372 College Street was constructed in 1887/1888. Prior to 1890, 372 College Street was known as 172 College Street. 

372 College Street was originally a semi-detached house. Its west half (374 College Street) was demolished and replaced with the extant 2-storey building during the 1970s.  

The property at 372 College Street has design value as a surviving late 19th century house form building on College Street that displays detailing from architectural styles popularized in the late 19th century, including the Second Empire and Queen Anne Revival style as indicated by the mansard roof and the distinctive bay window with the shingled cladding and the conical roof. Contextually, the property at 372 College Street is valued for its role in defining, supporting and maintaining the historical character of College Street west of Spadina Avenue, which retains its character as a “Main Street” identified primarily by its late 19th century commercial buildings, as well as house form buildings converted for commercial purposes, which set the standard for the scale and setbacks along the thoroughfare. The building at 372 College Street is historically, visually and physically linked to its setting on the north side of the street midway between Brunswick Avenue and Borden Street, where it is adjoined to the east by a group of late 19th century commercial buildings that share its scale and setback.

372 College Street was first home to Alice Stovin and Julia Stovin who operated a ladies school from the property. The school was known as The Misses Stovin's Boarding and Day School for Young Ladies; Miss A. Stovin's School; and/or The Chateau. Alice Stovin (born 1852) and Julia Stovin (born 1857) were sisters. The Stovins were originally from England and members of the Church of England. Mary Ely (born 1868) was an Irish domestic worker that also lived on site with the Stovins. The school was in operation at 372 College Street until 1897. 

Between 1913 and 1924, 372 College Street had a commercial storefront addition added to its College Street (south) elevation. The prominent turret of 372-372A College Street was reclad with the extant black medal siding in 2020.  

Various other occupants and uses of the property include: 

1900: William H. Doel, Jr. - a clerk at the European Exporters' Association.

1910: Eugene G. Lemaitre and family. Eugene G. Lemaitre was a druggist, with his pharmacy based at 256 Queen Street West. Eugenia, Harriette, and John F. Lemaitre were other members of the family that lived at 372 College Street. John F. Lemaitre also worked as a druggist at the family's pharmacy. 

1915: James A. Mumby - auctioneer; and the upstairs was home to Joseph Keating and Robert J. Lewis.

1920: Madame May, Clothes Dealer; and John May

1930: Y. H. Dawson 

1940: The College Meat Market and Bellevue Shoe Repair, with 4 upstairs residential apartments.

1950: Manor Jewellers, Figaro Barber Shop, and Sam's Shoe Shine; with 4 upstairs residential apartments.

1960: Shafer's Watch Repair and Figaro's Barber Shop; with 4 upstairs residential apartments. 

1969: Shafer's Watch Repair; with 4 upstairs residential apartments, 2 of which were vacant.

Since 2006, 372 College Street has been home to Kaisar House (Kaisar Guest House). The Kaisar House (Kaisar Guest House) is a guest house, hostel, and hotel that operates on the upper floors of 372 College Street.

As of mid-August 2021, the ground floor commercial unit of 372 College Street is home to Ragdoll Vintage. 

(Research Adam Wynne)