It was listed as a contributing element (element #290) in the South Columbus Historic District, which was placed on the National Register in 1982. When that district was resurveyed and enlarged as the South Columbus Historic District Amendment No. 2 (which was added to the National Register 29 September 2021) this house was included in the enlarged district as element #397 (previously listed/contributing).

It was designated a Mississippi Landmark, at the request of the owner, on 29 April 2016.

The Ole Homestead is a vernacular raised cottage that was constructed between 1819 and 1829, most likely in 1825 by Charles Abert.

It was originally two rooms over two rooms facing Franklin (now 3rd) Street South and the Tombigbee River. Charles Abert is the first record owner of the property and appears to have either purchased or built the house in 1825. H. S. Bennett was a renter living in the house from 1830 - 1835. He later represented Mississippi in Congress. It was purchased from Abert in 1835 by John Kirk. He added an east wing and reoriented it to Washington (now College) Street. It is one of the oldest raised cottages in Mississippi and is probably the oldest one surviving north of the old Natchez District. It is the oldest building known to have survived within the original town limits of Columbus.

Its first owner of record was Charles Abert, a merchant who wrote in 1860 that he had moved to Columbus in 1825. His business did very well form the beginning but really seemed to mushroom in 1826. In that year records of the Choctaw Indian Agency begin to show Abert selling goods to the agency. The next year, 1827, Abert built a large brick residence on Main Street a block north of the Ole Homestead.

Though Abert moved to his new residence, he did not sell the Ole Homestead until 1835.

For three years there are no records of what was happening at the Ole Homestead. Then in 1830 it was being rented to Hendley S. Bennett a local lawyer. He lived in the house from 1830 to 1835. Bennett, a lawyer, became a Circuit Judge in 1838 and in 1854 he was elected to congress. When Abert sold the house to John Kirk in 1835, Bennett bought other property and moved.

Timing that makes one wonder if in 1827 Abert knew from his dealings with the Choctaw Agency that preliminary land cession treaty negotiations were under way and land prices would sky rocket after a treaty opened Indian lands west of Columbus. Renting the house until then would make the house a solid investment and in fact the house was sold during Indian Removal after the Choctaw and Chickasaw treaties and when Columbus was filling with land speculators. Circuit Court records indicate that Kirk enlarged the house in 1835.

Dr. James W. Hopkins purchased the house in 1859 from Lowndes County Sheriff James Wynn who had purchased it in 1846. When the Civil War erupted and Columbus became a major hospital center, Dr. Hopkins served as a surgeon at the Confederate Hospitals in Columbus.

Dr. Hopkins' son E R Hopkins was a small boy during the War. He recalled troops marching along College Street to and from the Steamboat landing on the river. He wrote of trading food with the soldiers for souvenirs. In working on the Ole Homestead Dan Clark found what may have been one of his prizes. It was a Confederate Archer type artillery shell.

About 1880 an interior wall was added making a hall between the original main floor west rooms and the windows on the main floor were replaced with 2 over 2 sashes. A south east addition and deck were added in 1952.