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Windsor is an incorporated town in Isle of Wight County in the Hampton Roads region of southeastern Virginia in the United States. It is located near the crossroads of U.S. Route 460 and U.S. Route 258. The population was 916 at the 2000 census. However, due to recent annexation of a portion of Isle of Wight County, the town of Windsor grew to a population of over 3000 people.
Windsor was originally in Warrosquyoake Shire which was created in 1634 in the Virginia Colony by the Virginia House of Burgesses and King Charles I of England. Warrosquyoake was named for the friendly local Native Americans, but changed a short time later to honor the Isle of Wight, a location in the English Channel. The spelling and pronunciation of the revised name were both more practical for the European colonists.
Popular legend has it that a Southampton County native, William Mahone (1826–1895), builder of the Norfolk and Petersburg Railroad (now Norfolk Southern), and his cultured wife, Otelia Butler Mahone (1837–1911), daughter of the late Dr. Robert Butler, who was raised in Smithfield, traveled along the newly completed Norfolk and Petersburg Railroad naming stations. Otelia was reading Ivanhoe a book written by Sir Walter Scott. From his historical Scottish novels, Otelia chose the place name of Windsor, as well as those of Waverly and Wakefield. She tapped the Scottish Clan "McIvor" for the name of Ivor, a small town in neighboring Southampton County. When they could not agree, it is said that they invented a new name in honor of their dispute, which is how the tiny community of Disputanta was created. The N&P railroad was completed in 1858.