Prittlewell is included in this study partly because the modest number of landless messuage transactions noted there by Britnell – the earliest in 1323 – may be suggestive of the establishment of a burghal component within a market settlement. Situated in south-east Essex near the shore of the Thames Estuary, towards the top of the south slope of a shallow valley formed by the Prittle Brook, which flows out of the Rayleigh Hills and attracted settlement in prehistoric and Roman periods, Prittlewell is now a conservation area within the borough of Southend-on-Sea. But that borough represents a nineteenth-century development (originally a medieval fishing hamlet) at the southern end of the mother parish of Prittlewell, focused around St. Mary's church. The village – once the principal settlement of the area, at the junction of roads from east, west and north – was absorbed into the expanding town of Southend. St. Mary's embodies Anglo-Saxon remains, though the current church fabric is mainly twelfth century and later. There seem to have been discrete churches on the site in the seventh and tenth centuries, the older possibly associated with warrior or high-status burials (male and female) that yielded weaponry, jewellery, and imported goods, suggesting a social elite with commercial ties to Kent and the continent.

The Domesday record for 1086 shows two manors, Prittlewell and Milton – linked by the north-south road – with St. Mary's the only church in the locality and therefore indicative of Prittlewell's predominance; the village had a moderately large population and large flocks of sheep and goats are documented. Prittlewell was then held by Suein of Essex. Robert Fitz-Suein founded a priory there ca.1110, on a site north-east of the village, as a cell of the Cluniac priory at Lewes, and endowed it with lands from the manor and with the church, the latter undergoing expansion to make it more suitable for the monks. The monastic community was not large but was relatively wealthy in its endowments and must have provided an important consumer for the local market, although caught up in financial maladministration and disputes with the mother-house during the reigns of Henry III and Edward II. The manor itself was divided, with part belonging to the priors and part the Earls of Oxford. Given the possibility of a seventh-century trading community, it is interesting that the name Polsted-wic was traditionally associated with the earls' manor, though this may not signify anything beyond an isolated farmstead.

It was earl Hugh de Vere who obtained in 1238 licence for a Monday market at Prittlewell, and possibly a fair – damage to the Charter Roll entry making this less certain – although not until 1248 that this was challenged by the countess of Kent, widow of Hubert de Burgh, as detrimental to her market at Rayleigh. It was presumably in response to this challenge that Hugh's new licence in 1257, as the countess was declining in health, altered market-day to Fridays; this second licence confirms the existence of a fair around the festival of the Nativity of St. Mary, thus associating it with parish church or priory. There may have been a residual problem, however, for in 1278/79 an inquisition ad quod damnum was necessary before the way was clear for Hugh's son, Robert de Vere, to hand over Prittlewell's market to his daughter Joan, perhaps as part of a marriage settlement.

The market is likely to have been held in a widened stretch of the east-west road, at the T-junction by the church. An extant structure opposite the church was once the wing of a mid-fifteenth century house incorporating a ground-floor shop and upper level high-status hall, while a second building nearby also incorporated a shop. A socio-religious gild was established at similarly late date – probably a few years prior to receiving (1477) royal licence and grant of corporate status – with its own hall and a chapel in the church, indicative of money invested in charitable works. Local prosperity was sufficient to support renovation and expansion of the church in the fifteenth century and domestic rebuilding around the same period. However, the Dissolution removed the priory as a local consumer and Prittlewell's commerce may have transferred to Rochford's market in the sixteenth century, a period in which little residential expansion or church maintenance is documented at Prittlewell. Property boundaries have been sufficiently altered over intervening centuries that it cannot now be said with confidence if any series of burgage plots was laid out at any point; but such would have been consistent with de Vere practice elsewhere.

