The Montessori School of Windsor began with a study group, organized by J. Robert Charette in 1960. He studied the Montessori Method at the Teacher Training Centre in California in 1963, and opened the Montessori School of Windsor in the fall of 1966. He was the administrator as well as the Classroom Director until his death in 1974.

Patricia Charette (Mrs. J. R. Charette) became a Montessori Director after having trained at the Michigan Montessori Training Centre in 1969. She had worked closely with her husband since the school began, and upon his death became the Administrator as well as continuing as the Classroom Director.

Michelle Charette became a Montessori Director following her training in Michigan in 1977. She has been with the Montessori School of Windsor since 1970. Patricia retired in 1989 and Michelle became the School Administrator, as well as continuing as the Classroom Director. The Montessori School of Windsor currently operates a preschool program at the Bellewood site. The Bellewood site offers pre-school and before and after pre-school programs. The school continue in the same spirit in which they began in 1966 with Mr. and Mrs. Charette, providing quality education to preschool children.

All the staff at Montessori are qualified teachers who love the children and have been devoted to the school for many years. All teachers have valid CPR/FIRST Aid training, Police Clearances, and Food Serving Certificate. Teachers also take part in education seminars to continue learning.

Pauline Vernuccio is an outstanding teacher and supervisor; she has been with the Montessori School of Windsor since 1987.

Jeanette Dias Hardy joined the school in 1994 as a creative classroom teacher and in 2008 became a supervisor.

"Our aim is not only to make the child understand, and still less to force him to memorize, but so to touch his imagination as to enthuse him to his innermost core." - Maria Montessori

"These words reveal the child's inner needs: "Help me to do it alone." - Maria Montessori