The original Troy Hills School was located on the site of the current Troy Hills School annex. It was a one-room schoolhouse that met the needs of children back in the days when New Jersey was a British Colony.

When the community grew, it was necessary to expand the facility. A two-room building was constructed on that site. It was called Troy Academy and served the community for more than a century before it was moved in 1909 to Troy Meadow Road.

In 1928, Troy School, also a two-room facility, was built (now the annex). This building housed many grades over the years. Mrs. Spiegel, a current third grade teacher at Troy Hills School, has fond memories of teaching in that location.

The current Troy Hills School was constructed in 1966 and the "little red schoolhouse" became the annex. Eventually, in 1979, after an addition to the 'new' Troy Hills School was completed, the students from the annex joined the students in the 'big school'.