Henry VIII was a regular visitor to the Palace of Esher and he had it annexed to his Hampton Court riding circuit.It is known that Henry VIII was at Esher as a guest of either Wolsey or Bishop Fox on All Souls Day in 1517, as an offering of 6s. 8d was recorded. This may either have been an offering in church, or more probably, a gratuity to the servants.

According to Jane Porter, (a novelist, whose source is unknown but who resided at a property called the Alderlands on the High Street, Esher in the 19^th century), Henry VIII observed with surprise from the summer house at Esher the advancement of grandiose building works on the opposite banks of the River Thames at Hampton Court, which “compelled the ambitious architect to couch his premeditated presumption, under the finesse that it was intended to be a humble offering from a poor but grateful servant, to his most august liege lord the King.” The offering was accepted, but how little of the intention was believed remains a mystery. However, on 23 September 1528, Sir William Fitzwilliam (alderman and sheriff of London and treasurer and chamberlain to Wolsey), wrote to Wolsey on the King’s behalf demanding that he vacate the house at Hampton Court for four days, so that the King could receive a papal legate there. This was the first time that Henry made any claim on the house and from then on he and Catherine (not to mention Anne Boleyn) used the house regularly. As far as is known, Wolsey visited the house only three times thereafter and then as a refugee. It would seem that Henry suspected Wolsey’s contrary intentions and used his royal position of authority and the memory of their conversation at Esher for strong grounds to demand it and his subsequent failure to return it. Furthermore, by March 1529, Henry was paying for his own alterations there and significantly, it was not included in the list of properties in Wolsey’s inquisition post mortem taken in 1530.

On 16 September 1537, Henry’s third Queen, Jane Seymour, ceremonially took to her chamber at Hampton Court for her confinement on account of her advanced stage of pregnancy. Meanwhile, Henry moved with his riding household to Esher to minimize the risk of exposure to the plague, which was prevalent. From Esher he eagerly awaited news of the birth and issued orders for a garter stall to be prepared at Windsor for the expected Prince. On 12 October 1537, the Queen gave birth to the long-awaited Prince and heir to the Tudor dynasty. However, the celebrations were cut short as, before her son was more than a few days old, Queen Jane contracted puerperal fever, probably as a result of unhygienic obstetrics and died on 24 October. The King was at Hampton Court at the time, having postponed a hunting trip to Esher to be at her side. Upon her death he immediately left for Whitehall to grieve privately; behaviour which was in stark contrast to his demeanor following the deaths of his two previous wives, when he had appeared unmoved.

The King’s increasing size caused him difficulties in travelling to Windsor for stag hunting and, as the estate of Esher was more convenient, he decided it should become his hunting box. He therefore resolved to constitute Hampton Court an “honour” and to make a “chase” around it; he acquired several neighbouring estates, including that of Esher. In 1538, (as referred to in Rymer’s Foedera), Gardiner conveyed to the King “his manor of Asher, in Asher, Ditton, Cobham, Kingston and Walton, William Basyng, alias Kingswell, prior of the monastery and cathedral of St Swithin, at Winchester, confirming the deed.” The Manor and other lands were annexed to the “honour and chase at Hampton Court” in 1540. The park was promptly stocked with 120 quick deer and 80 with antlers at 3s.4d each.

The last time that Henry VIII resided at Esher was in December 1546, when, not fully recovered from a severe bout of fever, he left nearby Oatlands and stopped at Esher, Nonsuch and Wimbledon on his way to Whitehall. His condition was so poor that the journey to London had to be made in slow stages. The King died in the early hours of the morning of Saturday, 29 January 1547.