In the Fall of 1931, St. Mary, Star of the Sea School opened with the small beginning of a kindergarten through the fifth grade. The school was opened with a High Mass, and placed under the special care of Our Lady, Star of the Sea. Three Sisters were assigned to the mission, including Sister Urban who was the superior and teaching principal. The pastor, Reverend James M. Kilroe, had the Parish clubhouse on City Island prepared for the Sisters, and he arranged for the Blessed Sacrament to be kept in the convent. The auditorium was partitioned with movable dividers to separate the classes. Each year another grade was added until the school reached the full eight grades.

In 1945, at the close of World War II, not only the parish but the community as a whole mourned the death of Father Kilroe. His many acts of private charity, his priestly kindliness and his active role in the affairs of the Island, including creating the school, were recognized later with the renaming of Elizabeth Street to Kilroe Street in his memory.

Reverend Edward C. Nilan arrived at St. Mary’s in April, 1945, and is still lovingly remembered by many parishioners for his unbounded energy and drive. Many also remember his Boxer, Boots, who was often seen at Mass and in the school.

The first object of Father Nilan’s attention upon his arrival was the parish school. The old auditorium no longer met the needed space requirements for the school children due to the increase in the number of students. Enrollment had risen from thirty in 1931 to almost two hundred in 1945. Father Nilan had inaugurated a fund-raising drive whereby sufficient money was raised toward the construction of a new school. Building was begun in June 1948. The convent, originally located on the school site, was moved to Kilroe Street and a new wing added to allow for additional living quarters as well as a chapel.