Shanly Homes want to knock down the vacant building and build eight new two-bedroom flats.
It is the latest in a long line of applications submitted by the developer. Previous planning bids have been repeatedly rejected by the Maidenhead Development Control Panel.
In February it was refused permission to build nine flats at the site amid concerns over the increased footprint of a new apartment block.
Fears a supermarket could move into the site were also raised after it was revealed Shanly Homes was in 'advanced talks' with Sainsbury's.
Cllr Geoff Hill (Con, Oldfield), cabinet member for highways and transport, is urging councillors to approve the latest application to avoid any chance of the supermarket giant moving in.
"This new application I am very pleased with because it is significantly smaller," said the Ray Mead Road house-holder.
"It is what the overwhelming amount of people want here on the Riverside."
A decision is due by May 14.
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The victim of an assault in Cippenham was flown to hospital by air ambulance this afternoon.
A rapid response vehicle, an ambulance officer, an air ambulance and an ambulance crew were all called to an address in Earls Lane at 2.10pm.