An application, submitted by Alex Baillie, seeks permission to build on the empty plot of land off High Street.
The council’s planning board - whose members will mull over the scheme on Tuesday - previously awarded consent in 2015 and 2018, but neither came to fruition.
However, approval has been earmarked for two two-bed bungalows, nine two-bed houses, 21 three-bed properties and eight four-bed homes - despite traffic issues, loss of privacy and a loss of habitat being submitted to Barnsley Council.
Dave North, chairman of Shafton Parish Council, said: “The site has had a history of approved-but-failed planning applications, but concerns remain over its suitability and it isn’t hard to see why.
“Adding 40 homes’ worth of cars onto an already busy main road is the main reason why people are worried.”