Fountain Alley earned its name from the public fountain that once stood at its intersection with First Street, a gathering point in the dusty pueblo that San Jose was during the mid-nineteenth century. The alley became a commercial corridor lined with small shops, offices, and services that served the downtown community. As San Jose grew and modernized, most of the buildings along Fountain Alley were replaced by newer structures. The building at 27-29 survived, its late Victorian facade a reminder of the scale and character of downtown commerce before the automobile and urban renewal transformed the city.

The building's architectural significance lies in its uniqueness rather than its grandeur. It is the only remaining example of late Victorian commercial architecture in this section of San Jose, a style characterized by decorative brickwork, cornices, and the proportions of a merchant class that built to human scale. The structure has housed various businesses over its lifetime, each one contributing another layer to the building's history. Its survival through the aggressive development cycles of the twentieth century, when downtown San Jose was repeatedly reimagined, speaks to a combination of luck, neglect, and the eventual recognition that old buildings carry value.

The National Register listing in 1982 came during a period of growing awareness that San Jose had been too aggressive in demolishing its historic structures. The building at 27-29 Fountain Alley is small, modest, and easily overlooked, exactly the kind of structure that cities tend to sacrifice for parking lots or new development. Its preservation matters precisely because it is ordinary, a representative of the everyday commercial architecture that defined nineteenth-century San Jose. Without it, Fountain Alley would have no physical connection to the era that gave the street its name.