Real estate, cotton, and oil were three of the most important industries fueling the economic boom of the 1920s. One man who used all three to his best advantage was N. Bert Smith, who lived in this two-story frame home from 1924 to 1929.

Smith, a native of Kentucky, settled in the Indian Territory in 1900. He worked in a general store and attended business college, then entered the cotton business in Holdenville and Wewoka. Meanwhile, he bought land, thousands of acres considered to be of little value. In 1923, when oil was discovered on that land, Smith suddenly found himself in the oil business.

After moving into the house on 21st with his wife, Willie, Smith purchased the Oklahoma Life Insurance Company. They later moved to a larger house on 17th.

Other longtime occupants in the home have been Mr. and Mrs. Richard Robberson, Mr. and Mrs. Arthur Pearson (1942–1963), and Mr. and Mrs. Milton Moon (1963–1989). Both of the Moons grew up in the neighborhood. Mrs. Moon in this very home as the daughter of the Pearsons. The Moons converted the dining room to a den with a fireplace, updated the kitchen, and built a deck on the rear of the home.

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