Stepaside village developed in the 18th and early 19th Centuries when the adjacent medieval settlement of Kilgobbin was bypassed by a new stretch of the Enniskerry Road, built from what is now Lamb's Cross through to Kilternan. Stepaside became a new staging post along this route, while Kilgobbin Road with its Coaching Inn (now Oldtown House) was no longer used by goods traffic or stage coaches.
Stepaside is served by several Dublin Bus services. The Luas Green Line has been extended to Cherrywood and the nearest stops (Glencairn or The Gallops) are approx 2 kilometres from the centre of Stepaside.
Since 2002 the Stepaside area has witnessed an extensive homebuilding programme and an accompanying large growth in population. Previously a separate rural village, it has been absorbed by the Dublin conurbation to the north and east. Dún Laoghaire-Rathdown County Council recently announced plans to build a community park for the Carrickmines, Ballyogan, and Stepaside areas at a cost of €40 million. A large civic centre is currently being built and the park will be named after Samuel Beckett.