The short answer
The old core is late seventeenth-century: Whitley House, Whitley Farmhouse, Slade's Farmhouse and the Pear Tree Inn, then early eighteenth-century farmhouses. Their roofs have been altered over centuries, so each repair starts by working out what is original.
Whitley is a village in three parts, Upper, Middle and Lower, in the civil parish of Melksham Without. The older houses are scattered through them rather than gathered round a green, which means a roofer meets them one at a time, each with its own yard, garden and outbuildings.
Q1.1What do the older houses ask of a roof?
A house this age needs a covering that sheds water cleanly, a structure strong enough to carry it and details that keep damp out of the walls. Over centuries coverings change. A farmhouse that began in one material may have gained another, and the timbers beneath may not suit the weight now on them. We look from inside as well as out, because the underside of a roof tells you far more than the top of it.
Q1.2Should an old roof be repaired or re-covered?
A sound covering with one local fault is a repair job, and that is gentler on the building and on your budget. Where rot has run across the battens of a whole slope, re-covering makes more sense, sorting the good tiles for reuse and matching new ones among them. Which applies is spelled out to you, with photographs of your own roof as the evidence. A repair that holds for a few winters and then forces a full re-roof would be false economy, so you hear about it where the evidence points that way.
Q1.3Who decides about listed buildings?
Whitley House and the Pear Tree Inn have entries on the National Heritage List, and the grades are worth checking for any house you suspect is affected. Wiltshire Council's planning team decides where consent is needed. Our roof repairs page describes how a fault is worked through before a fix is proposed.
Chimneys on houses like these deserve their own look. A stack that has stood for three hundred years can lean slightly, and the flashings and the flaunching, the sloping mortar crown at the top of the stack, have often been renewed more than once. Each layer of past work gets checked before anything more is added.