Dennis Friend, owner of Trinco House, Penhow, Newport, Gwent, had challenged the notices which accused him of breaching planning control and required removal of substantial development works.
The first notice - Notice A - issued by Newport CBC alleged an unauthorised change of use to a dwelling house of a one-storey building formerly used for pleasure purposes.
The second - Notice B - alleged the erection of another one-storey building and lamp standards along a driveway without planning consent. And the third - Notice C - concerned construction of a driveway across what had been agricultural land.
Mr Justice Turner told London's high court: 'The works to which the council took exception were its conversion into what it claimed was a self-contained unit of accommodation' occupied by Mr Friend's son.
The judge said it was the validity of Notice A which had been 'most strenuously contested' before him. After a public inquiry, a planning inspector had upheld Notice A saying the change of use was 'harmful to the residential amenity' of the main house.
Mr Friend's lawyers argued the inspector had wrongly treated the building 'as if it were a new building, rather than the conversion of an existing one'. He had also failed to give adequate reasons for his ruling that the change of use conflicted with the local development plan.
The inspector, they claimed, had also wrongly concentrated on the issue of precedent, saying the council would 'encounter difficulty in resisting other unjustified development in the countryside' if the change of use were accepted.
Dismissing Mr Friend's appeal, Mr Justice Turner concluded: 'The essence of the inspector's findings were matters of fact and sensible interpretation of the structure plan.'
The inspector had been entitled to hold that what Mr Friend had done was 'tantamount to the provision of a new dwelling in the countryside' and that that was 'contrary to the spirit' of the development plan.
'In my judgement, the reasons why he came to the conclusion which he did could scarcely have been expressed more clearly, albeit, had he expressed himself more forcefully, the applicant might have felt some inhibition from pursuing this hopeless ground of challenge,' the judge said.
Turning to the precedent issue, the judge added: 'It was inevitable that he (the inspector) should have found that to permit such development would have rendered it hard for the council to have resisted any similar appeals which might be made in the future.
'Here was an unpermitted development in the countryside which had proceeded largely by a circuitous and tactically devised route as if by such means the essentials of the declared policy could thus be overcome.
'It was, if not sporadic development in the countryside, the next thing to it. As such I entertain no doubt but that the applicant has failed to make good his point that what was happening was the use of a pre-existing building for a different purpose.
'That was a barely disguised and legally disingenuous submission which was at odds with the true position.'
Turning to Notices B and C, the judge said: 'The findings of the inspector clearly envisaged that, in the period since 1991, there had been a change or changes of use of different parts of the property.
'Thus, the hardstanding, the tennis court, the drive, the curtilage and the gardener's shed to identify but some of those changes.
'It is, in my judgement, clear beyond argument that the inspector regarded what had happened as one scheme which might properly be described as the 'sub-urbanisation' of the property.'
Mr Friend's appeal was dismissed in respect of all three enforcement notices.