Lovering School starts at 253 Oak Street under Lila Clary. She would live in the house. The school went by the name The Private Clary School from September of 1905 to September of 1910. (I can however only find it under Clary School in 1909 unwards.) Lila starts as teacher and then becomes a principal. The school in 1905 was started because the private kindergarten of May A Lentelle was closing. That school was at 214 Walnut Street.
The house belongs to Charles and Ettie H Richards. In early 1918 Ettie moves to 283 Maple Street but the school remains at Oak. Mary Lovering is one of the founders. Mary is the daughter of Charles Ranlet and the spouse of Ernest. Then the school moves to 50 Pleasant Street. That address would be renumbered in the year 1924 to 252 Pleasant Street. Thus it is also 250 Pleasant Street since it is a two family house.
The school might have had its name changed to Lovering when the Lovering family moved from Holyoke to Brookline.
| address | principal | starts | ends | FINDAGRAVE |
| 253 Oak Street | Lila F Clary | 1905 | 1918 | FINDAGRAVE |
| 50 Pleasant Street / 250 Pleasant Street | Doris Kimball | 1918 | 1929 | FINDAGRAVE |
| 250 Pleasant Street | Helen A Springer (later Russell) | 1929 | 1937 | FINDAGRAVE |
| Elma G Balise | 1937 | 1939 | FINDAGRAVE | |
| vacant | 1940 | 1946 | ||
In 1911 the school was still small. Students were James Ramage (age 6), May Lincoln (12), Eleanor Whitten (11), Benjamin Childs (8), William Hammond (8), Joseph Metcalf (8), and Margaret Penning (7).