The modern development grew around Castlemilk House, a stately old mansion built around Cassilton Tower, which was started in 1460 on the site of a 13th-century castle, and was demolished in 1972.

However, despite the social problems associated with poverty and unemployment, the area has seen the benefits of a regeneration strategy implemented in the 1980s which has focused on improved housing and the development of local arts.

According to Mrs Herbert (Author of the History of Carmunnock), 'The villagers, joyfully taking the opportunity, forcibly threw the unpopular Rev Mr Boyd out of the manse'.

Two trial trenches to the west of the tower discovered a defensive ditch which had been filled with midden material such as pottery, bone, bottle glass and a clay pipe bowl that would date the deposit to the 18th century if not earlier.

[1][8] In 1947, a delegation from Glasgow visited Marseille to see the new social housing designed by the Swiss-French architect Le Corbusier, who was a pioneer of modern urban planning.

However, the city fathers were anxious to ensure that most people remained living within the Glasgow boundaries so they keenly pursued the townships project even with limited space available on which to build.

[1][10] In early 1953, more detailed plans for the development of Castlemilk were prepared by Archibald George Jury, who had been appointed as Glasgow’s first City Architect in 1951, a post he held until his retirement in 1972.

[12] Many of the street names (Ardencraig, Ardmaleish, Birgidale, Dougrie, Dunagoil, Machrie) were derived from rural locations in the County of Bute.

Archibald Jury was the architect responsible for the creation of the three 20-storey tower blocks in Dougrie Road, from the planning stage in 1960 to their completion in 1966 (these are still standing).

[1][13] The Mitchelhill high-rise blocks at Ardencraig Road, built on high and exposed ground at the edge of the Cathkin Braes and designed to be a prominent feature of the city skyline, were designed and built by George Wimpey Ltd, between 1963 and 1965 (they were demolished in 2005);[1][7] Wimpey was also responsible for the construction of Bogany Flats in 1966 (demolished as early as 1993).

After the shopping centre's small Co-op Food supermarket confirmed it would closed its doors in 2016, residents launched a campaign for improved grocery shopping provision in the district, with local bodies failing to attract any suitable tenants for either the Braes Centre (described by campaigners as badly outdated) or at any new standalone sites.

The accompanying stables block (built 1794, designed by David Hamilton and Category B listed) survived and was restored; it now contains the local housing offices, community facilities and a nursery.

Falling population numbers led to Glenwood closing its doors in 1990 (a business centre now occupies the site) and the pupils transferring to Grange, which was renamed Castlemilk High School.

[29] In 2001 that school was rebuilt on a smaller scale on the same site, with the playground and buildings swapping places; St Margaret Mary's was reconstructed in 2002 using the same method.

As part of the regeneration of Castlemilk in 1999, several public artworks were commissioned and placed at prominent entrances into the area; these included works by sculptors Kenny Hunter and Rick Kirby.