Stump Grinding in Plandome Heights

In the early 20th century, Benjamin N. Duke of the Duke tobacco family developed large parts of what is now Plandome Heights through the Plandome Heights Company, which was one of Duke’s real estate ventures; many of these homes were built in the Spanish style, which was a popular architectural style at the time. The Duke family owned large portions of Plandome Heights in the early 20th century.

Prior to incorporating, the residents in the original part of Plandome Heights (the western and central portions) had unsuccessfully petitioned for neighboring Plandome to annex their area. This resulted in residents deciding to incorporate following Plandome’s refusal, and Plandome Heights officially became a village on June 11, 1929.

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.