Alice Chestre was the wife of Bristol draper Henry Chestre who became a successful merchant in her own right after his death.
As the result of Henry's successful trading ventures in Spain, Portugal and France, Alice was a wealthy widow and carried on his business at Cook's Row. From 1473 until her death she traded in cloth, wine and other commodities with Ireland, Spain, Portugal and Flanders, often in her own ships. She was unusual in this respect, as most merchant widows seemed to have traded just long enough to honour their late husband's outstanding contracts.
Exactly why Alice decided to have a new house built is unknown. Bristol's cloth exports had trebled in the late 1400s and so it's possible that her success in business simply meant she could afford to do so. Her contract with Stephen Morgan clearly shows that the new house was in keeping with many others in Bristol at that time. It had a narrow front with living quarters over a ground-floor shop and was built on the same piece of land that had been granted to Henry in 1463. Land prices were relatively high and in the cramped conditions of the medieval town, many people, including Alice, had to live above their work.
When Alice's new house was built, Bristol was full of merchant's houses and warehouses, craftsmen's shops and homes with their gabled roofs leaning to meet one another across dirty, dark and confined streets.