This ca. 1912-1914 photo is courtesy of Ken Heleba. This school is known as the Chippenhook Schoolhouse.
Details from the 1976 historic survey for this ca. 1808 (or 1876) building can be found at the link above. The structure was owned by William Russell at the time of the survey. See the Two Chippenhook Schools or Three? entry in this collection for information on the controversy dating this school.
This undated photo (below) was included as part of an unsuccessful 1981 attempt at getting the structure placed on the National Historic Register. The condition of the structure is noticeably better than the 1912-1914 photo. Notice that there was one less window. The girl in the back 3rd from the left is Alice Keyes (1893 - 1975).
The photo below is from the mid-1970's when the school was converted into a residence. It had functioned as a school from 1808 until 1970. A fire in 1973 destroyed the original rear portion of the structure. The conversion to a residence included adding the new section in the rear shown in the photo. That addition was removed when the school was relocated from across the Chippenhook Ballfield to its present location in 1978. A new rear ell was added after the relocation.
This 1981 photo was part of the National Historic Register application. Restoration efforts were still underway.
This last photo is courtesy of Ken Heleba taken in 2017.
This photo is ca. 1988 from town records.