The council is taking legal action following the expiry of a deadline to demolish the old Saint John's orphanage.
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In early November, councillors set a January 31 deadline for owner, John Ferrara to bulldoze the remains of the fire-damaged former catholic orphanage in Mundy Street.
This was based on public safety grounds, given its state and presence of asbestos.
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But councillors heard at their meeting on Tuesday that the remains of the 1912 building were still standing.
Environment and planning director Scott Martin said his department was looking at legal options this week.
"We'll keep councillors in the loop with briefings but this could be the start of a long road," he said.
However a spokesman subsequently told The Post the council would seek a NSW Land and Environment Court order to demolish and remediate the main building and recover costs.
"The owner has also not complied with previous directions regarding other buildings on site, for which legal proceedings have already begun," the spokesman said.
Mr Ferrara said it was not an easy job and he'd been trying since before Christmas to enlist a demolition firm.
"I am doing it. They (previously) gave me one month to do it, which made no sense, then did a 180 and said four months," he said.
"It will probably take a month to demolish but it's just a matter of getting someone."
Mr Ferrara estimated the cost at up to $500,000, which he said he didn't have freely available.
The previous council called for the demolition last July. At the time, the then deputy mayor Peter Walker argued the public safety risk far outweighed any heritage considerations on the EC Manfred designed structure.
When nothing had happened at the site, in November they set the January 31 demolition deadline. If not met, the council would seek a NSW Land and Environment Court order to demolish the building itself and recover costs from the owner.
Mr Ferrara had previously been issued demolish works and public safety orders. In September/October he was handed a $3000 Penalty Infringement Notice for non-compliance with the public safety order, which required him to secure loose iron, fencing and the outer buildings. This has since been completed.
But the main structure remains the concern.
Mr Martin told The Post there were several legal options, including Land and Environment Court action which required "a higher burden of proof" and greater preparation than the Local Court.
Mr Ferrara had contacted planners around Christmas for an extension but as the new council was not in place, no decision could be made.
Staff had earlier conceded the difficulty of securing labour during the COVID-19 pandemic.
On Thursday, Mr Ferrara said he had bulldozed the former caretakers cottage at the rear and a former gym. The remains are visible at the site.
These were among three structures that had to be fully demolished by November 12. Mr Ferrara said he would shortly commence on the other at the orphanage's rear.
The November 2 council decision authorised staff to commence proceedings in the Local Court if the November 12 timeframe wasn't met. This has been enacted.
Meantime, Mr Martin said there was conjecture around whether an earlier development application for a residential development on the site was still active.
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This was proposed in about 2013/14 but Mr Ferrara has since abandoned this and said he wanted to build a four to five-storey apartment block. He claimed last year the earlier DA was still active.
But Mr Martin said as that DA was dependent on the orphanage's continued presence.
"There were also a lot of conditions around heritage conservation. We haven't gone completely down that road yet because our feeling is that, without the orphanage there, it changes things," he said.
"Once we've dealt with the issue at hand (demolition) we can look at whether the consent is valid, regardless of whether it's been activated or not."
However he believed the new apartment concept was "completely new space."
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