The house at 38 Earl Street was built in Fall 1872 - Spring 1873 by John Oliver (“Olver” in some records), a teamster (a driver of horses). It appears that John was born about 1835 in Oxford County, where his father Nicholas Oliver was a farmer. Nicholas and his wife were both born in England and probably emigrated to Upper Canada just before John’s birth. John was the oldest of at least three children.

In the 1851 Census, John is listed as a labourer living with his family in Oxford County. By 1861 John had married Catherine (maiden name unknown), who was born in 1833 in Upper Canada or Scotland, and they were living in Stratford, where John continued to be listed as a labourer. By 1867 the directory for Perth County lists John as a teamster, and he and Catherine along with their son John Alexander were living on William Street. John was listed as a teamster until 1885 when he is described as a labourer, but in 1891 he is listed as a teamster again.

All of the available directories list John and his family as living on William Street from 1867 to 1885, although the tax assessment rolls state that he was living at 38 Earl Street in 1875. It is possible that John built 38 Earl as a rental property. The first occupant of the house was George Williams, a carpenter, who, may have been living there in order to complete the construction. George was born in Pennsylvania around 1836, eventually emigrating to Canada where he married Margaret, born in Ontario. They had at least seven children.

Perhaps John was living there in the third year of his ownership because he was completing the construction. In any case, the house was sold to Abraham Greenwood, a labourer, in 1876.

John and Catherine had one son, John Alexander, born around 1865. It appears that he moved to New York State. John’s father, Nicholas, appears to have moved to Stratford by 1861. He died in 1870 and was buried in Dunn’s Bridge Methodist Cemetery, near present-day Lorne and O’Loane.

Catherine Oliver died September 3, 1882. John Oliver died November 4, 1895 from typhoid fever. Both are buried in Avondale Cemetery.

The lot where 38 Earl Street is located was owned by Robert Myers, one of the first boot- and shoemakers in Stratford, with a shoe factory on Downie Street. From 1881 to 1891 James Wright, a butcher who had a shop at 41 Market Place, lived at 38 Earl Street. The house was substantially enlarged and turned into a rental property around 1891 by James Stamp, a contractor and mayor of Stratford.