In the first decade of the seventeenth century, Sir Hugh Montgomery established Newtownards in the vicinity of a ruined mediaeval Priory Church. He reconstructed the conventual buildings of the old priory as his residence, Newtown House.
At the same time he enclosed the grounds in a square bawn with flanking towers. The north wall ran along what is now the south side of Court Street as far as no. 37, but the south wall still survives alongside a disused canal. Newtown House was burnt down in 1664, but the Ordnance Survey map of 1834 shows the three flankers and bawn wall still in place, together with formal gardens and an orchard in the northern half of the bawn.
In 1744 the town was sold to Alexander Stewart, who was subsequently ennobled as the Marquis of Londonderry, and a Londonderry Estate map dated 1841 shows Court Street with several isolated terraces of houses on the south side, but the site today occupied by nos. 37 and 39 was still empty. These two houses, which occupy part of the site of the seventeenth century orchard, appear for the first time on an estate map of 1848, and unusually they share a central carriageway entrance. A tall random stone wall which separates the back yards of nos.35 and 37 could well be the last surviving remnant of the seventeenth century bawn wall on that side. Court Street takes its name from the fact that the town court convened in the old church from 1817 until the late 1840s. Early street directories and valuation records indicate that the street was inhabited by skilled workers, together with a few corn merchants and weaving agents.
The houses became empty in the mid-1980s by which time they were owned by the N I Housing Executive, which had ear-marked them for demolition. Hearth was able to acquire them and obtain housing association funding for the restoration of the two houses and conversion of the rear stable block into flats. The houses were provided with new kitchen returns and the roof structures were strengthened, but they were otherwise little altered. The stable block required extensive structural work, and some old door and window openings were retained externally but blocked up inside; the old external staircase to the stable now serves as the entrance to the upper flat.