Mr Massingham left the firm in July last year after just 12 months in the post and was replaced by then finance director Paul Wallwork.
He spent five years at Gleeson joining as managing director of its house building division and then overseeing a restructuring of the group which saw it sell its building and engineering operations. His career has also seen stints at rival house builders Crest Nicholson, Bryant and Alfred McAlpine.
Mr Massingham said: "With the current uncertainty in the housing market the next year will be a challenge, but it’s one that I am looking forward to embracing.”
Charles Church has also appointed Louise Frampton as sales director and moves across from Taylor Wimpey-owned Bryant.
And Andy Major joins as construction director at the company, which is based in Reigate, Surrey, and also carries out work in Sussex and Kent. Mr Major has previously worked for Crest Homes and Antler Homes.