David Daly of Albany Homes paid fellow construction tycoon Gerry Gannon €25m for the plot in June 2006, equating to an eye-watering €133m an acre.
The transaction -- which set a land price record here -- took place in the middle of a property buying frenzy in Ballsbridge at the height of the boom.
Since acquiring Franklin House, Mr Daly has been beset by planning objections from local residents and the effects of the economic downturn.
October Management has applied to Dublin City Council to demolish the four-storey building at 140-142 Pembroke Road and replace it with a new three to five storey block.
The plans provide for solar panels at roof level and terraces on the third and fourth floors.
The council gave permission for the demolition of Franklin House four years ago, only for the decision to be overturned by An Bord Pleanala.
The previous plans provided for a block of up to eight storeys but led to a slew of objections, most notably from business tycoon Dermot Desmond.
In 2005, developer Sean Dunne splurged €260m on the Jurys Ballsbridge hotel site, working out at €53.7m per acre, while Ray Grehan of Glenkerrin Homes splashed out €171.5m (€84m an acre) on the former UCD veterinary college building on nearby Shelbourne Road.
Bernard McNamara later paid the Jurys Doyle Group €288m for the Burlington Hotel in Dublin 4. He followed it up with the purchase of the Allianz building next door, paying €100m for the 1.5-acre plot.
Objecting to Mr Daly's 2008 plans for Franklin House, Mr Desmond wrote: "The proposed development is... premature pending the provision of an action area plan/ local area plan for the Ballsbridge area. In those circumstances, I would submit that it would be appropriate to refuse this application as being contrary to the provisions of the development plan."