| Year | Won | Margin | Democratic | Republican | Total |
|---|---|---|---|---|---|
| 2024 | D | 24,687 | 11,008 | 37,350 | |
| 2020 | D | 23,376 | 9,971 | 34,446 | |
| 2016 | D | 17,556 | 8,605 | 29,928 | |
| 2012 | D | 19,494 | 8,598 | 28,699 | |
| 2008 | D | 21,444 | 9,084 | 31,165 | |
| 2004 | D | 18,561 | 11,491 | 30,767 | |
| 2000 | D | 15,140 | 11,713 | 29,147 | |
| 1996 | D | 14,070 | 8,015 | 26,023 | |
| 1992 | D | 13,871 | 9,035 | 29,192 | |
| 1988 | R | 12,009 | 12,584 | 24,930 | |
| 1984 | R | 9,869 | 14,054 | 24,247 | |
| 1980 | R | 8,067 | 10,470 | 22,903 | |
| 1976 | R | 8,282 | 11,001 | 19,716 | |
| 1972 | R | 6,989 | 12,421 | 19,532 | |
| 1968 | R | 6,986 | 9,795 | 17,347 | |
| 1964 | D | 12,163 | 5,859 | 18,023 | |
| 1960 | R | 6,250 | 12,657 | 18,909 | |
| 1956 | R | 3,820 | 14,157 | 17,982 | |
| 1952 | R | 3,791 | 13,941 | 17,769 | |
| 1948 | R | 3,736 | 9,626 | 13,568 | |
| 1944 | R | 5,089 | 9,930 | 15,019 | |
| 1940 | R | 5,475 | 9,109 | 14,612 | |
| 1936 | R | 5,084 | 9,489 | 14,622 | |
| 1932 | R | 4,343 | 9,353 | 13,927 | |
| 1928 | R | 2,747 | 10,739 | 13,515 | |
| 1924 | R | 1,015 | 10,223 | 11,560 | |
| 1920 | R | 1,714 | 8,400 | 10,175 | |
| 1916 | R | 2,216 | 4,236 | 6,563 | |
| 1912 | R | 1,302 | 2,409 | 6,427 | |
| 1908 | R | 907 | 4,683 | 5,738 | |
| 1904 | R | 797 | 4,830 | 5,768 | |
| 1900 | R | 943 | 5,227 | 6,204 | |
| 1896 | R | 674 | 6,128 | 6,962 | |
| 1892 | R | 1,329 | 4,753 | 6,190 | |
| 1888 | — | — | — | — | |
| 1884 | — | — | — | — | |
| 1880 | — | — | — | — | |
| 1876 | — | — | — | — |
Windsor County spans the upper Connecticut River valley and delivered a 35-point Democratic presidential margin in 2024, reflecting Vermont's broader shift away from its historic Republican lean over the past three decades.
The Democratic margin in Windsor County reached its widest at forty points in 2008. The margin in 2024 was thirty-seven points — still decisive.
Windsor County's loyalty is rooted in its place. Median household income of $77,594, a 93% non-Hispanic-white share, and a population of 57,990 together describe a community whose political habits are deeply settled. The county's voting pattern over the last decade is most similar to that of Addison County and Washington County.
