Steephill was the location of a country estate since the time of Hans Stanley, governor of the Isle of Wight, who built there in landscaped surroundings a rustic-style house called The Cottage during his first term of office 1764-1768.
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His daughter, the novelist Pearl Mary Teresa Craigie (pseudonym "John Oliver Hobbes") lived near the Castle from 1900–1906, writing a number of her works there.
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After his death the estate was purchased by Wilbraham Tollemache.