Although some Roman remains have been found on Wearyall Hill, and in the in-fill used when the Abbey was built and rebuilt, we do not know where the Roman villa or settlement was.
The Tor was certainly fortified and occupied by the sixth century but the development of the main settlement probably followed upon the foundation of the Abbey. The likely nucleus of the early town was round an open space in front of the main Abbey gate. It was certainly still comparatively small by Norman times, the Domesday inquest describing it as a vill with 21 tenants living in serfdom, 33 landless labourers and 17 other families, virtually slaves.
As the town’s population and wealth increased, with the growth of the Abbey in Norman times, a “New Town” was probably planned and built to the east, perhaps in the early twelfth century. It included the Great Street (High Street) and the Church of St John North Binne. The daughter Church of St Benignus (Benedict) was built west of the open space before the New Town developments and both Churches were rebuilt in the 15th century and St Benedict’s again in the 19th century. At the time of the building of the High Street the market place was between it and the Abbey precinct with an extension along Magdalen Street from the Cross to the Pump House.
By the beginning of the 17th century the built up part of the town consisted of the four roads meeting at the Cross; Benedict Street as far as Fairfield Gardens, Northload Street as far as the Manor House (just south of Manor House Road), the west side of Magdalene Street as far as the Chaingate and High Street with its extension, Bove Town and Wells Way. Other houses were in Lambrook Street and Chilkwell Street as far as Chalice Well, the north side of Silver Street, Grope Lane to the south of St Benedict’s Church and in Norbins Lane by St John's Church.
Even as late as the 19th century there was a large number of bartons (farm yards) in each of these roads and very little building outside the mediaeval building limits. The densest housing was in Hanover Square where there were eleven dwellings, including the Rose and Crown stables, all behind the two buildings flanking the entrance to Silver Street opposite St John's Church.
Towards the end of the eighteenth century, as the population reached 2,000, the extra houses needed were often built as terraces at right angles to the road. An early example is Marchant’s Buildings off Northload Street. They filled the plot of one former house or barton with perhaps a dozen new houses. Another terrace from this time was built opposite the Abbey Barn in Bere Lane and more houses filled Hill Head. In the second half of the 19th century, when the population rose from 3,000 to 4,000, the end of the new Street Road was built upon, together with Lambrook Street, Manor House Road, King Street, more terraces off Nortload Street and Victoria Buildings, built on one mediaeval burgage plot between the High Street and Silver Street.
The first new roads for housing were the widened Norbins Road and then George Street, laid out at the end of the 19th century when the market moved there from Magdalene Street. During the Edwardian period a number of larger houses, often semi-detached, were built in Street Road, Ashwell Lane, Coursing Batch and Wells Road whilst part of the fair field was developed on the south side of Station Road (Benedict Street) by John Merrick.