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Lilesville's beginnings date back to the early nineteenth century as settlers moved into the Pee Dee River region of what would become Anson County. Before European settlement, the area was inhabited by Native American tribes who utilized the river system for transportation, fishing, and hunting. As farming families established homesteads, the community began to take shape around agricultural land and river access. The town was later named after local landowners and gradually developed into a small but stable rural settlement serving the surrounding countryside.

Agriculture formed the backbone of Lilesville's early economy, with crops such as cotton, corn, and tobacco playing central roles. The town's location near the Pee Dee River supported trade and the movement of goods, connecting local farmers to regional markets. In the late nineteenth century, the arrival of the railroad significantly boosted economic activity, making Lilesville an important shipping point for agricultural products. Small businesses, warehouses, and service establishments grew around the rail line, reinforcing the town's role as a commercial center for nearby farms.

Transportation and infrastructure improvements continued to influence Lilesville's development over time. The railroad remained a key economic driver for decades, while road improvements in the twentieth century enhanced access to surrounding communities such as Wadesboro and Polkton. Highways connecting Anson County to larger urban areas allowed residents to commute for work and services, while still maintaining the town's rural character. These infrastructure investments supported gradual growth without dramatically altering Lilesville's small-town identity.

Community life in Lilesville has long been centered on family, faith, and local institutions. Churches and schools have served as important gathering places, fostering strong social bonds and shared traditions. The town's population has remained modest, encouraging a sense of familiarity and neighborly support among residents. Community events, agricultural traditions, and civic involvement have helped preserve Lilesville's heritage while adapting to changing economic and social conditions.

Today, Lilesville offers a quiet, rural lifestyle that appeals to homeowners seeking space, affordability, and a close-knit community. Residential properties include historic homes, farmhouses, and newer single-family residences. Its location within Anson County provides convenient access to regional amenities while preserving a slower pace of life. With its agricultural roots, river proximity, and enduring community values, Lilesville remains a welcoming place to live in south-central North Carolina.