Breakwater School was founded in 1956 by Eleanor and Frank Costa as Playtime Haven, a daycare that initially served three infants and three toddlers from the Portland area. The need for daycare in Portland was great at the time, particularly for underprivileged children, and the center quickly outgrew the space available in the Costas’ home.
In 1958, Playtime Haven moved to a bigger house in South Portland where its enrollment grew to over 80 children, ranging in age from infants to five-year-olds. There were no formal standards for daycare centers in the 1950s, and the Costas became instrumental in helping to write such standards over the years. They also pioneered a number of daycare features, such as offering transportation to and from the center and providing a registered nurse on staff.
By 1963 the Costas outgrew their space again and moved to 81 Pine Street in South Portland, where they stayed for 10 years. While at this location, program offerings expanded to include a Kindergarten and 1st Grade grounded in the Montessori philosophy. This set the cornerstone of Breakwater’s continuing reputation for offering an innovative and excellent curriculum.
During the early 1970s, the demand for daycare services declined and Breakwater focused increasingly on school-age children. In 1973, Breakwater formally incorporated as a non-profit school. It continued to serve a wide range of families, including children with diagnosed learning disabilities, long 
before “mainstreaming” became a national norm. By the late 1970s, Breakwater was offering programs for four-year-olds through 6th grade, while maintaining a Montessori “flavor”.
As state building codes evolved, the Costas began to search for a mo
re appropriate permanent location. After a series of short-term moves, the school relocated to the Cottage Farm School in Cape Elizabeth, and then in 1982 acquired the former Chapman School from the City of Portland and moved into its present location on Brighton Avenue. The Costas formally retired from Breakwater in 1985, but have continued to participate in a number of school events each year since then.
During the 1987-1988 school year, the school enrolled 135 students and purchased the adjacent Glenwood Square Baptist Church building. After renovation, it became what we call the Jessie Bullens-Crewe building today.
In 1997 the school began a capital campaign to fund a facilities expansion, which was completed in 1999. The Costa Wing, as it is now called, added four classrooms, a spacious and bright library, and an elevator to the school's main building - making it handicapped accessible for the first time.
The school also acquired the adjacent "Vacuum Cleaner" building on the corner of Capisic St. and Brighton Ave, and in 2003 tore it down and began construction of our new multi-purpose building. This building was occupied in June, 2004 and named after Daniel N. Crewe in honor of his long service and many contributions to our school.
Heads of School
El and Frank Costa 1956 – 1978
Anne-Mayre Schroeder 1978 – 1987
Interim team 1988 – 1989
Peter Wolinsky 1989 – 2001
Corny Jones 2001 – 2003
Dick Barbieri, Interim 2003 – 2004
Cesca Gallucio-Steele 2004 – 2005
Peter Buckley, Interim 2005 – 2007
David Sullivan 2007 – Present
