From the corner of 17th Street and Princess Avenue, look west along Princess Avenue and notice the stone wall that runs the full length of the 1700 block. This wall and the one along 17th Street are the only visible clue that this block's history is different. The block was originally subdivided into twenty equal-size lots and made available for sale in 1882. Ten years later, in 1892 James A. Smart, a local merchant and political figure, purchased the four lots at the north end of the block and proceeded to have a large house built on the property. Smart arrived in Brandon in 1881 and established a hardware business. The following year he was elected to serve as alderman on the city's first council. Later, he served two non-sequential terms as mayor. Smart's political ambitions went beyond the local community. He served several terms in the provincial legislature and when Brandon lawyer Clifford Sifton was elected to Parliament in 1896, Smart moved to Ottawa to serve as Sifton's advisor. Smart's residence was appropriate for a man of his political stature. Besides a large three story brick house the property contained a separate servants' house, a stable, and a wading pool for his children.
Smart sold his property in 1899 for $4,200 to another prominent local businessman, Charles Whitehead, the man who was responsible, among other things, for having the first consignment of lumber shipped by river steamer to the new community of Brandon in May of 1881. In 1900 Whitehead purchased the remaining sixteen lots from the various owners. Shortly thereafter Whitehead hired a Scottish stone mason to construct a stone wall around the entire block. The task took four years to complete. Whitehead later passed the property on to his daughter Margaret who in turn passed it on to her son John C.P. Mitchell. In 1939 the lots south of the residence were sold; and the following year three single-family homes were built. In the late 1940s the second and third stories of the Smart-Whitehead home were removed in an effort to give the structure a more modern appearance. In 1977 the original house was sold; more recently, it was moved to the corner of Kirkcaldy Avenue and Patterson Crescent.