27, 29 High Street, Pittenweem

27 and 29 High Street in Pittenweem is a former merchant's house dated 1635, which was re-faced in the late 19th century and features an early 20th-century shopfront. This prominent building has a crowstepped design and consists of two to three storeys with an attic, arranged in a T-plan and part of an irregular terrace that includes a separately listed late 16th-century town house of the Earls of Kellie. At the rear, there is a single-storey and attic projection made of red sandstone with a pantiled roof. The exterior is finished with painted lined render, a painted base course, and a deep band course above the ground floor.

On the south elevation facing High Street, the central door has chamfered edges. To the right, there is a bipartite window with a banded surround. The first and second floors feature moulded architraved windows, all with advanced cills. The broad centre door has six panels and is situated below a large window that has been converted to a bipartite style, with a modern fascia to the right and a well-detailed shop to the left. The first floor has regularly-fenestrated bays, with a bipartite window at the outer left and a moulded date panel at the centre, which is above a modern plaque that reads 'THE OLD MANSE'. The second floor has smaller windows that sit just below the eaves. The rear elevation has a tall, two-bay gable at the centre, with a lower red sandstone projection extending to the right into higher ground.

The shopfront features a geometric-tiled lobby and a decoratively-etched part-glazed door on the left, with a display window on the right above a deep stallriser. This is topped by a multi-pane clerestorey that includes coloured vertical lights and three panels, with the centre panel reading 'TEAS'. There is a blind box with outer handles and a centre locking strip below the modern fascia.

The building has replacement timber sash and case windows with 9- and 12-pane glazing patterns. The roof is covered with grey slates and red clay pantiles, and there are ashlar stacks, one of which is truncated and has a thackstane.

Inside, some good interior details have been retained, including moulded cornices, architraves, panelled timber doors and shutters, and timber fire surrounds with cast iron grates. The hall floor features encaustic tiles, and there is a dog-leg staircase with a boarded timber dado. The shop retains part-glazed timber panelling, a counter, and shelves.