Apparently Stephenson County had a lot of pleasant schools, as this is one of three former Pleasant Hill schools in the county (the other two were near Dakota and Freeport). The school was located just a mile west of the Mount Pleasant School (at the current Mount Pleasant cemetery).

On March 16, 1954, the Monroe (WI) Evening Times reported that petitions were being circulated to gather support to sell the school, in order to put the decision on the April ballot for voters to decide. The school had become part of the Orangeville school district, and the board had recently decided both Pleasant Hill and Mount Pleasant to the east were no longer necessary (Freeport Journal-Standard 3/10/1954). The 1952-53 school year was likely Pleasant Hill's last, as a May 20, 1953 article in the Journal-Standard was one of the last which referred to the school as its own district. On April 10, 1954 voters officially approved the sale of the school by a wide margin.

A photo of the school as it was in 1918 is archived on the Lena-Winslow school district website:

https://www.le-win.net/ourpages/auto/...

These photos originated from a 1918-19 Stephenson County school directory. It contained photos of each school, along with the names of teachers and school board members.