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History & Facilities


The Winston School San Antonio was founded in 1985 by Mrs. Maggie Sheerin and Dr. Mark Weinstein. It began as an extension of The Winston School in Dallas, providing academic programs for San Antonio students with learning differences in grades 1-5. Since then, it has grown in both size and scope and has amicably severed its ties with The Winston School Dallas.

Photo of Dr. Charles J. Karulak - Headmaster 1989-2021
Dr. Charles J. Karulak - Headmaster 1989-2021

In spring of 1989, Dr. Charles J. Karulak agreed to a one-year interim position as Head of School. Well, his one year interim headship became a 32-year career. When Dr. Karulak started as Headmaster in July of that year, he soon encountered numerous challenges that required his immediate attention in order for the school to remain a viable organization. Some of those challenges included a large debt owed to Winston-Dallas as a result of opening the San Antonio campus, completing application and preparation for accreditation, the school’s third move in five years, and a projected loss in income due to low enrollment.

Class of 1990 Winston's First Graduating Class
Class of 1990 - Winston's First Graduating Class

By the end of his first year, WSSA had earned accreditation, retired almost a quarter of the debt, held its first ever graduation, and ended the year with no deficit. During his second year as Head of School, he suggested to the Board that WSSA’s next move should be to a permanent site. For nine years, WSSA leased a school building while making plans for a capital campaign for a new campus designed for the needs of our students.

Photo of the Original Campus
Original Campus

In February of 1994, WSSA was granted an eighty-year lease of just under 16 acres in the South Texas Medical Center by the San Antonio Medical Foundation. During the next four years, funds were raised to build the campus and at the end of the 1997-98 school year, we moved to our permanent home (all belongings were moved in one day) and even had a summer school program. It was an ambitious start to our new home.

photo of the Current Campus
Current Campus

The new campus was adequate, but it did not include spaces identified to improve and expand learning opportunities for current and future students. In 2014, the Board decided to embark on a second major capital campaign to add needed classrooms. In August 2020, a new additional building opened affording our students those new opportunities. In thirty-two years, WSSA’ s net worth went from a negative amount to over $19 million including a modest endowment.

Fine Arts Building and Assembly Hall
Fine Arts Building & Assembly Hall

The newest addition to the WSSA campus is the Greehey Fine Arts Building & Assembly Hall. This building includes a dining & assembly hall, a black box theater, music studios, several art studios, an expanded media lab, a welding and woodworking shop, and many other features.

photo of the Learning Center
Learning Center

The Learning Center consists of 28 classrooms, an administrative office suite, a library, and copious storage space. While all students have classes in the Learning Center, the building is segmented into Lower, Middle, and Upper School sections.

Photo of the Gym

The school gymnasium is used by students in grades K-12, and features hardwood floors, three locker rooms, and a kitchen and concession area. If you are an organization or sports team interested in renting Winston's gym space, please contact


In 2013, a new playground was constructed through the generosity of our community members and the Kingdom for Kids program.