Without question, this property is the most photographed site in the tiny town of Pomfret, Vermont, if not the state. The property dates to the late 18th century when John and Samuel Doten moved to the newly settled town of Pomfret Vermont, overlooking the growing town of Woodstock in the valley below. The two brothers acquired vast farmland on the hills of Pomfret and each built farmhouses adjacent to eachother, with Samuel getting elevated land and John developing the land sunken off what is now known as Cloudland Road into this stunning property. Sleepy Hollow Farm remained in the Doten family for centuries until the 1950s, when the owners sold the property to move to Woodstock and work for Laurance Rockefeller, the famous philanthropist and conservationist, who later donated his Summer home in Woodstock to the National Park Service. The property sold numerous times in the late 20th century, and is presently owned by Aerosmith guitarist Joe Perry and his wife, Billie. They are clearly great stewards to the property’s rich history and various outbuildings, and must not care too much to have swarms of photographers at the end of their driveway year-round!