A group of immigrants, from what is now Hanover, Germany, established a settlement that they named Franzosenbusch. It was located at the corner of 22nd Street and Wolf Road. The community included the Immanuel Lutheran Church, a trading post and general store, blacksmith shop, and a two-room schoolhouse built in 1852. The schoolhouse was moved to the west side of Wolf Road and was eventually converted to a farmhouse.

The Westchester Public Schools, District 92-5, was created by taking sections of Bellwood SD 88, Lindop SD 92, and Hillside SD 93. The first school board meeting was held in January 1929 when the primary order of business after electing its officers was to authorize a referendum to support the newly created school district and authorize the construction of two schools. Soon construction of the two schools began. Britten School, named after the first Board President, Grant Britten, who had also donated the land for the school and Nixon School, named after George Nixon who also donated the land. Each school had only two rooms. Britten School is currently the home of MacNeal Day School. Nixon School is now Westchester Middle School (WMS).

While the schools were under construction, students attended school at two residences on Newcastle Avenue -- each with 15 students.

During the Depression, the population of Westchester decreased as did the number of students attending school. But, when the population increased again in the early 1940s, there was a need to rent additional classroom space. The school district used the basement of a local church and then purchased the barracks that was used during World War II to house war prisoners and later to house workers of the Manhattan Project. The barracks was moved to Westchester and remodeled. It was named Romilly Hall and used as three classrooms for about five or six years. It is now the bus barn housing the District's bus fleet.

Between 1950 and 1960, Westchester grew from 4300 to 18,000 residents and the English-style homes were now surrounded by Georgians, ranches, and split-level homes. The High Ridge School, now Westchester Intermediate School (WIS), was built with 11 classrooms. In 1958, land was purchased on the south side of Westchester for the Mary Jane Kennedy School, now Westchester Primary School (WPS).

In 1972, School District 92-5 served the highest enrollment with over 2,000 students. By 1980, enrollment declined to 974 and two schools were closed: Britten and Kennedy. At that time, High Ridge became Westchester Elementary School housing Kindergarten through Grade 5. Nixon became Westchester Middle School housing Grades 6-8. Kennedy School was eventually reopened in the late 1980s becoming Westchester Primary School housing PreK through Grade 2. Westchester Elementary School changed to Westchester Intermediate School housing Grades 3-5.