The house was built for Jacob Ross Green (1810–c. 1875) from South Carolina.[3] Around 1820, his family moved to St. Clair County, Alabama.[3] In 1831, Jacob Ross Green married Elizabeth Boyd, the daughter of Judge Samuel Boyd, and soon began acquiring land in the newly established county of Benton (later renamed Calhoun County).[3] Under the Treaty of Cusseta in 1832, the United States Government acquired the entire Creek Nation land holdings, which included lands in northeast Alabama.[3] Upon petition, land patents were issued to the White settlers many of whom had recently moved to the area.[3] On April 25, 1842, O. E. Burt sold to Jacob Ross Green 150 acres (61 ha) of land and it was on the tract he built his home known as Greenwood.[3] He farmed the land and became successful, and by 1844 he had owned eleven enslaved people.[3]
Jacob Green had five children, including Samuel LaFayette Green Sr., the next owner of Greenwood starting in 1865.[3] In 1913, his son S. L. Green Jr. acquired the property.[3] Greenwood stayed in the Green family until 1916, when it was sold to his son-in-law Norris Woodruff.[3]
Woodruff lived at Greenwood for nearly 23 years, until his death in 1939.[3] Woodruff's eldest son, Wallace Green Woodruff acquired the house after his father's death from his many siblings.[3] After his death in 1963, his son Wallace G. Woodruff Jr. acquired the house, and when he died, his five children inherited the house.[3]