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Madame Henriette D. Neal, a native of France, founded the school in 1961 as a one-room preschool at St. John's Lutheran Church in Kailua. It was known as Le Jardin d'Enfants (The Garden of Children). The following year, the school added a kindergarten class and adopted the Spalding Method of Phonics, a key program feature which continues to this day. Madame Neal provided special instruction in the French language.During the next eight years, a new grade was added nearly every year. By 1968, the school went through grade 6 and had an enrollment of more than 100 students. Prior to Madame Neal's death in September 1973, Mrs. Dorothea Ralston, a teacher at the upper grade levels, provided leadership for the school until the new director, Mrs. Tallulah Bennett was appointed in the fall of 1973. Mrs. Bennett directed the school for two years.

In 1975, James M. Taylor became headmaster. Prior to coming to Le Jardin Academy, Mr. Taylor had been in administration at the Choate School in Connecticut and had been headmaster for some twenty years of Hawaii Prepatory Academy on the Big Island.By the time of Mr. Taylor's appointment in 1975, the school had grown in size to 195 students. In the years immediately following his appointment, Le Jardin became more permanently housed in the leased facilities of three contiguous churches on Kailua Road: St. John's Lutheran, Kailua United Methodist (1976), and Kailua Baptist (1981). During 1977-78, Le Jardin added a 7th grade which was followed a year later with the addition on an 8th grade. Within the first six years of Mr. Taylor's leadership, the school enrollment doubled, going from 195 in 1975 to 399 in 1980.Steven E Switzer, one of the preeminent independent school heads in the country, was appointed headmaster in July 1985. Mr. Taylor became headmaster emeritus. Mr. Switzer was the founding head of the Episcopal Day School in Jackson, Tennessee. He served as president of the board of directors of the Hawaii Association of Independent Schools from 1990-1992.

Currently, Le Jardin Academy has grown with the Windward community from grades Pre-Kindergarten to 12th. Students receive a balanced education with personal attention as they prepare for the "unfolding journey of their lives". Le Jardin opened its doors to their new, permanent campus at the site of the former Kailua Drive-in on August 30,1999. Facilities include 48 classrooms, offices, state-of-the-art computer laboratories, a computer network infrastructure, two libraries, two music and foreign language rooms, two sports fields, and a scenic lookout overlooking the Kawainui wetlands. In October of 2009, Le Jardin Academy celebrated the opening of the Charles B. Wang Gymnasium.

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