Based on the map of Easton in Lake, Griffing, Stevenson 1877 Atlas, a simple one-story framed house with a rectangular footprint previously sat on the property. It was during the same year of 1877 that the last will of Eliza Jane Ridgaway subdivided and sold off the parcels of Lot 50, which included what is now 208 South Street. By 1879, the trustee, J.F. Bateman, had sold a couple of these parcels to Richard John Trippe, belonging to the notable Trippe family of Dorchester and Talbot Counties. Many of Richard J. Trippe's extended family members lived in Easton, even on South Street and certainly within The Hill, including Thomas Hayward Trippe of the Richard Upjohn designed Trippe-Beale House (220 South St.), Dr. Edward R. Trippe, and Dr. Samuel Trippe. The Trippe extended family at this time was skilled in the field of medicine, including Edward and Samuel Trippe being the two local physicians and Richard John Trippe as a druggist/apothecary. Richard J. Trippe may have been in poor health as the property was sold to Joseph H. White only three years later in 1882, and then his wife Annie is recorded as a widow living in Baltimore City with their children by the 1900 Census.
Little documentation exists on Joseph H. White beyond his fighting and surviving the Civil War as a Sergeant of the Union. His work occupation during his residency at 208-210 South Street cannot be determined due to the loss of the 1890 U.S. Federal Census Records, but the associated deeds show the property was sold after he passed away in 1895. The purchaser was William Thomas Smith who lived in the easternmost duplex unit of the property along with his wife Elizabeth A. Smith and their children. The Smith family men all worked in the local brick making and masonry associated trades, which harkens to the growth of Easton's residential population as a result of the railroad and the proceeding industrialization at the turn-of-the-century. According to the 1900 and 1910 U.S. Federal Census Records, the Smith family rented the other side of the duplex to various younger working families. By 1920, William Thomas Smith's son, Joseph E. Smith, would rent this other half of the duplex until he could purchase his own house in Easton at 406 Aurora Street.