A 2+1⁄2 story Georgian home built on large sandstone blocks, the Gregg House has brick exterior walls generally one foot (0.30 m) thick.

A small 1+1⁄2 story building is connected via a breezeway, called an "ice house" by the Gregg family.

After growing up on a Washington County farm, Gregg read law in Fayetteville and passed the bar exam, rising to become a prominent attorney in town.

Gregg also became president of the Bank of Fayetteville and was defeated in a gubernatorial bid by Simon Pollard Hughes, Jr.

Following his death in 1891, courts, businesses, banks, and the university all closed on the day of Gregg's funeral.