Windham was part of Londonderry until after 1792 and was "duly organized" in 1796. The first settler of what was to become the village was Benjamin Pierce circa 1783. Pierce was from Westmoreland, New Hampshire. f Being such a small and dispersed mountain village, relatively few men from Windham served with the Union Army during the Civil War. Windham County itself contributed heavily to manning the 4th Vermont Infantry and most of the village's sons joined either Company C or K of that regiment. The 4th regiment saw heavy combat throughout the war. One of Windham's soldiers, Captain Charles G. Gould of Company H, 5th Vermont Infantry, won the Medal of Honor for bravery under fire.
As of the census of 2000, there were 328 people, 150 households, and 91 families residing in the town. The population density was 12.6 people per square mile. There were 354 housing units at an average density of 13.6 per square mile. The racial makeup of the town was 96.04% White, 0.30% African American, 0.30% Asian, 0.91% from other races, and 2.44% from two or more races. Hispanic or Latino of any race were 1.22% of the population. There were 150 households out of which 21.3% had children under the age of 18 living with them, 52.0% were married couplesliving together, 3.3% had a female householder with no husband present, and 39.3% were non-families. 33.3% of all households were made up of individuals and 12.0% had someone living alone who was 65 years of age or older. The average household size was 2.19 and the average family size was 2.76. In the town, the population was spread out with 19.2% under the age of 18, 8.5% from 18 to 24, 25.3% from 25 to 44, 24.7% from 45 to 64, and 22.3% who were 65 years of age or older. The median age was 43 years. For every 100 females, there were 115.8 males. For every 100 females age 18 and over, there were 117.2 males. The median income for a household in the town was $39,659, and the median income for a family was $41,786. Males had a median income of $27,500 versus $23,125 for females. The per capita income for the town was $20,704. About 2.2% of families and 6.3% of the population were below the poverty line, including 8.7% of those under age 18 and 4.9% of those age 65 or over.
