The Flemming house is recognized for both its architecture and its association with the Flemming family. Originally built around 1905 for R. Norman Loane, the building acts as a good example of a four-square Edwardian home. This style is evident in how the first story is supported by seven Doric columns with balustrades, as well as how the second story gallery protrudes from the rear bay.

The Flemming house was also home of J.K. Flemming during his time as the 14th Premier of New Brunswick, lasting from 1911 to 1914. His then-teenaged son, Hugh John Flemming, was raised here and attended Woodstock High School. As an adult, Hugh followed his father's footsteps in politics, eventually becoming the 24th Premier of New Brunswick (1952–1961). Additionally, in 1916, the house was acquired by James Russell Gilliland (1860–1929), Divisional Superintendent of the Canadian Pacific Rail, when he and his family moved to Woodstock.