The pattern of development is one of small towns and villages. The eastern parts of the Shire are bounded by the Illawarra escarpment and Morton National Park, with some remnant rainforest and heathland. The north of the Shire is characterised by rugged eucalypt bushland, with gullies, gorges and sandy soils. This area forms part of the catchment for Sydney's water supply and two major storage dams (Avon and Nepean Dams) are in this area. The dams cannot be accessed by any roads within the Wingecarribee Shire but by roads leading off south-east of the Wollondilly Shire. The Wollondilly and Wingecarribee Rivers flow through the west of the Shire, through deep sandstone valleys and much of this area forms part of the catchment for Warragamba Dam. The south of the Shire is bounded by Uringalla Creek and is a sandstone plateaux dissected by deep gorges.
