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In 1066 after the battle of Hastings, King Harold's widow stayed in Winchester but when the Normans arrived she surrendered the town and was allowed to leave in peace. William rebuilt the Royal Palace. The new palace was twice the size of the old Saxon palace. William also built a castle in the west of Winchester. Sixty houses were demolished to make way for it. At first it was made of wood but in the early 12th century it was rebuilt in stone.
After 1079 the Normans demolished the Old Minster Cathedral and built a new cathedral on the site. Early in the 12th century the Nunnaminster (St Marys Abbey) was rebuilt. The New Minster monastery was moved to a new site north of Winchester. It became known as Hyde Abbey. In the Middle Ages the church ran the only 'hospitals'. In 1136 the Hospital of St Cross was built in Winchester. Wolvesey castle, the Bishops residence, was built early in the 12th century.
In the 13th century the friars arrived in Winchester. Friars were like monks except instead of withdrawing from the world they went out into the world to help the poor and the sick and to preach. The Dominican friars (known as black friars because of their black costumes) arrived about 1230 and lived in a building between the Itchen and Busket Street. Franciscan friars (called grey friars) arrived in Winchester about 1230 and lived near Eastgate. Carmelite friars followed them in about 1278. They lived near St. Michael's church. Augustinian friars arrived in Winchester about the same time as the Carmelites and lived near Southgate.
Between 1135 and 1154 there was civil war in England between Stephen and Matilda. In 1141 a battle was fought in Winchester, which became known as the rout of Winchester. The bishop of Winchester fell out with Matilda and his men took refuge in Wolvesey castle. Matilda's army then occupied the town of Winchester and laid siege to the castle. However Stephen's army surrounded Winchester. So there was the strange situation of an army in Wolvesey castle, under siege from an army in the town, under siege from another army outside the walls! Matilda's army eventually decided to fight their way out of Winchester and went out through the town gates. But during the fighting parts of the town were set alight and burned.
More trouble followed in 1264 when there was civil war between the king and his barons led by Simon De Monfort. The people of Winchester supported the king but the monks in the town supported De Monfort. In 1264 they came to blows when the townspeople found out the monks were planning to let De Monfort's men into the town through the Kings gate. The townspeople killed several monks and set fire to the Canon gate. The flames to spread to the Kings gate and its adjoining houses. The next year, 1265, De Monfort's men captured Winchester. They pillaged shops and killed many Jews.
In the 13th century Winchester castle was rebuilt and 'modernised'. The square keep was replaced with a round one. In 1236 panes of glass were installed in the windows. (Glass windows were the height of luxury in those days and few people could afford them).