A native of Chicago, Grey had practiced architecture successfully in Milwaukee for several years. Instead of enrolling in a university architecture school, Grey trained as an apprentice at a Milwaukee architectural firm, Ferry & Clas. The young architect proved to be something of a prodigy, winning an architectural competition at the age of 18 for a water tower sponsored by the national publication Engineering and Building Record in 1890. He worked in the mainstream of the Arts and Crafts movement, first in the Midwest and then in California. His buildings, while varied, were firmly based in vernacular forms. He always sought simplicity of design and authenticity of materials.
During his apprentice years Grey made several bicycle trips to Europe under the tutelage of Maine architect John Calvin Stevens, absorbing both the great and the vernacular architecture of the continent and also gaining practice in sketching and water color. Throughout his life Grey would produce accomplished sketches, beautiful water colors and oils, even murals, resulting in his becoming known as an artist as well as an architect.
In 1898 Grey struck out on his own, founding his own architectural practice in Milwaukee. His first project was a summer home for himself in the developing resort of Fox Point, Wisconsin, on the shores of Lake Michigan. As Grey relates it, he had no need for a summer home, he was as yet unmarried and had no family, but he was so attrac