Background
Fleetwood was born in Saint Johnsbury, Caledonia County, Vermont to Henry W. Fleetwood and Laura Kenney Fleetwood.
Fleetwood was born in Saint Johnsbury, Caledonia County, Vermont to Henry W. Fleetwood and Laura Kenney Fleetwood.
He attended the common schools of Saint Johnsbury, and graduated from Saint Johnsbury Academy in 1886. He also entered the University of Vermont at Burlington in 1886 and graduated from Harvard University in 1891. Fleetwood studied law with his step-father, Phillip K. Gleed.
He served as a United States. Representative from Vermont. Fleetwood served as secretary of the Commission on Revision of Vermont Statutes from 1893 until 1894. Fleetwood served as prosecuting attorney for Lamoille County from 1896 until 1898.
He was elected town clerk and treasurer of Morrisville, serving from 1896 until 1900.
He was one of the presidential electors from Vermont in 1900. Fleetwood was the Secretary of the State of Vermont and the Insurance Commissioner of Vermont from 1902 until 1908.
He again served as Secretary of the State from 1917 until 1919. From 1910 until 1913 he served as a Director of the Saint Johnsbury and Lake Champlain Railroad.
Fleetwood was elected as a Republican candidate to the Sixty-eighth Congress, serving from March 4, 1923 until March 3, 1925.
He was not a candidate for renomination in 1924. After leaving Congress, he resumed the practice of law and engaged in banking. He died on January 28, 1938 in Morrisville, Vermont.
He is interred in Pleasant View Cemetery in Morrisville.
Fleetwood served as a member of the Vermont House of Representatives from 1900 until 1902.