Forty new homes could be introduced in the grounds of Leigh Infirmary - under plans lodged with Wigan Council.
Late 19th century property The Limes, which used to house hospital doctors, would be pulled down under proposals drawn up by Wigan-based developer David Evans.
Critics say the property, constructed by cotton magnate John Heyes, should be preserved, like nearby grade II listed Hollybank, the former missionary convent built for his brother James.
But the building itself, sandwiched in grounds between Orchard Lane and the infirmary car park, has been vacant for around seven years.
An outline scheme, drafted by Mr Evans, shows the homes arranged around a horseshoe-shaped road, with an additional entrance envisaged off Orchard Lane.
Planning agent Richard Moffatt said: “The scheme vision is to provide a high-quality residential scheme whilst maintaining the unique landscape character and green infrastructure throughout and adjacent to the site.”
Forty-one individual or groups of trees are covered by a woodland protection order and a survey of how they would be safeguarded would have to be submitted with any full planning application.
But the developer has said efforts will be made to retain mature trees and minimise the impact on Hollybank, which was first listed by English Heritage in the mid-90s.
Mr Moffatt added: “We believe that the planning history of the Hollybank site demonstrates that it is possible to develop in the vicinity of the listed building without affecting its character, appearance and setting.
“The proposed development on the application site would be sited further from the listed buildings than the most recent development on the Hollybank site and be separated by a belt of existing trees, which would be maintained.”
Supporters of the bid are relying upon the fact that the Leigh area is the focus of the borough’s primary housebuilding plans.
Photographer Mike Turner, who took a series of pictures of The Limes three years ago, said on his website that it would be “another sad loss to Leigh’s heritage” if The Limes was to be lost.