David Stevens, of 232 Lanehouse Rocks Road, Weymouth, Dorset had hoped to win the go-ahead to mount a full High Court challenge,
He was contesting Weymouth and Portland Borough Council's refusal of planning permission for the development planned by his company, Foundation Homes (South West) Ltd, for a site next to Augusta Road, The Grove, Portland.
He claimed that the proposal was rejected by the Council's Planning Committee on a tight 6-4 vote.
However, he argued that two councillors who voted against him should have stood down from the committee.
He claimed that the vote would then have been tied, with the casting vote falling to the Vice Chair, who had spoken strongly in favour of the development during the meeting.
He asked Mr Justice Mitting to grant him permission to bring a full High Court challenge to the Council's decision at a later hearing.
However, the judge today rejected his case, ending his hopes of forcing the Council to reconsider the decision.
The judge said that "on no view" could the facts alleged by Mr Stevens give rise to a suspicion that a councillor had an interest, let alone a prejudicial interest, in the matter which was the subject of the planning committee's deliberations.
"Accordingly any challenge to the decision of the committee on that ground must fail," the judge said.
Mr Stevens will now have to make a fresh application for planning permission if he hopes to revive his development plans.
The judge today also ordered him to pay £675 towards the legal costs of today's hearing.