From about the middle of the 15th century to the 19th century the prosperity of Painswick depended mainly on the wool trade and the production of super-fine broadcloth. This cloth was made from short-staple wool obtainedfrom the large flocks of sheep kept on the Cotswolds. During the 17th & 18th century, when the wool trade flourished, some farmhouses around Painswick were rebuilt or enlarged. Well Farm dates from 1680 and remains largely un-altered.The mounting block  stands near the house. The farmhouses at Ifold and Spoonbed  were built in the 18th century. Many farm buildings of traditional design still stand. Quarry Barn  is in a field some distance from the farmhouse. The barn at Holcombe Farm dates from about 1710 and is a good example of a typical Cotswold barn.

Before the wool was spun, it was washed and hung in round towers to dry. The 3-storey tower in Kemps Lane was built in the 18th century: it is now used as a workshop. The small 18th century tower by the Painswick Stream at Highgrove has now collapsed completely with no remaining trace. The wool was stored in barns. The room at the rear of Byfield House in Bisley Street  was a wool barn in the 17th and 18th centuryues. The clothier distributed the wool to spinters, women who spun the wool in their cottages, and then passed it to the weavers. Although some mills had weaving rooms, most weavers worked at home. The finishing processes at the mill produced smooth broadcloth.

By the beginning of the 19th century there were nearly 30 cloth mills in Painswick Parish, most of them using water power to drive the mill machinery. Of the buildings that remain Savory's Pin Mill was the last to remain a working mill closing in 1982.
There was a mill here in the 15th century, but the present buildings date from the 18th century. When the local cloth trade declined, the mill became a corn mill and, in 1850, a pin mill. The water wheel was removed from the wheel channel in the 1960s and the sluice gates are no longer used.The 17th century King's Mill, built on the site of a 15th century mill, was a cloth mill until the middle of the 19th century and then a pin mill. The 30-foot long weavers window is one of the longest in Gloucestershire

The prosperity of the clothiers in the 17th and 18th centuries is shown by their fine houses, several of which are still private residences. Painswick Mill House by Painswick Stream, dates from 1634. The mill made cloth until the 19th century when it became a silk mill and then a pin mill. The sluice gates are still used to control the flow of the stream. Upsteam from Painswick Mill is Cap Mill which specialised in making the caps worn by workers in the cloth industry to denote their occupation. The mill house has a weavers mark above the porch with the date 1678 and the initials of the clothier. Washbrook Mill was a corn mill then a cloth mill. A tablet in the wall of the house is dated 1691.

In addition to being a centre of the cloth trade, Painswick was a market town, a charter for a weekly market being granted in 1253. The market was held by the cross, the market hall standing where Throne now stands. Two pillars of the hall are built into an interior wall of Thorne. Close to the market were the cottages in Vicarage Street where weavers and other workers lived. The street was once the slum of Painswick, the cottages have been renovated in recent years. Cottages for mill workers were sometimes built beside the mill, as at Damsells Mill. The mill dates from 1674 . It was a cloth mill until the 1820s, then a flour mill and now a private house. The water wheel still stands inside the building.

During the 17th century not only were many new houses built in and around Painswick, several old properties were restored or enlarged. At Sheephouse, the house once occupied by the Sheep Bailiff was rebuilt and the dovecote added. The south wing was built in the early 18th century. Holcombe house was rebuilt for a clothier in the late 17th century; it was restored and enlarged in the 1920s. The barn used to have a tiled roof. One of the new houses of the 17th century was Wick Street House which stands at the old main road between Painswick and Stroud. It was built for Giles Fletcher, a clothier and Constable of the Manor, whose initials and the date 1633 are carved beside the weavers mark above the front door.

In Bisley Street are some of the oldest buildings in Painswick, some of them dating from the 14th century. This used to be the main street of the town, as it lay on the route between two other important centres of trade, Gloucester and Bisley. New Hall is described in records of 1420 as a Clother-makers Hall. The wool and cloth were carried to and from Painswick by packhorses and donkeys. The door of the Chur and of Byfield House are donkey doors through which the donkeys reached the rear of the buildings. The houses now called Wickstone, Fleece and Litlle Fleece used to be the Fleece Inn which closed in the early part of the 20th century. The arch over the window of Wickstone was the packhorse entrance to the inn courtyard.

Several clothiers built their houses in the centre of Painswick and not next to their mills. Court house was built about 1604 for Thomas Gardner. The house stands on what is thought to have been the site of a former Manor House where the Manor Courts were held. Thomas Gardner sold the house to Dr John Searman, the Diocesan Chancellor who added the south-west wing. The north wing was built in the 1930s. Inside the house there is 17th century panneling; the carved stone urn surmounts a gatepost in the grounds of Dover House which was probably built for a member of the Loveday family of clothiers. The house dates from about 1720 and is considered to be a perfect example of a small Early Georgian Cotswold House.