The foundations of Prittlewell's commerce are little evidenced. We cannot doubt that local agricultural produce, including wool, formed a large part – in 1339 two Prittlewell men were accused of using their houses to help smuggle wool by night down the Thames to parts overseas – while fish and shellfish from the Thames are also likely to have been regular market commodities. Surname evidence suggests that the coastal trade in coal may also have played a role. The estuary attracted some sea-faring vessels, perhaps particularly those wishing to land goods short of ports where customs would be levied. This commerce was shared among several other markets in that part of Essex. The road west from Prittlewell soon reached the marketplace at Hadleigh, one of several manors (part of the Honour of Rayleigh) granted to Hubert de Burgh in 1228. Hadleigh's market was formally licensed by him three years later; Hubert had built, or was building, a castle there in the preceding years. His widow's challenge against Prittlewell market made no mention of any detriment to Hadleigh market, however, for the latter was a Wednesday event, and thus Prittlewell's was not directly competitive according to the standards applied to legal challenges. Further west were markets at Fobbing, Horndon, and Tilbury. Northwest and northeast of Prittlewell, respectively, Rayleigh's own market was in operation from the same period as Hadleigh's and Rochford's had been licensed by 1257 though its existence is implied in 1235 when Hubert de Burgh was lord of Rochford Hundred. To the east, though at a greater distance, was Great Wakering, a posited Late Saxon minster site, whose market was licensed for Mondays in 1265 (that is, after Prittlewell's had been moved to the other end of the week), though this marked a change of day from the Thursday on which it had apparently been held since a market grant of 1200. Also to the northeast, in Rochford Hundred and on the River Roach, lay the small and dispersed settlement of Shopland, associated with a church and manor-house, where we hear in 1258 that Robert Tybbetoth had instituted a market, for Hugh de Neville, owner of Great Wakering's market, complained that Shopland's was injurious to it. An agreement between the two owners conceded the Shopland market to Tybbetoth, in return for him allocating an annual payment of 9s. to Hugh from a Shopland rent. Still further north were Chelmsford and Maldon.

That commerce frequenting these markets along the Thames Estuary could form the basis for mercantile careers is indicated by the case of John de Priterwell. We first see him in the early 1340s, witnessing London deeds; a few years later he was qualified in such witness lists as 'citizen and apothecary' of London, which suggests that whatever commercial role he had pursued in Prittlewell had prospered enough to enable him to make the move to the richer climes of the capital and set up there nominally as a spicer. One of the deeds he witnessed involved the conveyance of the manor of Southchurch, just east of Prittlewell, and in 1350 he released his own rights in that manor and its appurtenances – although his rights may not have extended beyond lands he personally held of that manor – and in 1351 he was described as 'of Thorpe (Bay) in the parish of Southchurch'. In 1344 he is seen acquiring rights to Horndon property from the heir of a Londoner, and in 1348 £10 worth of quit-rents in the Sussex vills of Icklesham and Guestling; such transactions likely reflect investment of profits John was making from his commercial activities. The 1340s and '50s have also left us evidence of fairly large debts of which John was either debtor or creditor, though we cannot be certain these relate to commercial transactions; none of his own debts resulted in him being sued, and some are explicitly noted as having been paid. In 1348 he stood guarantor for the court appearance of fellow Prittlewell man Reginald le Wyse, who was being sued by law merchant for a sizable debt owed a London mercer, and in the same year he purchased from Reginald a house, 45 acres of land, and 10s. in rents in Prittlewell and Milton – the hundred marks purchase price would have gone a long way to enabling Reginald to settle his debt. The le Wyse family was a prominent one in thirteenth-century Prittlewell, another of its members being described as a tailor, while Henry le Wyse was sued by a London cornmonger in 1344 for a debt of £60.

Unlike Reginald le Wyse, John de Priterwell was a survivor of the Black Death, or at least its first manifestation. Despite land he held in the village of his birth, John's business activities seem to have focused on London, where he had settled by 1332, for in the lay subsidy of that year he was taxed 8d. in Cordwainer Street Ward. Later evidence, however, suggests him a resident either of All Hallows Honey Lane parish, bounded by West Cheap, or of St. Benet atte Wood Wharf in Castle Baynard ward, lying on the Thames – he was an executor of the latter's parish clerk in 1350; possibly he held property in both parishes. In 1364 he was implicated in a perjury case against a butcher, accused of selling John a wey of tallow to take out of London and sell elsewhere – something prohibited by city ordinance, because tallow was a scarce commodity in London. The following year John gave evidence in support of a complaint by three Prittlewell men of extortionate practices by the bailiff at Queenhithe; this suggests he himself was landing goods at Queenhithe. By 1377 he had married Rose, the widow of mercer Robert de Thame, and she was pursuing dower rights in a large property in St. Pancras Soper Lane (Soper being derived from 'shopkeepers') which had frontage on Cheapside that incorporated shops. Although he never rose to aldermannic rank, John was prominent enough within the shopkeeper class to be appointed in 1348 to a commission, made up of representatives of various trades, tasked with putting into effect a royal command to rid Cheapside, Cornhill and other major streets of nuisance clutter arising from the sale of petty goods. In the same year we hear of a poulterer named John de Pritelwelle taking out a 40-year lease of a London property that included an orchard (though a few months later he sub-let it to an ironmonger), but there is nothing suggesting a connection between this John and the like-named spicer.

