Get involved in National Science Week with local star gazing, kaleidoscope making - and more!
Business News: Mosman teens cleaning up with mobile car wash service.

Flashback 1926: Milson’s Point homes and businesses demolished for the Sydney Harbour Bridge.

Published On: July 27, 2022

More than 3000 locals were displaced when their homes and businesses were demolished to make way for the Sydney Harbour Bridge. Image: NSW Archives.

Mosman Collective has uncovered an incredible set of images documenting the last days of Alfred St in Milsons Point before many of its homes and businesses were demolished to make way for the Sydney Harbour Bridge.


The ruthless clearing and demolition of more than 500 homes and businesses around North Sydney is one of the darker chapters in local history.

When work commenced on the Sydney Harbour Bridge in 1923, properties in its path were knocked down to build the pylons, bridge approaches, and the rail line from the new North Sydney station to Waverton.

A partially demolished building in Alfred St circa 1926. Image: NSW State Archives.

More than 3000 residents were displaced, with no offer of rehousing and little compensation from the Government.

These nostalgic remnants of the past, captured by Government photographers in 1926, show the demise of Alfred St, a once thriving business hub servicing residents with a variety of well-stocked, quality stores.

Informally composed but visually rich, the glass plate negatives provide a rare glimpse into lower north shore life before Sydney was connected by its iconic Harbour Bridge.

WINE SHOP + BUTCHER: 67 – 69 Alfred St.

The Milson’s Point wine shop and neighbouring Butcher. Image: NSW State Archives.

Wearing a waist coat and tie, the dapper man leaning against the post outside 67 Alfred St was likely Thomas Bourke, the owner of Milsons Point Wine Shop. Zoom in and you can see a neat display in the front window, with Caldwell’s wines taking pride of place. A fashionable brand in the 1920s, Caldwell’s Muscat or Port was the chosen tipple for men, with ladies often drinking socially acceptable Sweet or Dry Sherry.

Another man, wearing a striped apron, looks directly at the photographer as a woman enters the shop next door. Perhaps he is Mr W Dale, owner of the Butchery who sold prime Ox tongues, choice veal and “high-class meat”.

LAY’S MOTOR GARAGE: 87 – 91 Alfred St.

Lay’s Garage offered a full range of car sales and services. Note the petrol pump at the front. Image: NSW State Archives.

With more cars on the roads after the Sydney Harbour Bridge Act was passed in 1922, the enterprising Lay brothers thought Alfred St would be the perfect site for their motor garage, offering a full range of car sales and services.

Open day and night, the business recharged batteries, hired cars and filled petrol tanks for 2/4 pence from a “Guaranteed Shell” pump at the front of the service station.

By the end of 1926, the brothers were selling up and moving out after their land was resumed, offloading assets including a nearly new Ford 1-Tonne truck for £140.


This corner store was owned by Ernest Clayton in the 1920s. Note the neighbouring Hair Salon. Image: NSW State Archives.

Dressed in a suit and tie, a man leans on the windowsill of a grocery store, as a young girl and her dog wait at the entrance.

Perhaps the trio have accompanied the woman you can faintly see inside, who may be picking up some ingredients for dinner. The shop was owned by Ernest Clayton, who worked hard to build up his small business on the corner of Alfred and Fitzroy St.

Next door, Mr O’Connor runs the local Hairdresser and Tobacconist, offering ladies and gents cuts in a “hygienic saloon”, where children’s haircuts were a specialty.

DINDS HOTEL: 83 Alfred St.

Dinds Hotel was said to be a lower north shore institution until it was demolished in the late 1920s. Image: NSW State Archives.

William Dind was a well-known man of the arts who ran the Victoria Theatre in Pitt St (where the Strand Arcade now stands), before heading across the harbour to become a publican in the early 1900s.

His hotel soon became a popular meeting place for the “theatre set”, with its walls adorned with magnificent portraits of stage celebrities.

“Along with the actors and actresses came many legal and literary men, who “dined and wined” in that North Shore inn,” the Daily Telegraph reported in 1923.

NEWSAGENCY: 53 Alfred St.

The “paper shop” in Milsons Point also doubled as a Circulation Library. Image: NSW State Archives.

Mr A.J Gardiner ran the Milson’s Point newsagency at 53 Alfred St, selling major mastheads like the Sydney Morning Herald, the Sunday Times and the Evening News. The enterprising local businessman also ran the Milson’s Point Circulation Library along with stationery and tobacco.

In the decades before suburban libraries would become commonplace, hundreds of ‘circulating’ or subscription libraries operated in Sydney. Mr Gardiner’s service allowed residents to “rent” books for a small annual – or quarterly – fee.


Compton’s was a local Real Estate agency, helping locals find rooms, flats and houses to live in. Image: NSW State Archives.

Compton’s “Mutual Business” Agency leased houses, flats and single rooms for local workers from 1916 until it was demolished, shortly after this photograph was taken in November 1926. The small office, wedged between Mr O’Connor’s Hairdressing and a Grocery store, relocated to Glen St in 1927.

Share this story...

Get involved in National Science Week with local star gazing, kaleidoscope making - and more!
Business News: Mosman teens cleaning up with mobile car wash service.

Get The Latest News!

Don’t miss our top stories delivered FREE each Friday.

Go to Top