One of the oldest structures in the area of Gerrards Cross is a hillfort that dates back to the late Bronze Age. According to studies conducted by the Gerrards Cross Parish Council, it was constructed between 1200 B.C. and 100 B.C. and is an elaborate piece of early English architecture with a number of fortifications. During some of the first scientific excavations, in 1924, pottery was found at the site dating to the early Iron Age.
The area that includes Gerrards Cross was first addressed in writing as a major region of the Anglo-Saxon population in 949 in the Anglo-Saxon Chronicle, an Old English chronicle detailing the history of the culture. At the time, the area was known as Caedele's Spring. In 1237, the villages of the area were separated under feudal boundaries. The future site of Gerrards Cross became part of Chalfont St. Peter, named after the village's church.
According to historian Julian Hunt in "Gerrards Cross: A History," the region became very popular with the wealthy elite of England in the late 1700s. The Old Berkely Hunt club chose Latchmore Pond, a scenic area, to hold meetings in the 1790s. In the 1860s, due to the mass influx of wealthy visitors, the area became known as the "Brighton of Bucks." The important transit site, the Oxford Road, was the main hub for activity, bringing in visitors from all over the country.
In 1906, a major railroad station was opened in Gerrards Cross. Called the Great Western and Great Central Joint Railway, the station stimulated a large influx of new residents to the area, with a number of famous architects among them, including Stanley Hamp and Robert Muir. The architectural firms founded in the area pioneered a number of new design elements specifically geared toward the high class residential market.
One of the most prevalent features of Gerrards Cross is St. James Church. According to the church itself, the original church bearing the name was constructed at least as early as the 13th century in the Alderbourne Valley. In 1610, the church was then transferred to the area of Fulmer, where the building stands to this day. However, the new St. James Church was constructed in 1859 in the shape of a Latin cross, with strong influences from the Byzantine culture.