Very few prehistoric remains have been found in Winslow parish. Neolithic flints and Late Iron Age pottery were found at Magpie Farm in building works; a Lower to Middle Palaeolithic axe fragment was found in a peat bed in the parish and the place-name Dudslow suggests the presence of barrows, possibly of a Bronze Age date, but they could be later. Roman pottery and a leadweight were found in a fieldwalking survey at Shipton Mead Farm, Roman pottery was found in a metal-detecting survey at Shipton Farm and Roman metalwork was found in the eighteenth century on Station Road.
Some early Saxon burials were found in Hayman’s Pit in the nineteenth and twentieth century, possibly associated with a mound and Saxon coins were found on Dene’s Hill in the nineteenth century, but have since been dispersed. There is some evidence that suggests that Red Field was the site of a battle in the early Saxon period and that Winslow was the site of an eighth century palace. The boundary of Winslow manor is recorded in a tenth century document, which mentions a ford over the Claydon Brook and The Street that was the southern border of Granborough. The ditch and bank called Mown Ditch may be part of this tenth century boundary, as could similar earthworks at Tinker’s End.
The medieval period is also not well represented in terms of surviving remains or records. There are records that Shipton was a village in the thirteenth century and there are more modern records of houses with mullion windows that are now just house platforms. Thirteenth to fourteenth century pottery was found in building works at Shipton as well. A medieval ford was recorded in a field visit to Shipton Farm. There are also historical records of a quarry in the parish at some point in the medieval period, though its location is now not known. Twelfth to thirteenth century pottery was found in the garden of 36 Highfield Road and a fragment of medieval quern has been found near Winslow but otherwise very few finds have been reported. A burial was found outside the churchyard gates and probably belonged to a pauper who could not afford to be buried within the churchyard. It may date to the medieval or post-medieval period.
The oldest standing building is St Lawrence church, which dates to the fourteenth century and has a fifteenth century cross in the churchyard. There is a sixteenth century map that records some other structures, like Great Horwood Bridge and Little Horwood bridge, a windmill east of Brook Farm, a watermill near Shipton Farm, a farmstead on the Biggin Estate and a market-place and Market Hall in what is now Market Square. Many of the entries in the Historic Environment Record are of listed buildings. Much of Market Square, Horn Street and the High Street is listed. The listed buildings range from the fifteenth century cruck-built house at 29 Sheep Street to the nineteenth century former workhouse master's house on the High Street. Many of the rest date to the seventeenth century. Some of those of especial interest include the seventeenth century timber-framed houses at 8-10 Horn Street that used to be a bakehouse or the eighteenth to nineteenth century house called Westside that was the servants’ accommodation for Winslow House, which has eighteenth century formal gardens. Keach’s meeting house was a seventeenth century Baptist Chapel with a small graveyard attached. There is a theory that the plans for the Winslow Hall may have been given the once over by Christopher Wren, but this is difficult to prove. A seventeenth century witch bottle was found at 5 Vicarage Road.
The Norden brickworks may have been around from the year 1700 and there was probably a windmill at Mill Knob, as suggested by the place-name. The nineteenth century saw several industrial structures being built around the parish, such as the brick kiln at Tinker’s End which was recorded on a nineteenth century map and was demolished by 1970 or the gas works on the High Street. There was a nineteenth century brickworks at Railway Wharf as well. A sand-pit was recorded on a nineteenth century map near Rands Farm. The Second World War also left a mark on Winslow parish as there are two small concrete structures which acted as approach guides for Little Horwood Airfield. On one occasion a plane missed these guides and crashed into houses on the High Street. The crash, in which many residents and members of the crew lost their lives, is commemorated on plaques in the church.