Harewell was to inherit Wootton Wawen only after the death of his mother (who was still living in 1389), and his early connexions were all with Somerset, where his uncle, John, was bishop of Bath and Wells (1366-86).
Yet despite his interests in the West Country Harewell chose to live in Warwickshire, and over the years he added to his property in that county, his most notable acquisitions being the manors of Stourton (1397) and Shottery in Stratford-upon-Avon (by 1402). He and his third wife became members of the guild of Holy Trinity at Coventry.
In the meantime, Harewell had continued to be of service to Joan, the widow of Warwick’s uncle, Lord Beauchamp of Abergavenny. Since 1415 he had acted as a trustee of the Fitzalan estates which she held for life, and he had also undertaken the feoffeeship of lands in Kent which had been settled on her son, Lord Richard. By 1426 he was receiving from Lady Joan separate annuities of £10 and £3 6s.8d., the latter being specifically for his services as her councillor. Joan herself was party to transactions whereby the Warwickshire manors of Bidford and Broom were settled for life on Harewell’s brother, Thomas (another of her retainers), with reversion to John’s heirs. But these were not the only concerns of John Harewell: when, in 1426, he took out royal letters of protection to join the duke of Bedford’s company in France, it was evidently with the intention of settling the affairs there of the late William Venour, his brother-in-law, for whom he was currently acting as executor.
Harewell’s link with the Warwick affinity was the single most important factor in his career, and one which he strengthened through the marriages of his four elder sons. Thus, the eldest, Roger, was married to Agnes, daughter of Sir William Clopton, grand daughter of the Worcestershire lawyer Alexander Besford, niece of Thomas Throckmorton and cousin of John Throckmorton; and John, Richard and William married the three daughters and coheirs of Besford’s daughter, Margaret, and her husband John Dixton of Dixton, Gloucestershire.
