residence of the 1820s an example of a good quality residence of the time.”

The name: Cleaveland or Cleveland?

There has been debate for many decades over who the name Cleveland comes from. One school of thought is that Cleveland Gardens, and Cleveland House could have been named after the English Lord Cleveland (1766-1842) who was appointed the Duke of Cleveland.

The other candidate was Captain Cleaveland, an officer of the 73rd regiment. Other sources even attribute Captain Cleveland as having built a house on the land.

An article in a 1930 edition Royal Australian Historical Society journal stated: “Tradition says that Cleveland House was built by or for Captain Cleaveland, of the 73rd Regiment, which arrived in Port Jackson on December 28, 1809. The regiment remained in Sydney for four years, and it is assumed that the house was built for him as an official residence.”

However, the journal was also sceptical: “It is difficult to think that such a mansion was built by a Captain in a marching regiment,” it concludes.

Neither the State Heritage Register, nor early maps make any mention of Major Cleaveland, attributing Cleveland House to Daniel Cooper.

But what about the street?

Both Cleveland Gardens and Cleveland House pre-date Cleveland Street by many years.

According to the City of Sydney, maps prior to 1840 mark Cleveland Street as a surveyed 'Government Rd'. A map from 1835 shows an unnamed Cleveland Street sitting just north of Cleveland House, and marked simply as “New St. proclaimed by Act of Council”.

A slightly later map from 1842 of allotments for sale on the Redfern Estate shows Cleveland Street with the note “named by Sir T M Mitchell”. Cleveland House and its landholdings extend south, stretching more than a whole block. Sir Mitchell was Sir Thomas Livingstone Mitchell (1792-1855), surveyor-general in the Colony of Sydney.

The street quickly became pivotal and in the early 1860s, residents along Cleveland Street signed a petition “for repair of this important public thoroughfare, which is now in a deplorable state, and for continuance of Cleveland Street to the New Town Road, as projected, as soon as practicable.”

Shaking a bad reputation

Cleveland Street forms part of the suburb border of Surry Hills.

While the Surry Hills we know and love today is built around a stylish cultural and village centre, it wasn’t always this way.

From the late 1800s to at least the 1940s, Surry Hills and its neighbouring suburbs along Cleveland Street - such as Darlington, Chippendale and Redfern - were notorious for gangs, crime, and slums. Some of these slums were documented by photographer Max Dupain.

Ruth Park's 1948 novel The Harp in the South reflected the realities of life in 1940s Surry Hills and the stigma attached with living in the area:

“A Surry Hills girl finds it difficult to obtain a position in the city. She may be educated, she may be more highly moral than similar young ladies in more prosperous suburbs, but her address is against her. Most Sydney people persist, somewhat biasedly, in thinking of Surry Hills in terms of brothels, razor gangs, tenements and fried fish shops.”

A Royal visit to a busy road

On 3 February 1954, Cleveland Street became part of the 10-mile-long royal procession of Her Majesty Queen Elizabeth and H.R.H. Duke of Edinburgh. A photo from the day shows the street teaming with people.

Also visible in the photo are the overhead cables for the electric trams that ran the length of Cleveland Street until 1958. While it’s quieter these days, Cleveland Street has always played an integral role in our city’s transport network. It was originally declared a Main Road in the 1920s and, in 1964, formed part of Sydney's first Ring Road system as “Ring Road 1”.

It became “State Route 11” in 1974, before being renamed “Metroad 4” in 1992. After its completion in 2000, this metroad was re-routed to City West Link, leaving Cleveland Street a little quieter.

Landmarks on Cleveland Street

Residential, commercial, entertainment, and retail: Cleveland Street has it all. The streetscape also reflects the architectural eras common in its surrounding suburbs - from modern apartment buildings to converted warehouses, Victorian terrace houses, cafes and art deco pubs. Some landmarks include:

The Seymour Centre

Part of Sydney University on the corner of City Road and Cleveland Street, The Seymour Centre opened in 1975 and was designed by Allen Jack+Cottier.

Prince Alfred Park

According to Sydney Barani, this area was an Aboriginal campsite until the mid-19th century, when the railway was established. Dedicated in 1850 as a park called Cleveland Paddocks, from 1869 it was used as the showground for the Agricultural Society, and hosted the first Australian Exhibition in 1870.

The park’s layout was designed by Benjamin Backhouse, a celebrated Victorian architect. The informal row of Moreton Bay fig trees along the boundaries reflects the layout from the original 1870 plan.

These days it has an excellent children’s playground, tennis courts, recently revamped pool, and a rainbow pathway and equality green.

Inner Sydney High School

A school has existed on or near this site since 1856, when a “model school” was established in Cleveland Paddocks. The iconic sandstone Gothic buildings were constructed in 1867-68, and it has since had various incarnations, from a primary school to an intermediate school, boys’ high school and English Language Centre. Today, the new Inner Sydney High School is housed in a high rise behind the original stone buildings. It accommodates 1,200 students.

Inner Sydney High School is popular with locals, but it is not the only school on Cleveland Street. At the Moore Park end are coveted top-performing selective high schools, Sydney Boys and Sydney Girls High.

Properties on Cleveland Street

We have recently sold 4/187 Cleveland Street, Redfern. A fabulous two-bedroom unit, with one and a half bathrooms across 83 sqm, it is right opposite Prince Alfred Park, offering low maintenance city convenience in the popular and pet-friendly 'Strawberry Apartments'.

If you’re interested in making Cleveland Street your home, contact us today.