Virginia’s Southside plantation houses are either formal works of architecture such as Prestwould and Berry Hill, or houses that started modestly and evolved to meet subsequent needs. Among the latter type is Sunnyside, a multi-sectioned homestead, the earliest part of which was built in 1833 for Samuel and Eliza Hester on property inherited from Eliza’s father, Robert Greenwood. To their simple, three-bay, side-passage dwelling, an I-house section was added following Tucker Carrington’s acquisition in 1836. Carrington was a local politician and businessman, as well as a developer of the Mecklenburg County town of Clarksville, where Sunnyside is located. In the 1850s, the I-house section was enlarged with one-story wings, possibly executed by area builder Jacob W. Holt. Following the Civil War, Carrington’s four daughters, Agnes, Emily, Isabella, and Mildred, opened a school for young ladies at Sunnyside. Their school welcomed day students as well as boarders from Virginia and beyond. The Sunnyside School closed in 1908.  In the 21st century, the property has operated as The Sunnyside Sisters Bed and Breakfast.