Bedfordshire Historical Record Society published a volume of miscellaneous pieces in 1931 (Volume XIV), one of which was a survey of Bedfordshire windmills by J. Steele Elliott. He noted that a final concord of 1610 between William Towse, esquire and Thomas Trist on the one part and Sir Thomas Dacres mentioned a windmill as part of the Manor of Overdene. The windmill is shown on a map of Bedfordshire by Thomas Jefferys from 1765 [R1/107], it stands in the same place as the surviving mill does today, on the Shelton Road.

Today’s mill was built about 1850 for William N. Bliss. It stands in a field known as Mill Field, suggesting that a windmill may have stood on or near this spot for a very long time – windmills were introduced into England in the last quarter of the 12th century.

J. Steele Elliott wrote of the field on the other side of the road to the mill  and called Mill Close, part of a larger field called Mill Hill: “There is a pond near the centre of this field, which was shown in early maps as of a horse-shoe shape, and might have had some association with a mill site. During personal investigation I made here I came across several blocks of worked limestone near this pond, which had evidently been used formerly in some building”. The Bedfordshire Historic Environment Record [HER] contains information on the county’s historic buildings and landscapes and summaries of each entry can now be found online as part of the Heritage Gateway website. An entry for Mill Field [HER 8137] refers to Steel Elliott’s findings and notes: “Site visit c.1977; eastern half of pond still holds water, western half in dry shallow depression”. It seems likely, then, that either there was another windmill on the other side of Shelton Road, opposite the current mill, or, perhaps more likely, an earlier mill stood on that side of the road and the site moved to the current site at an unknown date.

It is recorded on Benjamin Bradshaw’s tomb-stone in Dean Churchyard that he was born in 1811 at Upper Dean Mill. He was miller at Lower Dean in 1848 and from this evidence we can infer that his father was the tenant miller at Upper Dean in 1811.

The windmill stopped working in 1906. The brick built tower with a rounded crown stands 46 feet high and has a diameter of 18 feet at the base, the walls being 18 inches thick. In 1931 it still carried "parts of two of its shutter sails, and the semblance of a tail-fan. The wooden brake-wheel is 7 feet 6 inches, the crown-wheel is of iron. There were three upper floors, and it ran two pairs of stones. The names of W. Eaton, 1857, J. E. Mehew and William Hall are recorded on the milling-floor; Thomas Eaton was there in 1869; millers of the latter two surnames saw the last of the mill’s days of usefulness, Charles Hall being miller there until 1906. It serves now only for a shelter for cattle. Upper Dean is the property of Mrs. E. L. Wade, of Dean Grange, whose father, J. W. Rawson Ackroyd, purchased it from the original owner and others interested in 1875”.

Bedfordshire and Luton Archives and Records Service has a number of directories for the county dating from 1839 to 1940. These give some details of names and addresses of prominent people in each parish. The following list has been compiled for millers in Upper Dean. County directories were only published every few years and so the dates in the list simply include the first and last reference to a particular individual residing at a property.

• 1864: John Peck;
• 1871: Jonathan Bettles;
• 1877: Thomas Mehew;
• 1885-1903: Charles Hall, and beer retailer;