3385 Upper Terrace is as an outstanding representative of the type of estate to be found in the 465 acre (188 hectare) planned residential subdivision of Uplands. Formerly part of the Hudson's Bay Company's Uplands farm, this land was developed during the pre-First World War boom days. John Charles Olmsted of the internationally recognized firm of landscape architects, Olmsted Brothers of Brookline, Massachusetts, designed Uplands as a subdivision for the wealthy. Curving streets, large estates, abundant landscaping, underground services, and architect-designed residences are the hallmark of this subdivision which was the first of its kind in Canada, and which has had a profound influence on planning other subdivisions of large homes for wealthy clients. Rigid building codes and landscape restrictions have ensured that Olmsted's ideals have been maintained.

The heritage value of 3385 Upper Terrace, built in 1912, is associated with its architect, Douglas James (1888-1962), one of two English-born and trained brothers who had a substantial impact on architecture in British Columbia. In 1907 James worked for Samuel Maclure as a draftsman and assistant on Hatley Park for which he undertook hundreds of drawings and several site inspections a week. He and his brother P. L. James formed the firm James and James in 1910. The brothers lived in Oak Bay, and received several commissions from the Municipality including the Oak Bay Municipal Hall (1912 – now demolished), St. Mary’s Church on Elgin Street (1911 – now demolished) and the Oak Bay Grocery (1912), along with other residential and school commissions until the outbreak of the First World War. Douglas James joined the Canadian Army and was sent to Duncan, BC, for training. He served in France and was discharged with the rank Lieutenant. He returned to Duncan and opened an architectural practice, completing over forty-five commissions including the campus plan and a number of buildings at Shawnigan Lake Boys’ School. He moved back to Victoria in 1938 and, in collaboration with H. C. Savage and D. C. Frame, undertook the design for Victoria’s Memorial Arena. In the late 1990s Victoria architect Pamela Charlesworth was commissioned to rehabilitate the interior which contains much of its original carved woodwork.

3385 Upper Terrace is as a fine representative of Tudor Revival architecture, a popular residential style in the early part of the twentieth century. Distinguishing elements of this style which are evident in this house include the steeply-pitched gabled roof with multiple cross-gables; an emphasis on the vertical - achieved with the rich textural change in exterior materials, such as stone foundation, stucco and half-timbered upper storeys; Tudor arches in the porte-coch_re; and prominent, decorative masonry chimneys.

This 1912 residence has been protected under a heritage covenant since 1988.