Middlebie was the property of the Carruthers family in the 14th century and was later owned by the Maxwells.

In 1202 Pope Innocent III wrote to the priors of St. Oswald’s, Nostell and St. John’s, Pontefract, and Roger, rural dean of Ledsham regarding land at Eglefechan. In his letter he stated that W. de Midleton’s (possibly Middlebie) father had placed certain land of Ecclefechan in gage to Ivo de Crossebi in return for a certain sum of money. Ivo, when alive, and later his son, R. (probably Robert de Crossebi), had received a repayment of the loan but refused to return the land. The land in question seem to have been that of Oulcottis or Woolcotes which was located close to the present farm of Orchard.

In 1351 William Carruthers of Mosswald received a charter of the lands of Middlebie from David II.

William Irving of Kirkconnel was in possession of the lands of Woolcotes, Middlebie and other lands in Hoddom parish by the mid-16th century, receiving a sasine of them in 1551.

Middelby is marked as a tower on Blaeu’s mid-17th map as a tower to the west of Middleby Kirk.

The lands consisting of “The Ten merkland pertaining to Kirkconnell, The half merkland of the half merkland of Blackwoods in Middlebie included” were valued at 400 merks in the valuation rolls of 1671.

I have placed the site of the tower at the farm of Middlebiehill pending further research.