A long, detailed and thoughtful piece of information. I am adding it to my archives.
In case you don't know Lochwinnoch is a small town on the west bank of Castle Semple Loch (also known as Lochwinnoch) On the easten side there are a number of farm properies that have a long association with the Caldwell name. These properties were inhabited as either tenants or owners (I know not which). The names I have come across are "Lochside" "Belltrees" "Gavin" "Risk" ""Lorabar" "Auchengrange" "Yardfoot" "Barfod" "Park". Caldwell's are found at the township of Beith and further north at Kilbarchan and Paisley where they were most probably weavers.
I stress that there appear to be Caldwell's in some numbers all over various Lowland areas of Scotland and I only mention areas where they appear most concentrated or I have noted specific links.
The Hall of Little Caldwell from ancient maps seems to be the Tower marked on modern ordinance survey maps on the road between Howwood and Lugton on the East Bank of the modern Barcraigs Reservoir.
The Caldwell Tower is just that - a small tower still standing and I have a photogaph of it on a farm just West of Uplawmoor. It is not farm from the current mansion of Caldwell which was the residence of the Mure family. I also have an etching of the tower from the Muir papers published by Maitland Club - it resembles the photograph.
Although the Caldwell Tower bears our name it is a very long time since it has had any connection with our direct family (if ever).
The Hall of Little Caldwell remained in Caldwell hands much longer in the hands of a cadet branch of the family who became the "Gudemen of Caldwell".
My family seem to have been in the Kilmarnock-Ayr region of Ayrshire from ancient times. From at least the mid 1700's they were coalminers. Whether they were descended from romantic landed forebears in reduced circumstances or whether they were always poor folk time and further research will tell.
I do know that the better-off Caldwell ancestors from mid-Ayrshire were connected with the properties of Todriggs (late 1400's) and Annanhill both just outside and to the West of Kilmarnock. There was also a grant of land at "Gaylis" (formerly Scottishaw) on the coast near Dundonald and not far from Troon. This was also in the late 1400's. It is interesting to note that at the time the King of Scotland resided at Dundonald castle and that Scottishaw might be loosely translated as Scot's Wood or perhaps even if the King were "the Scot" even "King's Wood".
Gaylis is modern Gailes on the Ayrshire coast.
There is a romantic story about the grant being the reward for success in a tournament and that Gay Lys or beautiful Lily was the title awarded and betowed upon the property. I note that the Gayley family have been associated with the Caldwell family in Ireland.
As a further note the grant was made a few years after the Battle of Otterburn. Otterburn is regarded as the second most rewarding victory for Scotland after Bannockburn (in ransom money). The ransoms went to the King who in turn parcelled out favours to those who brought in such largess. Polnoon Castle was built by a Montgomery out of the proceeds of his share of the ransom of Percy Hotspur. Perhaps a Caldwell was able to ransom some lesser but still wealthy individual?