The Highfield house is a historic building located in Middlebury, Connecticut. The House, surrounded by over 600 acres of land, was the former summer estate of Columbia University law professor Joseph and his wife, Elizabeth Chamberlain. They commissioned Theodate Pope Riddle, one of the first licensed female architects in America to build this comfortable English Arts and Crafts style cottage on a hill above a lake. It is likely that after the Westover School was completed in town, the Chamberlains were excited to see how Theodate could design them a summer house in the similar Arts and Crafts style. The estate was completed in 1914 and stands two-stories with the second floor concealed within the steeply pitched gable roof. Like Westover, the building was stuccoed. In the 1950s, the estate was purchased by a group of individuals who dedicated the complex as a family and country club with golf, tennis courts, and pool. It is known as the Highfield Club today.