Chilmark Neighborhood in Ossining |


This 300-acre gentleman’s farm was assembled in the late 1800s by V.E. Macy. A descendent of the Nantucket Macy family, he possessed a huge fortune acquired from his family’s involvement in whaling, international shipping and oil (his father sold their oil company to Standard Oil).

Around the turn of the 20th Century he embarked on a development project and divided much of the property up into minimum 1/4-acre lots. It was designed as a romantic suburb with gracefully winding roads to blend in with the natural surroundings and to give the effect of a tranquil oasis from city living. Extra care was given to the choice of landscaping – V.E. planted the iconic linden trees along Underhill Road.

To preserve the look and value, the types of homes that could be built were limited to revival styles – Tudor, Colonial and Gothic, to name a few. They also required the builders to use their architect. He built an 8.3-acre country club for the residents, which is now owned by the Village of Briarcliff and called the Chilmark Park.

Everyone enjoys driving through Chilmark. Its distinctive presence is literally the masterwork of an exceptional man and his vision.

Pictures of Chilmark

Chilmark Homes for Sale and Market Info

Below you’ll find single-family houses currently for sale in Chilmark. Additionally, you can…

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