In the 1837 Rate Book there were only three cottages recorded. The present Number 8 was converted to a dwelling soon after the Second World War from a stable and coach house which had been built on to the next house in 1860 which at that time was rented by a wheelwright, Thomas Brough. In the first quarter of the nineteenth century, the other two cottages had been beer houses at different times. From 1851 the one on the comer became a butchers shop, run by John Reeves..
The Old Post Office was originally the coach house to the rectory (next door) and it was converted into the house that it is today by 1819. A large (infilled) archway at the back and a wide doorway at the far end of the house are some of the reminders of its origin. The red post box (now disused) was installed in the late 19th century. The small room in the house, directly behind the post box, was used as the Post Office from 1913 to 1993.
The replacement stables for the rectory, a few yards back from the house, and the rectory orchard, were cleared to build the new rectory on the corner of Church Lane in the mid-1980s.
Directly opposite the Old Post Office is Church View Cottage which is a listed building originally constructed in the late 18th century.
The Old Rectory was built in the late eighteenth century and at the time of his death in 1839 it belonged to the Rector of Checkley, the third Reverend Samuel Langley. However he was not living there at that time and the building was inhabited by his tenant, Joseph Walker. Instead the Reverend Langley had resided at Rectory Farm.
It was not until 1843 that it became the Rectory when the Reverend William Hutchinson, Rector since 1839, moved from Rectory Farm. It then remained the Rectory until 1985 when a new vicarage was built on the corner of Church Lane and the main road. The Old Rectory was initially converted into an old peoples residential home but in 2005 was further converted into 11 self contained apartments.
The new vicarage which had been erected in 1985 was sold in 2008 and became a private residence. Since then there has not been a vicarage in Checkley.
This property stands on Church Lane opposite to the church tower. Until the 1840s it was the White Horse Inn standing where there had almost certainly been a hostelry since medieval times. The premises also included a blacksmith's run by William Beardmore of a well-known family of blacksmiths in the Tean area. Originally the back part of the building was let as a separate dwelling. It is now a private house.