Helena left Jamaica with her parents in 1857 when she was barely 2 years old and grew up in Ireland. After her mother died in 1858, it seems likely that she and her baby sister Augusta were looked after by one or other of her O'Flanagan aunts (her third O'Flanagan aunt had become a nun) until her father remarried in 1862. In this connection, it is interesting to note that her O'Flanagan aunt, Maryanne, came to live with Helena and her parents towards the end of her life and appointed Helena the sole executor of her Will ³

In the late 1860s or early 1870s, the O'Flanagan family settled at Pembroke Dock and, for the next 60 years or so, Helena lived in several houses in the town, first with her parents and, after their death, with her stepmother's younger sister, Charlotte Mary Henry (c. 1843-1913). Helena may have lived on her own, possibly with a servant, after Charlotte died but that has not been confirmed.⁴
  
Nothing has been discovered about Helena's life at Pembroke Dock. Judging by newspaper reports from 1870 to 1900, the "fashionable" social life of the town revolved around events organised by the Army officers of the garrison and the Royal Naval establishment there. There are reports of occasional regimental Balls, regular cricket matches in the summer and hunting and steeplechasing in the winter. Given her father's Army connections, there should have been no lack of opportunities for Helena to meet young officers, but if she did, those encounters never led to marriage.

It seems likely that Helena was the beneficiary of her father's and Charlotte's Wills (Charlotte is known to have had property in Dublin) as well as her aunt Maryanne's so probably, she had sufficient income to support herself in a modest manner (the cost of living would not have been high in Pembroke Dock) in her later years. Certainly, in the 1901 and 1911 censuses she is described as living on her own means. When she died in 1930, she left c. £700, possibly to a Roman Catholic cause as she appointed her parish priest* as her Executor. ⁵
  
It is interesting that despite her natural family focus being on her O'Flanagan and Henry connections, Helena was able in later life to produce quite detailed, if sometimes inaccurate, gossipy notes about most of those descended from her Bancroft grandparents.⁶ It shows that, at least by time she was in her 60s, she was in contact with several relations on her mother's side of the family.