Although 'The Mount' at the end of Beaudesert Lane has no building, it gives the best overall view of the town and is the site of the 12th century 'motte and bailey' castle built by Thurston de Montfort who probably also built, around 1170, St Nicholas church, a fine example of Norman architecture. At the other end of Beaudesert Lane the original church of St John the Baptist was built in 1367 but the present church was constructed about 1448 in the perpendicular style.
The remains of the 15th century Market Cross stand in the old Market Place near the centre of the town on the High Street, which is a classified conservation area and contains many buildings of interest including the Guild Hall, a restored half-timbered Elizabethan building, just north of St John's church. Opposite stands the White Swan Hotel, a 16th century coaching inn. Further north is the Blue Bell Inn, a late 15th century timber framed building. Many private houses on the High Street were 'public houses' in earlier times and many of the brick-faced elevations conceal older timber framed structures. A good example being the Three Tuns Inn, where the timber 'cruck' frame and brick façade can clearly be seen from the south.
Other notable historic buildings in the High Street include Brook House at the north end (previously a school) the Stone House, near the Market Cross (built in the 18th century and formerly an asylum, post office and telephone exchange) and The Yew Trees (originating in the 16th century) towards the south end. Henley-in-Arden also has, within its limits, private houses of more recent design by Charles Voysey and Erno Goldfinger.
Anyone seeking more information on the architecture and history of the town should visit the Heritage Centre at 150 High Street, which is itself a building of historical interest.