Windsor plantation was built in 1859 and it is said that Mark Twain used to stand in the rooftop observatory and look out over the Mississippi River. The house contained 25 rooms and 25 fireplaces and the basement housed a schoolroom, dairy and supply rooms. The rooftop observatory held signal equipment used to signal Confederate troops of Union advances.

It was used as a Union hospital during the Civil War and that's what probably saved it from being burned during the war but during a party in 1890, a guest left a cigar burning on the upper balcony and the house burned to the ground. Only a few columns and the iron staircase were left. The staircase now resides at nearby Alcorn State University.

Windsor Ruins have been featured in several movies, including Raintree County and Ghosts of Mississippi.