The Dragon appears to have sixteenth century origins, but was refronted and altered in the late eighteenth or early nineteenth and then clad in mock timber-framing in the later nineteenth century (before 1893). The present four-bay facade is basically late Georgian as old photographs show a two-storey four-bay stuccoed front with deep-eaved roof, hipped at the corner, basically as now, but without the gable and dormers. It was the principal coaching inn, owned by the Powis estate, first recorded in 1770, and as the Green Dragon by John Byng in his tour of 1784. It was called the Dragon in an 1858-9 directory but the Green Dragon in one of 1880.

The interior retains a fireplace in the north-eastern room and moulded beams in the north-western room of sixteenth date. These are of a quality not found elsewhere in the town, and as they are to each side of the carriageway to the rear yard they suggest a sixteenth century building on a remarkably large scale. Recorded landlords include Richard Jones 1770-4, Thomas Clout 1774-90, William Read c1811, Edward Read 1822-50, Thomas Davies c1858-9, Martha Wood 1868-74, Edward Watkin 1878-93, G.J. Clipston 1895-1907, and C.P. Davies 1912-41. Sold by the Powis estate in 1975.
Source: Welton, A, and Welton, J. 2003. The Story of Montgomery: Logaston Press: 50, 107-8, 142-143, 174
RCAHMW, 2 January 2008.