In 1949, Plandome Heights annexed an area adjacent to and immediately east of the village, called Chester Hill; this area is at the southeastern end of Plandome Heights, east of Plandome Road, and includes streets such as Chester Drive and Winthrope Road.
In 1949, Plandome Heights annexed an area adjacent to and immediately east of the village, called Chester Hill; this area is at the so,utheastern end of Plandome Heights east of Plandome Road, and includes streets such as Chester Drive and Winthrope Road.