The establishment and election of Sheriffs for their respective district is found in Chapter II "Plan or Frame of Government" Section 50 of the Constitution of the State of Vermont.

Listed are the Elected Sheriff's of Windsor County, State of Vermont to present:

• 1781 - Briant Brown (Windsor, Vermont) was the first elected Sheriff of Windsor County but resigned immediately after to become a Windsor County Clerk.
• 1781-1782 - Ebenezer Brewster (Dresden, NH) was appointed to replace Briant Brown.
• 1782-1787 - Benjamin Wait, Windsor
• 1787-1790 - Paul Brigham, Norwich
• 1790-1796 - William Sweetser, Windsor
• 1796-1798 - Lucius Hubbard, Chester
• 1798-1802 - William Rice, Woodstock
• 1802-1810 - William Strong, Hartford
• 1810-1814 - Pascal P. Enos, Windsor
• 1814-1815 - Amos Heald, Chester
• 1815-1820 - Solomon W. Burke, Woodstock
• 1820-1830 - Asaph Fletcher, Jr., Woodstock
• 1830-1834 - Lysander Raymond, Woodstock
• 1834-1837 - Daniel Bowen, Weathersfield
• 1837-1839 - John Pettis, Windsor
• 1839-1842 - Joel Lull Jr., Windsor
• 1842-1844 - Zenas F. Hyde, Cavendish
• 1844-1845 - David Bosworth, Bethel
• 1845-1850 - Gilman Henry, Woodstock
• 1850-1868 - Lorenzo Richmond, Woodstock
• 1868-1880 - Surrey W. Stimson, Ludlow
• 1880-1884 - Rollin Amsden, Windsor
• 1884-1888 - Gardner J Wallace, Bethel
• 1888-1892 - Wilson S. Lovell, Springfield
• 1892-1896 - Lester C. Howe, Ludlow
• 1896-1900 - Romaine A Spafford, Springfield
• 1900-1904 - Daniel C. Jones, Royalton
• 1904-1906 - Henry H. Peck, Hartford
• 1906-1910 - Eugene A. Thomas, Woodstock
• 1910-1916 - James H. Kiniry, Windsor
• 1916-1921 - James McDonald, Ludlow
• 1921-1929 - Wallis Fairbanks, Springfield
• 1929-1947 - Ernest H. Schoenfeld,Springfield
• 1947-1975 - Melvin W. Moore, Springfield
• 1975-1979 - John T. Goode, Woodstock
• 1979-1995 - Michael Chamberlain, Woodstock
• 1995-1999 - William G. Heinz, Weathersfield
• 1999-2023 - Michael Chamberlain, Woodstock
• 2023-Present - Ryan Palmer, Windsor

The Sheriff's Department is housed in the old County Jail/State Prison in Woodstock. The Facility no longer houses prisoners. It closed it's doors in 2002 and became the home of the WCSD in 2003. 

By MATT SMITHWICK RUTLAND HERALD

Southern Vermont Bureau WINDSOR — The prison in Woodstock will finally close its doors Monday, when the Windsor prison begins accepting short-term prisoners in its new holding cells. Officials at the Southeast State Correctional Facility in Windsor met with local law enforcement officials Friday to show the facility’s just-finished holding cells, which can hold up to eight short-term prisoners. A former recreation area at Windsor was converted to holding cells when it was decided earlier this year that Woodstock’s 65 year-old prison would close. The facility in Woodstock stopped housing full-time prisoners in March, but it has been operating recently as a holding cell for those awaiting arraignment. Now Windsor has the capability to temporarily hold those prisoners. “These holding cells are merely to be used for local law enforcement so when they arrest somebody, they don’t have to drive to Rutland or St. Johnsbury,” said William Soule, interim superintendent at the Windsor jail. He said the Windsor facility would serve as the temporary lockup for Windham, Windsor and Orange counties. People arrested in those counties could be lodged at Windsor until they are arraigned. If they must remain in jail after a court appearance, they will be transferred to another facility, Soule said. The Windsor prison’s regular population consists of about 100 inmates. Most of that population is made up of sex offenders, Soule said. The facility is minimum security. The temporary prisoners won’t interact with the general population in Windsor, Soule said. Most stays will be a day or two, with some weekend stays until arraignment on Monday. “These people are only going to be housed here until they go to court and they’re arraigned,” Soule said. The $60,000 renovation job at Windsor was a kind of compromise. When it was announced that the Woodstock Regional Correctional Facility would close, police thought they would have to take prisoners to holding cells in Rutland or St. Johnsbury. Those trips would have driven up overtime and transportation costs, so part of the Windsor jail was converted for temporary prisoners. Officials plan to make use of those temporary cells until the 350-bed medium-security prison in Springfield is completed. The Springfield prison is under construction and is expected to be finished in late 2003. Springfield Police Chief Douglas Johnston attended the meeting Friday at the Windsor facility, and said the holding cells there was a good temporary solution. Taking prisoners to Rutland or St. Johnsbury would have run costs up, he said. The Springfield department uses off-duty officers to transport prisoners, Johnson said, in an effort to keep working officers in town. “It cuts down on travel time. ” The Woodstock jail, located in downtown Woodstock, is the oldest and least efficient in the state system, and the cost of housing 75 inmates there is expensive. The original plan was to keep it open until the new Springfield prison was completed. But the early closure is part of the Corrections Department’s plan to save several million dollars over the next two years. Like a number of other law enforcement officials, Johnston says that closing Woodstock prior to the opening of the Springfield prison is a mistake. Fewer prison beds in the state means more people who should be locked up will be walking the streets and committing crimes, he said. “We’re going to pay for it later on because the crime rate is going to go up in the community,” Johnston said.