The windmill is one of Warwickshire's most famous landmarks, standing on a hilltop overlooking the village of Chesterton for nearly 350 years, near by the Roman Fosse Way and about five miles (8 km) south-east of Warwick. It was built in 1632-1633, probably by Sir Edward Peyto, who was Lord of the Chesterton Manor House. At this time John Stone, a pupil of Inigo Jones, was in Chesterton, designing the new Manor House, and he probably helped with the Windmill as well. Sir Edward was a mathematician and astrologer and probably his own architect to the windmill, but although claims have been made that the tower was originally built as an observatory, the estate accounts now at Warwick Record Office show that it has always been a windmill, making it the earliest tower mill in England to retain any of its working parts.
It is built of hard local limestone, with sandstone detailing. The mill tower, unique worldwide in structure and mechanics, is supported on six semicircular arches, on piers, the outer faces of which are arcs of circles radiating from a common centre. A sandstone string course surmounts the six arches and runs round the Tower, below the windows. There are four windows in the tower, two small and two much larger with stone mullioned windows. A small window set in the roof on the opposite side to the sails, has a small plaque above it with the letters "E. P. 1632".
Beside the open ground floor within the arches there are two more floors to the mill, the first, lower, or stone floor 15-foot (4.6 m) above ground level, housing millstones, great spur wheel, hurst frame, sack hoist rope passing through the floor trap, and the upper, second, or hoist floor with brake wheel, main gearing (wallover), sack hoist pulley, and parts of the winding winch. The windshaft and the main parts of the winding system including the wind direction inidicator is installed within the cap. The space inside the arches, until 1930, used to have a wooden structure to store the grain, and an open timber staircase to reach the milling floors. This structure was removed to prevent vandalism. The cap of the mill is a shallow dome which used to be covered with lead sheet, but also because of vandalism is now covered with aluminium. Between the cap and the top of the wall is a system of rollers running in a track plate allowing the cap to be rotated easily. There is a wind direction inidicator on the roof which is continued into the interior, and a small repeat indicator at its lower end, so that the miller could set the mill without leaving his work. The lattice-type-sails are 60 feet (18 m) span counter clock-wise rotation (seen from outside the mill; most of all windmills worldwide rotate clockwise seen from inside the mill - from "under the wind") and with 450 sq ft (42 m²) of canvas. The arched tower covers a very small diameter of 22 feet 9 inches (6.9 m) and it has an unusual "in cap" winding gear for an English windmill, the cap being winded by a hand operated winch having spur and worm gears.
The mill without its sailsIt seems the mill has undergone three major reconstructions, one in 1776 when the mill shaft was modified, and the date carved in the tail of the shaft, and one in 1860 when the old curb and cap framing was altered. By 1910 it had ceased to function as a mill because the winding gear failed to operate, so that her last miller, William Haynes, was no longer able to turn the mill's cap round to make the sails face the wind. He abandoned the mill and moved to another mill nearby. It was not until 1969 that reconstruction of Chesterton Mill began again. The windmill repairs were finished in 1971, and the mill reopened for a few days to the public each year (volunteers from nearby villages help run the open days and provide stewards for the event).
In 1975 it was awarded one of the Civic Trust Heritage Awards, and the mill's status is reflected in the name of the nearby Leamington Football Club ground the New Windmill.
A stone tower similar to Chesterton Windmill exists in Newport, RI, U.S.A. The commonly accepted theory is that it was built by Benedict Arnold around 1676 after a previous wooden mill was blown down in 1675. It is not quite the same as Chesterton Windmill, having eight round pillars, but it was very similar. The Arnold family, whose place of origin is disputed but may have been either Leamington  or further down the Fosse Way, near Ilchester in Somerset, emigrated to Rhode Island in 1635 where Benedict became governor in 1663. This has led to speculation that the Newport Tower was based on Chesterton Windmill. However, some historians, as well as amateur researchers, dispute this theory and have claimed that it is several centuries older, thus being evidence of a pre-Columbian (Viking) settlement in New England.
The 2006 sail accident
In 2006 one of the sails fell off the windmill during an open day, injuring one visitor. Initially, following the incident, the area was roped off to prevent visitors approaching the windmill. The sails themselves were then removed for strengthening. They were finally replaced in late 2007.