The round stone structure up the hill was a cistern that held the water supply for the main house. The grey stone building is a schoolhouse, built in 1826 for John Jay's grandchildren; inside it is an exhibit about the building's history. The small white clapboard building is a playhouse, constructed in 1925 by Eleanor Jay Iselin for her young son. The rectangular, flat area north of the playhouse was the location of a tennis court, built in the early 20th century. In the mid-19th century, an orchard of pear trees grew in this area.
