Rolling Hills is an entirely gated city with private roads and three guarded gates located at Palos Verdes Drive North (main gate), Palos Verdes Drive East (Eastfield gate) and Crest Road (Crest gate). Rolling Hills extends from Palos Verdes Drive North to the top of the peninsula and over the crest down the South side of the peninsula to the hillside above the Portuguese Bend area; and from the Westfield/Crenshaw Blvd. area to Rancho Palos Verdes on the East. Access to the city is by permit and guests must be authorized to a gate officer, from a resident,  for entrance.

A. E. Hanson, a landscape architect, under arrangement with Frank Vanderlip, became the developer of Rolling Hills, marketing the idea of individual dude ranches. On a trip to Virginia he became enthralled with the architecture of the town of Williamsburg  which was restored by the Rockefellers. He selected a lane in Rolling Hills near the front gate and contracted the well known architect Paul Williams to build 14 homes  of pre-selected Williamsburg colonial styles. He named the street Williamsburg Lane and these homes are there to this day. This is the only area of the city with this homestyle.

The lots in Rolling Hills are generally greater than one acre and include many multi acreage properties. This is an equestrian city with an extensive 23 mile private trail system. Generally, all homes are required to be one level, ranch style, and painted white. Split levels have been accomplished through under grounding techniques. All border fences must be white three rail. There are no street lights or sidewalks in the city and outdoor lighting is limited. Most homes are on septic system since there is no public sewer system within most of the city.

There is a landslide zone called Flying Triangle located on the South side of Rolling Hills above the Portuguese Bend slide. Building is limited in this slide area. Also a small land movement at the entrance of Poppy Trail Road has required the realignment of that roadway.

The city is maintained through the Rolling Hills Community Association (RHCA) which assesses each parcel according to its assessed value (currently about 20 cents per hundred). The RHCA provides the community with two riding rings (Hesse Gap and Poppy Trail); and 3 tennis courts at the main gate location. The county of Los Angeles maintains a fire station on Crest Road in Rolling Hills. Rolling Hills is part of the peninsula school system but does not have any school sites within the gated city. Rancho del Mar continuation high school is located in Rolling Hills but accessed outside of the Crest Road gate.