8A Ancaster Square

8A Ancaster Square consists of two adjoining single-storey cottages, each with a three-bay rectangular plan, likely dating from the late 18th century. These cottages are located at the rear of Ancaster Square, parallel to the eastern range of the northern side. They are the last two buildings in a row that extends from the back of 59/61 Main Street, which is currently unlisted. Historically, Callander featured similar dwellings behind the Main Street, although most have been altered or raised to two-storeys. As such, these cottages are notable examples of traditional local architecture and are listed at Category C(S) for their significance.

The cottages are symmetrically arranged on their western elevation, with a central door and windows positioned close to the eaves. Notably, 4A has a large modern porch. The eastern elevation faces a car park, where 8A has a large inserted window in the center, while 4A maintains its original window configuration in the outer bays. The outer gable of 8A is steeply pitched and blank.

In terms of materials, the cottages are constructed from random rubble 'pudding stone' with smeared pointing. 8A features a timber two-leaf door, while 4A has a modern timber and glazed porch. Both cottages have pitched grey slate roofs with various rooflights; 8A retains its original bi-partite cast iron chimney. The gable apex stack of 8A has been replaced with a modern gas flue, and there is a slim brick ridge stack at the center topped with a decorative can. The chimney at 4A is a coped random rubble stack raised with brick and has a tapered clay can. Additionally, there are cast iron rainwater goods.