The earliest records of Kellie go back to 1150 where it is mentioned in a charter issued by King David I. The first known owner was Robert of London, the illegitimate son of King William the Lion. None of the early buildings to have survived.
The estate was signed over to a Siward relative, Walter Oliphant, in 1360 and the castle remained in the ownership of the Oliphant family until 1613. It was purchased by Sir Thomas Erskine, who had saved the life of King James VI during the Gowrie Conspiracy. The King stayed at Kellie in 1617 during his only visit to Scotland after the Union of the Crowns, and he appointed Erskine as Earl of Kellie in 1619.
Originally a simple tower house, the lower section of what now constitutes the northwest tower is the oldest part of the castle, dating from around 1360, and is said to be haunted. In 1573 a new tower was built by the 4th Lord Oliphant to the east of the original tower. It is believed that the 4th Lord built the east tower as a jointure-house (a property set aside for the wife after the husband's death) for his wife Margaret. Between 1573 and 1606 the two towers were linked by a new range, terminated by another tower in the south-west, creating the T-plan layout that remains today. The castle is a fine example of Scots Baronial domestic architecture, with an imposing mix of gables, corbelled towers, and chimneys.
The walled garden is 17th century, with late Victorian additions, contains a fine collection of old-fashioned roses, fruit trees and herbaceous plants.
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German crusaders known as the Livonian Brothers of the Sword began construction of the Cēsis castle (Wenden) near the hill fort in 1209. When the castle was enlarged and fortified, it served as the residence for the Order's Master from 1237 till 1561, with periodic interruptions. Its ruins are some of the most majestic castle ruins in the Baltic states. Once the most important castle of the Livonian Order, it was the official residence for the masters of the order.
In 1577, during the Livonian War, the garrison destroyed the castle to prevent it from falling into the control of Ivan the Terrible, who was decisively defeated in the Battle of Wenden (1578).
In 1598 it was incorporated into the Polish-Lithuanian Commonwealth and Wenden Voivodship was created here. In 1620 Wenden was conquered by Sweden. It was rebuilt afterwards, but was destroyed again in 1703 during the Great Northern War by the Russian army and left in a ruined state. Already from the end of the 16th century, the premises of the Order's castle were adjusted to the requirements of the Cēsis Castle estate. When in 1777 the Cēsis Castle estate was obtained by Count Carl Sievers, he had his new residence house built on the site of the eastern block of the castle, joining its end wall with the fortification tower.
Since 1949, the Cēsis History Museum has been located in this New Castle of the Cēsis Castle estate. The front yard of the New Castle is enclosed by a granary and a stable-coach house, which now houses the Exhibition Hall of the Museum. Beside the granary there is the oldest brewery in Latvia, Cēsu alus darītava, which was built in 1878 during the later Count Sievers' time, but its origins date back to the period of the Livonian Order. Further on, the Cēsis Castle park is situated, which was laid out in 1812. The park has the romantic characteristic of that time, with its winding footpaths, exotic plants, and the waters of the pond reflecting the castle's ruins. Nowadays also one of the towers is open for tourists.