Between 1870 and 1910 investors purchased farmsteads in Ole Asheboro and began subdividing them for neighborhood housing. In 1902, as the Ole Asheboro neighborhood was one of the most prestigious neighborhoods in the city, trolly service was introduced to "South Greensboro" along Asheboro Street.
Ole Asheboro was home to many important citizens responsible for Greensboro's early growth. Many of the city's most respected judges, merchants, politicians, and entrepreneurs lived in the neighborhood. The result was a remarkable collection of high-style residential architecture and civic buildings. Later in the century this tradition continued as grand single-family houses of varying styles defined Asheboro Street. Behind Asheboro Street, a mix of well-built, middle-class and upper-middle-class homes were constructed. The neighborhood grew up as a prestigious, yet economically diverse community.
In the first decade of the 21st century, the Ole Asheboro neighborhood became a redevelopment area project of Greensboro's Redevelopment Committee.
Source: Ole Asheboro Redevelopment Plan, 2004, www.greensboro-nc.gov, accessed December, 2009.