History

In 1979, after ten years of teaching in public and private schools, Dalia Eisen decided to establish her own school. She believed she could better serve students and offer more than existing schools would allow. Dalia felt that children needed a school that could address their diverse learning needs through differentiated instruction, while also preserving tried and true methods for teaching the basics, including phonics, grammar, and spelling, which many public schools were beginning to abandon.

In September 1980, Crestwood opened its doors with seven students in 800 square feet of office space at Eglinton and Bathurst. Although she initially considered waiting to build enrollment before opening, Dalia ultimately decided to move ahead and trust her vision.

By 1985, Crestwood had grown to 70 students and moved into a Victorian house on Prince Arthur Avenue. In 1990, just ten years after opening, enrollment reached 360 students from Junior Kindergarten to Grade 6, and the school relocated to its current campus at Bayview and Lawrence.

From the beginning, families were drawn to Crestwood. Teachers took the time to get to know each student well and understand what each individual needed to succeed and gain confidence. Students came to love learning and were genuinely eager to come to school each day. Parents appreciated Crestwood’s thoughtful balance of innovative and traditional teaching methods, as well as its ability to provide an environment that felt both safe and adventurous. These defining qualities have remained constant over the years.

In response to ongoing interest from families, who repeatedly asked for an upper school, Dalia eventually agreed to expand. In the spring of 2001, Vince Pagano accepted the role of Headmaster of Crestwood Preparatory College (Grades 7 to 12) and worked with Dalia to launch the new program. He oversaw the renovation and expansion of a newly acquired campus, located less than 10 minutes away, near York Mills and the Don Valley Parkway, ensuring that everything was ready for the inaugural year that September. Today, Crestwood Preparatory College enrolls approximately 550 students.