Walter I’Espec was the first nobleman to build a castle at Helmsley c.1120.
It was probably a timber construction.
It wasn’t until Walter’s death in 1154 that the property passed to his brother-in-law, Peter de Roos in whose family the castle remained until the 17th century.
In 1186 Robert de Roos, Peter’s son, rebuilt and extended the castle in stone. He had constructed, the two main towers, the round towers and main gateway on the south side.
On Robert’s death in 1227, his oldest son William inherited and continued to strengthen the castle. He added another storey to the east tower altered the south barbican and added a new hall that abutted the west tower.
No further alterations were made until the 1560’s when the west tower and hall were
converted into a Tudor styled house
During the Civil War Sir Jordan Crosland and his Royalist garrison underwent a three month siege until they surrendered to Sir Thomas Fairfax. Parliamentary forces then slighted the castle, blowing up the east tower, curtain walls and fortified gates.
The property is now in the care of English Heritage.
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