At times of heavy rainfall water, large puddles gather in homes on Billy Wright Close, in Penn, Wolverhampton.
Accord, a housing association responsible for the maintenance of the homes, said it is looking at addressing the issue.
One councillor has called on Accord to take urgent action. The water comes off a playing field of Warstones Primary School, which is located across the road.
David Walker, aged 62, who's house on Billy Wright Close has been affected, told the Express & Star: "I only moved into the property in May but apparently the flooding has been taking place for 20 years.
"The lady next door gets it really bad. She is 80-years-old.
"Accord know about the problem, it is frustrating.
"What happens is the water comes off Warstones School, it comes off the playing field and flows under the fence."
In response, a spokesman for Accord said: "The situation with water running off neighbouring fields onto the gardens at the back of our properties on Billy Wright Close is a problem that Accord is aware of. We have invested in additional land drains to assist the clearance of rain water.
"Unfortunately due to the heavy rain that we have experienced recently, it appears that rain water from land adjoining our development has entered the gardens.
"Accord is working with the adjoining land owner and our customers in order to mitigate this problem.”