Shropshire Councillor for Ludlow, Andy Boddington, who is also a member of the south Shropshire planning committee, said he is "at the end of his tether" after asking for the plans for two homes at Friars Walk to be brought to the planning committee three times.
All of the requests were refused, so Councillor Boddington complained.
Ludlow Town Council and a number of residents objected to the plans for the two semi-detached homes.
Councillor Boddington has previously labelled the plans "not safe" and "utterly crazy" as he said the construction plan cannot be delivered as it is "almost impossible to access".
Now Councillor Boddington said he is "furious" that planning officers approved the plans.
He said: "I no longer know what it takes to get a Ludlow planning application called in to be considered by the south planning committee.
"The south planning committee goes off to look at some of the most trivial of applications, café seating and a garage conversion for example.
"We go to see exemplary developments to which almost no one objects. But in Ludlow, we struggle to get applications that cause significant controversy called in to the committee."
Councillor Boddington added that the development cannot be built without "significant disruption" to residents and St Laurence's School.
He said that materials must be moved from Friars Walk across the pedestrian way during a "very restricted" time frame, with the only early morning delivery being a half an hour window between 7.30am and 8am.
After that, it will be 10am to 11am and 2pm to 2.30pm. On Saturdays, three hours are allowed between 9am and 12noon.
Councillor Boddington said the half an hour early morning slot would not work and said the idea is "cloud cuckoo land".
The development was approved by council officers, subject to conditions, on November 9.
Councillor Boddington added: "The development has been shabbily handled.
"The developer did not consult with residents or the school, or local councillors.
"Representations from democratically elected councillors have since made not one jot of difference.
"It has become a process in which the democratic contributions have become marginalised, while officers call the shots. Shropshire Council’s planning regime certainly doesn’t work for Ludlow."
Councillor Boddington said he will raise the issue with council leader Peter Nutting at a meeting this week.
Shropshire Council declined to comment.