The residence at 255 Front Street was built in 1926 by Morton Squires.

Morton Squires acquired the property in 1925 when his mother-in-law, Sarah Large, who was living at 257 Front Street, sub-divided her lot into two smaller properties. However, when the house was finished Morton, a lineman and the son of a Listowel carriage maker, and his wife, Sarah's daughter Mary, a teacher, continued to live with Sarah and the new house was rented to a young couple, Wilfred and Gladys Wilson.

Wilfred was born in Stratford, the son of Alexander and Emma Mallion Wilson and, with his sister Jessie and brother Russell, grew up here. In 1925 he married Gladys MacKay at St. Andrews Presbyterian Church in Stratford and, over the years, they became the parents of sons James and Donald. At the time of their marriage Wilfred was employed as a clerk at The Kroehler Manufacturing Company, a prominent Stratford furniture company located on the north-west corner of Ontario and Romeo streets (now the site of the Arden Park Best Western Hotel). He would spend his entire career in various positions at Kroehlers retiring in 1961 after 40 years of service. His son Donald followed in his father's footsteps as a Kroehler employee.

Although the furniture industry in Stratford began in the mid-1800s it was actually at its height during the early twentieth century when it employed about a quarter of the city's workforce. During those years there were approximately 20 furniture factories in Stratford where the city's connection with the country's main railway systems enabled furniture produced in Stratford to be quickly exported in many directions. Situated in an area with  large forests filled with trees such as oak, maple, pine, birch and other woods sought after by furniture manufacturers, the industry was second in importance after the railway operations to the city's affluence. An annual international furniture show which attracted large numbers of potential buyers became a popular event. Kroehlers was one of the oldest furniture companies in Stratford and continued in business until the early 1990s.

According to his obituary in the Stratford Beacon Herald at the time of his death in 1976, Wilfred was very active in Stratford's minor sports activities, at one point being named Sportsman of the Year. He was also involved with several church and community activities.