Winship was born in Ottringham, Yorkshire, England on February 19, 1881 and emigrated to Vancouver, British Columbia in the early 1900s. There he met and married his wife, Catherine Glenn, also an immigrant, from Scotland. They arrived in Portland in 1913 when advertisements for his work began to appear regularly in The Oregonian and the Oregon Journal.

Over the course of his 40-plus year home construction career, Winship and his crews were  prolific, building homes through three major building booms: the mid 19-teens, and the 1920s primarily in northeast and southeast Portland; and later in post-World War II ranch-style homes, mostly on the westside.

Most of his work was on speculation: building to sell into the market and his advertisements always invited buyers to come look for themselves: “Open for inspection.” Advertisements like this caught the eye of prospective buyers:

From The Oregonian, April 18, 1928

In 1921, Winship built his own family home in Rose City Park at 2115 NE 48^th. He and Catherine raised three daughters in the Dutch colonial house that still stands. During his building career he was a leading advocate and volunteer for construction of the old Rose City Park library at NE 42^nd and Hancock, and was an active volunteer for the Oregon Humane Society. In retirement he served for 10 years as the society’s president of the board. He died in Portland on February 6, 1969.