The Cholderton Estate was assembled in the late 19th century by Henry Charles Stephens as a series of acquisitions designed to create a holding big enough to become a model of Victorian progressive farming. Over a period beginning in 1889 a number of smaller estates and farms were purchased.

At its largest, the Estate covered more than 5,000 acres (2,000ha), and Henry Charles Stephens set about making it as efficient as possible. Meticulous documentation of every acre was a key part of this process, and the majority of these documents survive in the Wiltshire Record Office at Trowbridge. These reveal that a rotation system was a critical ingredient in the striving for high productivity. Stephens was a chemist, and he applied the same careful, scientific approach to farming as he did to his other interests.

It is from this period that the ‘look’ of the present-day Estate largely derives. Stephens laid out woodlands of various types, including a small arboretum, and he either refurbished or had built nearly all of the buildings on the Estate. A good deal of this Victorian landscape character survives, and it is one of the reasons why the Estate was designated a Countryside Heritage Site by Hampshire County Council in 1985, and listed on the Hampshire Register of Historic Parks and Gardens.
Local materials including brick, flint, cob and some timbering were used for most of the Victorian building work.

Photographs of these buildings and groups of buildings when new show them to be handsome, robust and an integral part of the landscape. Cholderton Lodge and Home Farm are both Grade II listed buildings, together with several others.