Windsor Academy began as a part time nursery school in a small rented building in New Windsor. It had a different name and was founded by two women who had taught in local daycare programs for a number of years. In 1995, this small group moved to a larger building, began renovations and planned expansions into other age groups.

In 1996, Rita Epstein was hired to create an elementary school program for this fledgling school, and in 1998, she became a partner in what was now called, Windsor Academy Educational Campus. Rita Epstein is now the sole owner and director of Windsor Academy. The building is on the site of the old Windsor Estate property on Route 94 in New Windsor.

The campus now includes three buildings, employs over forty people and serves the needs of about 150 students and their families. The school is an integral part of the community and what once started as a small nursery school among many others in the area, is now a contributing member in the educational, cultural, and social needs of residents in Orange, Ulster, and Dutchess Counties.