In 1911, Theodate Pope Riddle, famous for designing Hill-Stead in Farmington, completed plans for another country estate for her friends, Joseph and and Elizabeth Chamberlain. In 1909, the Chamberlins had acquired land in Middlebury, close to Whittemore estate. Their house, called “Highfield,” was constructed in 1911-1914, on a hill above Lake Quassapaug. Theodate’s design for the house was influenced by her recent trip to England, where she had studied traditional village architecture and the work of English Arts and Crafts architects like Edwin Lutyens. Designed to resemble a rustic English cottage, Highfield has a large interior, with the second story cleverly concealed behind the sloping shingled roof. Next to the house is a sunken garden, where Theodate created a sumer house with removable glass walls. Charles Downing Lay made alterations to the back of the house in 1925 and to the attic in 1929. In 1954, the Stillman family, who had suceeded the Chamberlins as owners of the house, sold the property, which became a nine hole golf course. The house is now the clubhouse.