269 Cobourg Street was constructed between 1908 and 1909, which coincided with the development of much of this tract that became extensions of Cobourg Street, Water Street, and Ballantyne Avenue east of Front Street. It was therefore constructed contemporaneously with many residences in the neighbourhood. However, unlike many of the Foursquare style homes that characterize much of this neighbourhood, 269 Cobourg Street is an example of a cross-gabled residence-form structure that appears to be a scaled-back, vernacular form of the Queen Anne style which was becomingout of vogue by this time. 269 Cobourg Street mirrors 265 Cobourg Street, which is adjacent to the west. These houses should be regarded as a well-maintained pair that have retained historical features like wooden sash windows.

269 Cobourg Street is one-and-a-half storeys tall and has a yellow brick veneer with running bond brickwork. It has a recessed entry along the east part of the front elevation and features a pleasant front window divided with wood muntins. A semi-circular divided transom window sits above.

This house was occupied by sisters Catherine and Christina (Christena) Sutherland, the latter being listed as the head of the house in 1911. Catherine and Christina were born in West Zorra, Oxford County to Scottish-born parents Andrew and Sophia Sutherland (née McDonald). Andrew and Sophia were born in Sutherlandshire, Scotland. The couple would pass away just two days apart in August, 1905. At that time, they resided on Lot 30, Concession 14 in East Nissouri, Oxford County.

Catherine was born on February 12th, 1859, and Christina in 1863, making them the eldest of at least eight children. Not much is known about the two sisters, especially Christina. It is evident that they both worked as dressmakers. In 1896, Christina worked as a dressmaker for Abbie Sullivan whose shop was located at 52 Ontario Street (74-76 Ontario Street today). At this time, Christina boarded on the southwest corner of Avondale and Norman. Christina would pass away on December 8th, 1913.
Catherine outlived her sister by over two decades, seemingly devoting much of her life to dressmaking. Residing at 269 Cobourg until her death, she spent much of the 1920s and early 1930s as a dressmaker for Georgina Knowles. Knowles, who lived at 465 Huron Street, ran a dress making school at 6 Downie Street (the Gordon Block or Festival Square).

In 1930 and 1931, Catherine was listed as a tailor. She retired in 1932 and on March 22nd, 1934, she died of chronic bronchitis. According to land records, it appears Andrew Sutherland, the “sole surviving executor of Christine Sutherland,” was granted the house upon her death, though this may have been simply a brief handling of the estate. Directories show that Charles W. and Mary A. Stillman resided here in 1936. Charles was a representative of the Doughnut Corporation of America. Then, Robert Wood likely lived here for the rest of the 1930s and in 1940, 269 Cobourg Street was vacant.