Derelict buildings in the centre of Cupar could be bulldozed to make way for new housing and retail.
Demoltion of factories behind Crossgate and Bonnygate and redevelopment of the site would enhance the town centre, claim those promoting the scheme.
Fife Council wants to use £450,000 of Scottish Government town centre funding to kick-start the work.
The site includes derelict buildings behind Fisher and Donaldson bakery and the Bonnygate gap site where a dangerous building was demolished 10 years ago.
Kingdom Initiatives, a subsidiary of Kingdom Housing Association, has applied for permission from Fife Council to demolish several structures in what is referred to as the Inner Court area.
A planning application is to be submitted for construction of housing and a retail unit, with a proposal to also enhance pedestrian links to Bonnygate, Crossgate and Kirk Wynd.
Kingdom Initiatives’ agent Sinclair Watt Architects told the council the significant area of derelict and vacant land “undermines the prosperity of the town”.
It said: “The re-development proposals for the Inner Court area of Cupar will make an important contribution to the regeneration of the town centre by improving a visually unattractive and derelict site on an important thoroughfare between the main car park to Cupar’s town centre.
“Approval for the demolition of the derelict buildings on the site in advance of the planning application for the main redevelopment will allow removal of the dangerous buildings to facilitate important survey and investigation work which, in turn, will result in more detailed and accurate redevelopment proposals.”
The buildings to be demolished, including a former chocolate factory, were said to be in a ruinous state.
Intrusive site investigations are to be conducted and detailed survey work.
Cupar Development Trust revealed a blueprint for the site four years ago, involving creation of 34 homes and nine business units.
It developed the vision with Fife Council, Kingdom Housing Association and Fisher and Donaldson.