Back in the late 1960s, the most exciting day of the year was when my mother would take me down on the train from Gosford to Luna Park. We’d step off at Milsons Point station and wander down the steep hill to the harbour. That’s when we got our first glimpse of that smiling – and ever so creepy – face.

Luna Park had been shipped to Sydney from Glenelg in 1935, after South Australian wowsers worried it would attract riff-raff to the area and wanted it gone. When reassembled at Milsons Point, no other amusement park in the world could claim such a stunning location.

And then on a cold June night in 1979, the magic came crashing down. Six children and one adult perished in the flames of the Ghost Train fire. Luna Park would never be the same again.

The prime harbourside land on which Luna Park resides has had a long history, starting with the Gamaragal people who had lived and fished there for thousands of years. In the early 1820s, James Milson a free-settler (after whom the suburb derives its name) settled in the area and established a thriving business supplying ships with produce from his market gardens and dairy.

Milsons Point has always been an important transport hub between the city and the North Shore, whether it be via ferries, or cable trams. As early as 1815, government architect Francis Greenway proposed a bridge across the harbour. Of course, it would take 117 years until such a bridge was finally completed.

Construction of the Sydney Harbour Bridge and its approaches saw the demolition of more than 500 buildings around North Sydney and Milsons Point, leaving many people homeless and without compensation. Everything that had made Milsons Point a thriving community; the fish shops, churches, terrace homes, workers’ cottages, hotels, and even the grand colonial homes of the Milson family, were obliterated in the name of progress.

The Harbour Bridge opened in 1932, along with the railway station. With access to the area greatly improved, Milsons Point started to grow.

In 1936, the iconic North Sydney Olympic Pool opened. Situated between the bridge and Luna Park, it was designed by architects Rudder and Grout and features gorgeous art deco lines. The pool was used for record-breaking swims by everyone from Shane Gould and Michelle Ford to Lorraine Crapp.

Throughout the 1970s and into the 1980s, all but nine of the original pre-Harbour Bridge terraces were razed and Milsons Point became dominated by office buildings; home to companies ranging from Legal & General and SBS, to Yellow Pages.

From the mid-1980s, North Sydney Council changed its zoning laws, therefore requiring a greater residential component in the area. Nowadays, most of the office buildings have been transformed into luxury apartment towers.

One of the most famous Milsons Point residences is the Seidler Penthouse on the cliff top at 2A Glen Street. Designed by the late modernist architect, Harry Seidler, and his wife Penelope, the penthouse was completed in 1988, and features a double-height entry foyer, sinuous staircase, and a world-class art collection. Winner of the RAIA National Interior Design Award 1991, the penthouse is arguably Australia’s most splendid apartment.

“I’ve lived there on and off over the years; and it’s wonderful,” says Penelope Seidler. “The view, the curves, the grand space, I love it. Milsons Point has family connections, because my father lived there as a boy in one of the houses that was later demolished to build the bridge.”

North Sydney councillor Ian Mutton lives across from the Seidler Penthouse in the Pinnacle apartment building at 2 Dind Street.

“Milsons Point, in terms of its connectivity, its transport links to just about all of Sydney, is absolutely phenomenal,” Mutton says. “If you are into apartment living, as I am, then it’s an ideal position.”

Mutton is also the president of the Sydney Harbour High Line Association, a body lobbying for the old railway siding that runs from Waverton to Milsons Point to become a 3.3-kilometre, New York-style high line.

“The High Line would join the half-a-dozen isolated harbour foreshore parks, creating a mosaic of greenspace along the harbour side,” says Mutton.

“It’s crucial, because we’ve been told by the government that this whole area will see a 30 per cent increase in population over the next 20 years, and most will be housed in apartments.

“The premier has promised that the high line will be built as soon as the siding is no longer used by the railways. We could see construction start within a year.”

And as for Luna Park?

“No, I don’t think Luna Park will ever become residential,” Mutton says.

“Luna Park is one of the icons of Sydney, there with the Harbour Bridge and the Opera House. I think the community of Milsons Point and North Sydney, and the community of Sydney itself, has an expectation that Luna Park will always be there, and continue as a theme park in that sort of Tivoli 1930s tradition.”