Conservationists have raised strong objections to a proposed development of 158 flats set in blocks of up to 10 storeys high.
Developers want to demolish the former Grays of Chatham Used Car Centre to make way for the high-rise apartments in the High Street.
The scheme submitted by Option Two Development has incensed members of the City of Rochester Society who have branded it, "dull, outdated and not in-keeping with its historic surroundings".
The group's chairman Rob Flood has written to the council's planning department, saying there were "serious concerns" about the "almost unbelievably inept and dull architecture".
He also slammed "poor living conditions, tiny windows creating dark and unpleasant flats".
Last week, the firm submitted fresh plans, upping the number of flats by six.
The proposals would involve demolishing the pre-existing buildings on the site in order to build four blocks between three and 10 storeys.
Documents presented to the planning department say there had been concerns raised by officers and councillors that one of the blocks in a previous design was too high, and the block facing the High Street needed redesigning.
The developers want to provide 115 one-bedroom flats and 43 with two bedrooms.
Under the plans, there would be 45 parking spaces. It also wants to see the development have a connection with the existing river walk.
Three of the blocks would have commercial space in the ground floors, with the developers suggesting possible uses include shops, a gym, and a cafe.
The development also includes a new river walk, a "plaza" and ampitheatre which could be used for performances and live events.
Another letter of objection has been sent from the chairman of the neighbouring Hospital of Sir John Hawkins – an almshouse for naval pensioners.
Neil Wood says the demolition work alone would create "a year's worth of heavy traffic for which the High Street is ill-suited".
The council is due to make a decision by Wednesday, September 14.
Grays, a family-run business, has been trading in the town for more than 80 years selling bicycles, motorbikes, cars and vans.
Over the decades it expanded into Maidstone, Sittingbourne and Gillingham.