Rose must have been John's second wife, for her son, Thomas Pritelwell, heir to property John and Rose had held jointly, died a minor in the king's wardship (1390), leaving an older brother John (born ca.1355) as his heir. Rose had died ca.1385, and John senior at some time within the previous few years. John de Priterwell junior already being an active adult by the latter date, the careers of the two Johns overlap a little and it can be hard to distinguish them; both are seen acting together as witnesses to a deed of 1381, conveying land in Prittlewell, Milton, and Southchurch.. However, it was probably John senior who was authorized in 1377 to ship wool along the Thames from Milton to the Westminster staple. And it was specified as John senior who, in 1380, using the excuse of advanced age, purchased a grant of exemption from being appointed against his will to various civic and royal offices or being required to serve on juries or assizes. Though there is little evidence he had been overburdened with such duties in the past, he had been associated in a commission of the peace in Essex in 1352 and he or his son was a commissioner of walls and ditches there in 1379; one or other of them was a commissioner of array in Rochford Hundred in 1385, a tax collector in Essex in 1379 and again in 1382. Such duties were incumbent on larger landholders of the county, and John junior's inheritance included lands in Prittlewell and several other vills in the vicinity (Eastwood, Leigh-on-Sea, Hadleigh), some as part of the manors of Southchurch and Great Wakering. The Prittlewell property included a messuage with garden and curtilage – perhaps suggesting a plot facing onto the marketplace – formerly of Henry le Wyse, and three smaller plots on which six shops had been erected, held of Thomas de Mowbray, earl of Nottingham, to whom lordship of Prittlewell had descended, via marriage, from the de Veres through the Fitz-Alan earls of Arundel. By the time he acquired control of all this (1390) John junior had already conveyed to the vicar of Prittlewell a cottage and various pieces of agricultural land in Prittlewell which had also been part of his inheritance.

John Priterwell junior furthered his social standing by marriage (ca.1375) to Elizabeth, the underage daughter and co-heiress of Thomas de Stapel, one of the king's sergeants-at-arms, who held property jointly with his wife at Prittlewell, Hadleigh, Great Wakering, Shopland and other locations in that region of Essex; Elizabeth came into her inheritance in 1389. John had feet in the two camps of merchant and member of the landed gentry, and was able to translate this into service to Richard II. Whether his father had already forged commercial connections with the Wardrobe, or whether Robert de Vere, Richard's favourite, might have exercised some influence in John's employment, are matters on which surviving records are silent. In 1387 John is described as 'esquire' when recognizing a debt (later paid) of £100 to a London mercer (though he actually only owed half that, and we do not know if it related to a commercial transaction); the descriptor was applied to him on several other occasions.

In 1385, as in later years, he was referred to as 'king's esquire', when rewarded, for services already rendered, with the custody of a Devon heir and his lands. Two years later he was described as yeoman of the king's chapel when appointed, during pleasure, as purveyor of necessaries for the king's works within the palace of Westminster and Tower of London; this furnished him with wages of 4d. a day and a residence within the Tower. If Robert de Vere had in any way been his patron at court, Robert's fall does not seem to have impacted John's prospects; John stood by Richard during the troubled later years of his reign. In 1390 he was able to sponsor a royal pardon for a Little Wakering man accused of killing one of Great Wakering, and he was himself pardoned in 1393 for failure to answer a plea of debt of £136. He was issued protections in 1394 and 1399 to accompany King Richard to Ireland, and was commissioned in 1397 to arrest a supporter of the disgraced Earl of Arundel. In 1396 he was granted 40 marks annually as a retainer in the king's entourage. Henry IV confirmed that grant, and even granted, shortly after his accession, that John should have the farm of the (earl's) manor of Prittlewell, which had been in the king's hands since the banishment of Thomas Mowbray; this may have been short-lived since Mowbray's wife (daughter of Richard Fitzalan) took the manor to a new marriage after Mowbray's death. Yet Priterwell apparently failed to win the new king's full confidence, for Henry explicitly omitted him from those of his retainers who would accompany him to Scotland in 1400, though he was instructed to provide his services to the queen during the king's absence. In 1404 he was implicated in an alleged conspiracy involving the abbots of St. John's Colchester and St. Osyth's, and several prominent Colchester men. 1401 saw his position as purveyor upgraded to a life grant, but in 1409 it was given to someone else, though John was compensated by a grant of 3d. a day wages as a servant of the king's household. In 1407 he had to obtain a royal pardon for failure to appear in the king's court to answer a charge of trespass.

We hear no more of the male line of this Priterwell family. In 1434 the heir of John Priterwell of Shopland esquire and his wife Elizabeth was said to have been their daughter Alice, who in turn left only a female cousin as heir. The family's story shows that although Prittlewell cannot with certainty be said to have been urban, or containing a burghal component, its commerce during the Late Middle Ages was sufficient to nourish the career of a merchant with aspirations of gentrification.