He was the younger brother of journalist Vaughan Kester and a cousin of the literary editor and critic William Dean Howells.

Actress Annie Russell produced and starred in his 1906 Quaker tale Friend Hannah, written with the help of his brother, Vaughan.

His most successful Broadway effort was probably The Woman of Bronze, which ran for 252 performances between September 1920 and April 1921 at Manhattan's Frazee Theatre.

A few years later Kester and his mother relocated to Belmont, an estate near Alexandria, Virginia,[8] which is today part of the campus of St. Stephen's & St. Agnes School.

[1] Kester spoke of his novel His Own Country in the aftermath of World War I: The Race problem is always with us, and as my story deals in a serious way with its more serious aspects, I do not think it can be untimely.

Understanding must precede intelligent action along any lines, and my reason – perhaps I would better say my justification – for writing His Own Country has been my hope and belief that it would bring some little considered phases of this menacing and mighty problem more clearly before the minds of readers who live remote from it, yet whose consent is necessary, as it should be in a democracy, to any adjustment of settlement of living conditions where the races are existing side by side.