The properties at 185 and 187 College Street have design value as surviving examples of late 19th century house form buildings on College Street, west of McCaul Street, with detailing from the popular architectural styles of the Victorian era, including the Italianate and Gothic Revival.  Anchoring the west end of a trio of semi-detached house form buildings that were constructed together, the pair is further distinguished by the surviving decorative wood detailing in the gables.
Contextually, the properties at 185 and 187 College Street are valued for their role in defining, supporting and maintaining the historical character of College Street, west of McCaul Street, which originally developed as a residential neighbourhood.  With their later conversion for mixed commercial and residential uses, the buildings reflect the ongoing evolution of the thoroughfare.
The buildings at 185 and 187 College Street are historically, visually and physically linked to their setting in the block on the south side of the street where they are part of a series of complementary late 19th century house form buildings adjoining both sides of the intersection with Henry Street.