If the walls of our historic buildings could talk, they would tell some fascinating stories from the past.
So what's in store for the next chapter of these sites?
Here's what the future might hold for some of our most notable old buildings.
Bowral Courthouse owner Deborah Pollock said she has had "a lot of offers to purchase [the building] for restaurants, bars and offices".
"I would love to see it as a gallery with opportunities for a wine bar and cafe so it becomes a destination," she said.
"There's a couple of very interested parties. It's currently being used as a small marketing office."
There's been suggestions by members of the public that the courthouse would have been a good location for the Southern Highlands Regional Art Gallery.
Wingecarribee Shire Councillor Larry Whipper, who was involved in scouting the locations for the gallery, said he inspected Bowral Courthouse "some time ago, prior to this current proposal".
"It is not really suitable for a number of reasons. It is a heritage building and any internal works to accommodate artworks of the quality exhibited in a regional gallery would be prohibitive. The building is small and not really fit for purpose," Cr Whipper said.
"Council did make an approach to the government when the courthouse was decommissioned with a request to purchase at a reasonable price, but the government went to open market."
Councillor Whipper said Retford Park was the right location for the project.
"In my opinion, and the opinion of many others, offers a unique opportunity with an iconic setting," he said.
Berrima Correctional Centre
Berrima Correctional Centre's future is uncertain.
In September it was announced the facility would close, less than three years after it opened and a year after it was recommissioned as a women's prison.
A Corrective Services NSW spokeswoman said there would be a community consultation process to determine the future of the facility.
"We will continue to consult with the Wingecarribee Shire Council and stakeholders on the future use of Berrima Correctional Centre and will keep the community informed as this progresses," the spokeswoman said.
"We are also working with experts from the Department of Planning, Industry and Environment to undertake consultation and ensure the community and businesses can have their say about the future of this facility."
Likewise the future of the Mittagong Maltings is uncertain.
A Medich Corporation spokesperson said plans for the secured site could be finalised in the next few months.
The spokesperson has previously said there are no plans to turn the property into a drinking establishment.