In 1928 the town acquired eight acres of farmland bordering the Winn Brook for school, park, or recreational purposes. Thirteen thousand dollars was appropriated for this purpose. In 1935 the Winn Brook School was built on this site with Miss Eva S. Burns as the first principal. There were 314 pupils in grades K-6, ten teachers and one janitor.

The Winn Brook School district has always included both the area immediately adjacent to the school and the Belmont Hill area. Over time, the school became crowded and an addition was added in 1958. In 1987-89 an extensive renovation and addition (including current gymnasium and library) was carried out. The new gymnasium was dedicated in 1990 to Robert L. Blaney who was principal from 1952 until 1982. Loretta Warden served as principal from 1982 until 1988. Following a year with Alice Nahabedian as Acting Principal, Douglas Weinstock became principal in 1989. Upon his retirement in 2001, the Winn Brook School library was named the Doug Weinstock Library and an amazing likeness of Mr. Weinstock, surrounded by storybook characters, was painted on one wall. Winn Brook welcomed Pattie Berkey as principal in 2001 who was followed, in 2002, by Janet Carey and then in 2020 by Anita Mecklenburg our current school principal. 

A nature study area was created at the corner of Waterhouse Road and Cross Street by Winn Brook's PTA in 1990. The school abuts Joey's Park as well as playing fields and tennis courts, which are under the auspices of the Recreation Department. In 2013, over the course of three months, over 2,000 volunteers showed up to help rebuild the park. With so many volunteers returning for their second build, many with their own children, it was a true labor of love. 

The fifth grades moved with the opening of the new Chenery Middle School in 1997.