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An earlier hotel, the "Waldorf Astoria," occupied this site before the Earthquake and Fire of 04/18/1906; the conflagration gutted the hotel's interior, leaving only exterior remnants. The MacDougall Brothers--George and Benjamin--architects, designed this new, five-story, brick hotel building, completed in 1907, incorporating some remaining elements of the Waldorf. The San Francisco Planning Department indicated in its review of the hotel: "In the 1906 disaster, the building on this site, the Waldorf Astoria, was completely gutted, and its rear wall was partially destroyed. The McDougall Brothers, architects of record, petitioned 'to rehabilitate it to its former state.'Noting that although it was 'strongly built and well constructed in every detail,' they proposed additional reinforcement. The document notes that the original terra cotta cornice was intact, and would be retained. Implicit in the petition is an emphasis on the value of the building, even as a shell." (See "Preservation," San Francisco Property Information Map,Accessed 03/11/2013.) The MacDougalls added onto the original Waldorf perimeter, attaching a 25-foot by 75-foot annex, with the same design and dimensions, creating a new light court. John Boyd owned the hotel originally.

The Oakwood Hotel occupied a 3,746 square-foot lot, located northwest of the US Mint just across the street. According to the San Francisco County Assessor, the Oakwood Hotel had a taxable value of $2,853,047.00 in 2013. A writer for the San Francisco Planning Department described the hotel: "The well-proportioned, slender brick structure has a three-part composition. The commercial base has been largely remodeled, probably in the 1930s. The three story-shaft, sheathed in in buff brick, has enframed window bays of intricate detail, in a contrasting dark brown finish. The integrated fire escapes are also intricatelyornamented. The attic story supports the fine, pre-1906 terra-cotta cornice that the McDougall Brothers labored to preserved. The lobby, entered by a recessed, marble-trimmed vestibule, has marble walls, tiled floor, and a cofferef ceiling with molded cornices. The building is largely intact as built in 1907." (See "Preservation," San Francisco Property Information Map,Accessed 03/11/2013.)

An alteration occurred to the retail storefront on the first floor in 1935.