State Route 258 (SR 258) is a 14.1-mile-long (22.7 km) north–south secondary highway that traverses portions of Robertson and Sumner counties in Middle Tennessee.

SR 258 begins in Sumner County in downtown Hendersonville at a junction with U.S. Route 31E (US 31E).

It traverses and interchange with Vietnam Veterans Boulevard (SR 386, Exit 6) on the north side of town.

It road bisects SR 174 (Long Hollow Pike) at Shackle Island.

About 8.3 miles (13.4 km) later, it arrives at a junction with US 31W, which also marks the Robertson–Sumner county line, at White House.