The following was written by John C. Downing

  WINSTEAD, WINSTED - The English surnames Winstead, and Winsted were originally acquired form once having lived at one or the other of places so named. Two such places are in the East Riding of Yorkshire in the Wapentake of Winstead. The wapentake is a political district similar to our township or parish. It is near the mouth of the river Humber about two miles from the North Sea.

  The ancient course of the Humber is now called Winstead Drain. About two miles north is Winstead Hall, spelled Wilsted in 1610, but probably too recent to have furnished a surname to a former resident.

  The earliest spellings of the Wapentake were Wivestede in 1033, Wifestad, Wiustad, Wifestede and Wisted recorded in the 1083 Doomsday Book, Wiuestud in 1238 Winsted(e) and Wynestede in 1249, and Winestede and Wiuestead in 1347.

  With these early spellings it would appear that the correct spelling would be the personal name Wifa or Wife. This Old English word is the genitive plural of the Old English "wif" (woman). The Old English word "ste(a)d(r)" meant "farm homestead," but in very early times it applied almost entirely to a diary farm. It is a moot question as to which is the older, the Old English "ste(a)d(r)" or the Old Scandinavian "stathr" which is the closest approximate English spelling

  No individuals of the name could be located in the available early dictionaries.

  The 1790 census lists the spelling Winstead in Maryland, North Carolina, and Virginia. The 1800 North Carolina census lists the spelling Winstead and Winsted.
 

The following was edited by Colin Hinson in the UK to correct some of the discrepancies in the above.

To find out more try this link: http://www.genuki.org.uk/big/eng/YKS/ERY/Winestead/

  WINSTEAD, WINSTED - The English surnames Winstead, and Winsted were probably originally acquired from once having lived at what is now the village of Winestead, the "parish town" of the Ancient Parish of Winestead in the Wapentake of Holderness in the East Riding of Yorkshire. A wapentake was an administrative area political district containing 20 or 30 parishes. Winestead is near the mouth of the river Humber just over 3 miles west from the North Sea.

The ancient bank of the Humber used to be roughly where Winstead Drain now runs. Just under a mile north of Winestead village is Winestead Hall, spelled Wilsted in 1610 (by Speed), but probably too recent to have furnished a surname to a former resident.

The earliest spellings of the village name were Winestede and Wisestade in 1033, Wiuestad, Wifestede and Wistede recorded in the 1086 Domesday Book, Wiuestud in 1238, Wynested(e) and Wynestede in 1249, and Winestede and Wiuestead in 1347.

There is some difficulty with the early spellings, and it has been proposed that the correct spelling should be "Wifestead". This gives two options: Wifa or Wife (as a personal name) or Wifa being the genitive plural of Wif (a 'woman'). As the occurences of "stead" with a personal name are virtually non-existent, it is normally assumed that the latter is more likely. The Old English word "ste(a)d(r)" meant "farm homestead," but in very early times it applied almost entirely to a dairy farm. It is a moot question as to which is the older, the Old English "ste(a)d(r)" or the Old Scandinavian "stathr" which is the closest approximate English spelling.
There is a record of a Thomas Weyght de Winstead (note, no "e" after "Win" and a previously unknown spelling) in Poulson's "History of Holderness".

No individuals of the name could be located in the available early dictionaries.

The 1790 census lists the spelling Winstead in Maryland, North Carolina, and Virginia. The 1800 North Carolina census lists the spelling Winstead and Winsted.