The area around Winchester has been inhabited since
prehistoric times, with three
St. Catherine's Hill, and Worthy Down all in the nearby vicinity. In the
Late Iron Age, a more urban settlement type developed, known as an
oppidum, although the archaeology of this phase remains obscure. It was overrun by the confederation of
tribes known as the
Belgae sometime during the first century BCE. It seems to have been known as Wentā or Venta, from the
Brittonic for "town" or "meeting place".
Roman conquest of Britain, the settlement served as the capital (
Latin: civitas) of the Belgae and was distinguished as Venta Belgarum, "Venta of the Belgae". Although in the early years of the Roman province it was of subsidiary importance to
Chichester, Venta eclipsed them both by the latter half of the second century.
 At the beginning of the third century, Winchester was given protective stone walls.
 At around this time the city covered an area of 144 acres (58 ha), making it among the largest towns in Roman Britain by surface area.
 There was a limited suburban area outside the walls.
 Like many other Roman towns however, Winchester began to decline in the later fourth century.
Roman withdrawal from Britain in 410, urban life seems to have continued at Venta Belgarum until around 450 AD, and a small administrative centre might have continued after that on the site of the later Anglo-Saxon palace.
Ford identifies the community as the Cair Guinntguic
Fort Venta") listed by
Nennius among the 28 cities of
Britain in his
History of the Britons.
 Amid the
Saxon invasions of Britain, cemeteries dating to the 6th and 7th centuries suggest a revival of settlement.
The city became known as Wintan-ceastre ("Fort Venta") in
 In 648,
King Cenwalh of
Wessex erected the Church of SS Peter and Paul, later known as the
Old Minster. This became a cathedral in the 660s when the West Saxon bishopric was transferred from
Dorchester-on-Thames. The present form of the city dates to reconstruction in the late 9th century, when king
Alfred the Great obliterated the Roman street plan in favour of a new grid in order to provide better defence against the
Vikings. The city's first mint appears to date from this period.
In the early tenth century there were two new ecclesiastical establishments, the convent of
Nunnaminster, founded by Alfred's widow
 and the
New Minster. Bishop
Æthelwold of Winchester was a leading figure in the monastic reform movement of the later tenth century. He expelled the secular canons of both minsters and replaced them with monks. He created the drainage system, the 'Lockburn', which served as the town drain until 1875, and still survives. Also in the late tenth century, the Old Minster was enlarged as a centre of the cult of the ninth century
Bishop of Winchester, Saint
Swithun. The three minsters were the home of what architectural historian John Crook describes as "the supreme artistic achievements" of the Winchester School.
The consensus among historians of Anglo-Saxon England is that the court was mobile in this period and there was no fixed capital,
 but Winchester is described by the historian Catherine Cubitt as "the premier city of the West Saxon kingdom."
There was a fire in the city in 1141 during the
Rout of Winchester.
William of Wykeham played a role in the city's restoration. As
Bishop of Winchester he was responsible for much of the current structure of the cathedral, and he founded the still extant public school
Winchester College. During the
Middle Ages, the city was an important centre of the wool trade, before going into a slow decline. The
curfew bell in the bell tower (near the clock in the picture), still sounds at 8:00 pm each evening.
Winchester High Street in the mid 19th century.
The City Cross (also known as the
Buttercross) has been dated to the 15th century, and features 12 statues of the
Virgin Mary, saints and various historical figures. Several statues appear to have been added throughout the structure's history. In 1770,
Thomas Dummer purchased the Buttercross from the Corporation of Winchester, intending to have it re-erected at
Cranbury Park, near
Otterbourne. When his workmen arrived to dismantle the cross, they were prevented from doing so by the people of the city, who "organised a small riot"
 and they were forced to abandon their task. The agreement with the city was cancelled and Dummer erected a
lath and plaster facsimile, which stood in the park for about sixty years before it was destroyed by the weather.
 The Buttercross itself was restored by G. G. Scott in 1865, and still stands in the High Street. It is now a
Scheduled Ancient Monument.
Three notable bronze sculptures can be seen in or from the High Street by major sculptors of the 19th and 20th Centuries, the earliest a monumental statue of
Queen Victoria, now in the
Great Hall, by
Sir Alfred Gilbert (also known as the sculptor of '
Eros' in London's Piccadilly Circus),
King Alfred, facing the city with raised sword from the centre of The Broadway, by
Hamo Thornycroft and the modern striking
Horse and Rider by
Dame Elizabeth Frink at the entrance to the Law Courts.
Jane Austen died in Winchester on 18 July 1817 and is buried in the cathedral.
 While staying in Winchester from mid-August to October 1819, the Romantic poet
John Keats wrote "Isabella", "St. Agnes' Eve", "
To Autumn", "Lamia" and parts of "Hyperion" and the five-act poetic tragedy "Otho The Great".
In 2013, businesses involved in the housing market were reported by a local paper as saying the city's architectural and historical interest, and its fast links to other towns and cities have led Winchester to become one of the most expensive and desirable areas of the country and ranked Winchester as one of the least deprived areas in England and Wales.