The present designed landscape was laid out in the first half of the 19th century on the site of a previous 17th century landscape laid out by the 3rd Earl of Winton. It was seriously affected by necessary war-time operations but has since been partially restored.
Earliest records of Winton go back to the De Quincey family who resided at Winton during the reign of Alexander I (1108-1124). A daughter of the family later married one of the de Saytens, later Seton, who were granted lands in East Lothian by David I (1124-53). The estates of Seton and Winton were joined during the reign of William the Lion (1165-1214).
George, 4th Lord Seton, began the 1st phase of building at Winton c.1480. Maitland's 'History of the House of Seton' describes the ornamental garden of Winton at that time as having flower plots which were surrounded by a hundred painted wooden towers or temples, surrounded by gilt balls. The 4th Lord Seton died in 1508 and the Castle was burnt down by the English forces c.40 years later leaving only the barrel vaulted ground floor and the walls up to the third floor and above.
The Seton family, loyal to the Stuart kings, were granted an Earldom in 1600. Soon after, restoration work began on the Castle but this ceased on the death of the first Earl in 1603. His son Robert, the 2nd Earl, inherited extensive debts which his father had incurred restoring the property for him. He, in fact, resigned his title in favour of his younger brother, George, the 3rd Earl, who c.1620 commissioned William Wallace to fully restore the Castle. Winton became the Dower House and Seton Palace remained the main residence for the family.
It is recorded, that the Earl 'founded and built the great house from its foundation wall with all the large park, orchard and gardens there'. That he built the house from foundation level has been disputed and the only evidence of the designed landscape is provided by General Roy's map of c.1750 when enclosed areas are shown to the north and south of the Castle. Also indicated is the village of Winton which was originally sited to the north of the Castle but was moved in the mid-19th century, c.1853.
The 5th Earl, George, was a Jacobite who forfeited the estates after the 1715 uprising and he fled to Rome to escape execution where he died, unmarried, in 1749. The forfeited estates were acquired by the York Building Company and a period of neglect fell on the landscape which lasted until 1779 when the Company went bankrupt and the Winton estate was acquired by Mrs Hamilton Nisbet, who also owned the lands of Belhaven, Dirleton and Pencaitland. Her younger son, Colonel John Hamilton, inherited the estate on her death in 1797 and began what is generally regarded as the second phase of building in the Castle. Forrest's map of East Lothian surveyed in 1799 marks Pencaitland House as the residence of Colonel Hamilton, while Winton does not even have a name. What remains of the avenue to Pencaitland House has since been included as part of the parkland at Winton. The mansion part of Pencaitland House was burnt down in 1876 leaving the two pavilions, now separate dwelling houses. Colonel Hamilton also planted extensively in the grounds prior to his death in 1804. The estate then passed through the female line of the family until 1846 when it was inherited by Lady Ruthven. She made extensive improvements to the grounds shown on the 1st edition OS map of 1863 which included the resiting of the village of Winton to its present situation to the north-west of the Castle. Sir Walter Scott is said to have modelled Ravenswood Castle in his 'Bride of Lammermoor' on Winton Castle.
In 1885, Constance Nisbet Hamilton succeeded and, three years later, she married Henry Ogilvy, 2nd son of the 9th Baronet of Inverquharity by his second marriage. On her death in 1920, the estate passed to a nephew of her husband, Gilbert F.M. Ogilvy. An architect by profession, he removed part of the Regency extension on the east side of the Castle. During World War II, the west park was ploughed. Most of the woodlands were cut down and replanted in the 1950s and '60s. Gates in the garden and at both lodges were brought to Winton from Bloxholm in Lincolnshire, which Mrs Nisbet Hamilton Ogilvy inherited from her ancestor, General Lord Robert Manners, son of the 2nd Duke of Rutland. In 1953, the estate passed to his son, David, who three years
later inherited the title of 13th Baronet of Inverquharity from an uncle. He continues to farm the estate and has replanted the woodlands. The house was one of the first properties to benefit from grant-aid on the formation of the Historic Buildings Council. Since then, it has been partly converted into flats.