Hever Castle in Kent unveils rare Tudor pictures
The most rare is a portrait of Henry's older brother Arthur, Prince of Wales, painted in 1500, the year before his marriage to Catherine of Aragon.
The other is of the brothers' father, King Henry VII, painted in about 1506, towards the end of his life.
The portraits were unveiled on Monday by writer and historian David Starkey.
Dr Starkey said the pictures filled one of the biggest gaps in the collection at Hever, near Edenbridge.
They dated from a pivotal time in English history.
If Prince Arthur had not died and had become king, his brother would not have married Catherine, there would have been no love affair between Henry VIII and Anne Boleyn and no Reformation.
The picture of Prince Arthur, which hung for many years in the National Portrait Gallery, is the only surviving portrait which could have been painted in his lifetime.
Dr Starkey said it was "exquisite - very finely painted" and of international significance.
The portrait of Henry VII was a "fairly standard" likeness of the king and not of the same quality.
Both were painted by Flemish craftsmen who were attracted to the powerful and wealthy new English court.
They were bought for the Hever collection and were "very valuable", said Dr Starkey.
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