Caldbeck also got many commissions in Clondalkin due to his local family connections. One example was the neo-gothic Church of the Immaculate Conception and St Killian at Convent Road. He did a great deal of work for the National Bank, founded by Daniel O’Connell in 1834-5 . He catered to the bank’s patriotic leanings by including numerous celtic details in his architectural designs. The National Bank at Ennis is a good example of the “Caldbeck Hybrid”. This was a style best described as being like an “Italian tourist in Irish Romanesque garments".(3.)

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The same might also be said about St Anne’s on “The Hill”, Monkstown, the summer residence that the architect built presumably for his own use in the late 1850s and which he originally simply called The Hill. Again Caldbeck’s account book indicates that he was doing quite a bit of work for domestic clients in the Monkstown area leading up to this time and this is how he may have seen the potential of becoming a developer there. He went on to develop most of the other land lots on “The Hill”, which he purchased in 1858 from local ground landlords, Michael, Earl of Longford and Thomas, Viscount De Vesci.

Caldbeck’s new house overlooked the old twenty-four bed Monkstown Hospital and the well-known local source of well water,  “Juggy’s Well”.  He took an active interest in this well and in 1864 he suggested plans to the Kingstown Commissioners for an Italianate statue to be erected over the well’s entrance, which was rejected.Caldbeck’s own house was built of red brick with a tower topped by cast-iron railings. The popularity of stain-glass windows and heraldry at the time is reflected in the west-facing window, where roundels containing what look like bird figures below a coat or arms is seen. The Caldbecks were not an arms-bearing family and it is difficult to identify who these arms might belong to. The distinctive timber eaves of the house are painted black and white. One notable feature is the appearance of several carved, bearded heads on the exterior walls and there is at least one ornamental panel. The ground rent arranged with Viscount de Vesci was £10 per annum. Caldbeck spent £800 on the building and on the sloping gardens of St Anne’s, dominated by a summer house of matching red brick with an unusual hexagonal roof of patterned slates. (4.)

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St Anne’s was not free standing however. It incorporated a separate house called Woodville. As Peter Pearson points out, the house is “semi-detached but the whole building reads as one”. (5.)Were St. Anne’s and Woodville meant to be all one house originally? Or was there a deception at play? Perhaps so. A deed relating to "The Hill" and dating from 1872 stipulated that if any additional house was erected without consent in future the punitive sum of £50 additional ground rent would be levied.(6.)

In 1866 Caldbeck married Anastasia(or Annabella) Hugo at the RC Parish of St Andrew’s, Dublin.(7.) Hugo was the daughter of a Guernsey-based dentist with Cornish roots, Samuel Hugo, (1803-1855) and his Cork-born wife, Mary F. Walsh. The couple had four children, one of whom,George, died young. After six years of marriage William Caldbeck died suddenly at Harcourt Street on 30th of March, 1872. He is buried at Glasnevin Cemetery, appropriately just a few meters from the large sarcophagus of his grand-uncle, John Philpot Curran, at Curran's Square.(8.) Caldbeck died without leaving a will and it appears that Anastasia Caldbeck sold the lease of St Anne’s to a local builder, Christopher Stapleton, for £450 a year after her husband's death (9.) She continued to occupy the house. In 1877 Anastasia Caldbeck married Charles Borromeo Jennings, a Tipperary-born army surgeon, and she had at least three more children. Her association with St Anne's continued into the 1890s, when she moved to the unusual Netley on South Hill Avenue, Booterstown. She died at the Southampton Hotel, Surrey, in 1928. Anastasia Hugo's “one sentence will” in 1929 and the interpretation of the words "use of all my money" in the document led to legal action among her two-family descendants, which was covered extensively by the newspapers.(10.) 

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Other occupants of St. Anne's included Edwin Lapper, English-born non-practicing doctor and Professor of Chemistry at the Royal College of Surgeons, who lived there in the 1890s. In the late 1920s the house was associated with Arthur Panton Watkinson, who had an interior decoration business on St. Stephen’s Green.