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Luke Dirkzwager, of Prista Apartments, has been granted Environment Court approval to demolish the buildings at 372-392 Princes St and 11 Stafford St, making way for a mixed-use retail and apartment development.
However, three of the buildings' four facades have been spared the wrecking ball, and would instead form a section of the new development, as part of a compromise with heritage advocates.
That would mean the retention of the facades at 380, 386 and 392 Princes St, while the buildings behind them - dating back to between the 1860s and 1913 - would be demolished.
The largest building, at 372-378 Princes St, would be removed with its facade, despite dating back to 1879.
Details of the deal were contained in an Environment Court consent order agreed to by all parties, made public yesterday. It ends a long-running battle over the development dating back to 2008.
Mr Dirkzwager is overseas and could not be reached yesterday for comment about a start date, but the revised consent approved by the court gave him until 2021 to advance the project.
Heritage advocate Peter Entwisle, who was involved in negotiations over the project, said he had been told the development was unlikely to proceed for at least five years.
Mr Dirkzwager was now said to be busy with other projects in Christchurch, and had sought an extended consent deadline, Mr Entwisle said.
While welcoming the decision to spare three of the facades, Mr Entwisle was disappointed some of the city's original Gold Rush-era buildings would be lost.
''In terms of heritage there's a big loss ... This is the original townscape that had survived almost intact,'' he said.
However, Heritage New Zealand Otago-Southland area manager Jonathan Howard described the deal as a ''reasonable outcome'' after his organisation pushed to protect all four facades.
The loss of buildings would damage heritage values in the area, but the development would also help stimulate the area, he said.
''Clearly, there's a lot of heritage value and a lot of history in that area . . . [but] buildings need to be viable to have a future.''
The deal ended a long-running debate that began when Mr Dirkzwager first sought to demolish the buildings completely in 2008.
The outcry that followed did not stop the Dunedin City Council's hearings committee granting consent for the project in 2010, but the then-New Zealand Historic Places Trust - now Heritage New Zealand - appealed.
Mr Entwisle and another heritage advocate, Elizabeth Kerr, joined the Environment Court proceedings. The parties eventually began a protracted round of negotiations in mid-2013, in an attempt to avoid a court hearing, leading to yesterday's deal.
The court's revised consent required the facades being retained, together with the nearby category one-listed Empire Tavern, to be protected during demolition.
However, it also allowed the new buildings behind the facades to exceed the maximum height limit for the zone.
Christchurch-based architect Stewart Ross, a director of Fulton Ross Team Architects, who worked on the retention of the facades for Mr Dirkzwager, said the compromise was needed to protect heritage values while ensuring the development was viable.
It would have been ''very difficult'' to build a viable new building behind the facade of the biggest building, at 372-378 Princes St, he said.
''It's always a trade-off. If you want to get a developer in to regenerate and do a bit of work, if you make it too difficult of course they're going to walk away.''
The compromise was ''probably about the best outcome''.