Richmond School is in line for a £19m investment that will see all secondary age children taught on one site in the town.
North Yorkshire County Council has earmarked the school to receive up to £19.2m from the latter stage of the Government's Building Schools for Futures programme.
At present, the school is on two sites, a mile apart. The lower school caters for 250 year seven pupils in premises near the river, while 1,400 students in years eight to 13 are taught at the main upper school, in Darlington Road.
Education officials say teachers are wasting their time travelling between the schools, which has a major impact on efforts to raise standards.
Detailed plans are yet to be drawn up, but it is believed the money would pay for a combination of new classrooms, alterations to existing buildings and demolition of outdated facilities at the Darlington Road site.
The lower school building would then be sold.
Cynthia Welbourn, director of education, said there were a number of problems with the current arrangement.
"The longer than normal teaching periods, and the movement time built into the timetable for staff to commute between the two sites, in a hire minibus or by private car, restrict curriculum development and this results in a significant loss of teaching time each week," she said.
"This is believed to be a significant restriction on aspirations to raise standards.
"It is a very large school and investment would benefit a large number of pupils and address most of the school's issues.
"To address split-site and other modernisation issues at Richmond School would be impossible through normal procedures."
Miss Welbourn described the offer of funding from the Government as a unique opportunity for the school.
She said recent development work at Richmond's St Francis Xavier School should not mean that Richmond School should miss out on the money.
"It would be wrong to deny the opportunity of a major investment to Richmond School simply because a neighbouring school was fortunate also to previously achieve funding via a different avenue."
The council's executive will discuss putting Richmond School forward for the grant at its meeting on Monday.
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