Luke Dirkzwager, of Prista Apartments in Christchurch, was granted permission in 2010 to demolish the buildings at 372-392 Princes St and 11 Stafford St.
That came only after his consent application in 2008 triggered two years of hearings, petitions, public meetings and heated opposition, before the council's hearings committee decided to grant consent.
However, the fate of the buildings has hung in the balance ever since, after the New Zealand Historic Places Trust appealed to the Environment Court and other parties joined in.
An Environment Court hearing had been scheduled for the middle of last year, but was delayed until later in the year, and then again to an unconfirmed date later this year.
Environment Court staff in Christchurch were not available yesterday, but Mr Dirkzwager told the Otago Daily Times his legal team and designers were still talking to NZHPT representatives.
Changes were still being discussed, but he hoped to reach agreement by the end of the month that would avoid the need for a court hearing.
Mr Dirkzwager's original plans would have replaced the old buildings with a development including 15 apartments, retail space and new facades referencing the originals.
However, the NZHPT has since pushed for the heritage value of the four facades - which have district plan protection - to be retained as part of the development.
NZHPT Otago-Southland area manager Jonathan Howard, in an emailed response to questions, said the trust still hoped for ''the best possible protection and retention of the building's facades as can be reasonably achieved''.
Dunedin heritage building advocate Peter Entwisle - one of the parties to join the appeal - has previously indicated an agreement protecting the facades was close, although ''far from ideal from a heritage point of view''.
Yesterday, he said the proposed compromise ''doesn't seem like an ideal solution . . . but a compromise is a compromise''.
''Certainly the developer has conceded quite a bit . . . so they probably don't see it as perfect, either,'' he said.
