Briarcliff Manor
This is one of a few areas with a Briarcliff address and Ossining schools. This section was built out primarily in the 1960s, with gently…
Chilmark
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…
Crotonville
Crotonville as recently described by one resident: “Crotonville is not an official place – it is more a state of mind.” Crotonville is situated on…
Indian Village
The original developers were quite cute and gave all the streets Native American names, so the area became known as Indian Village. The initial homes…
Morningside Drive
Morningside is in the Town of Ossining and the Ossining School District, but much of the area has a Briarcliff address. The topography is rolling,…
New Castle
The New Castle section of Ossining started out as farmland and large estates. It was mostly subdivided into one and two acre parcels, although quite…
North Village
The North Village of Ossining starts with some smaller homes and continues along to much larger properties. Cedar Lane runs through the middle of the…
Old Village
The Old Village of Ossining is bounded by the Hudson River and Route 9 and always has been the beating heart of our community. Here…
Scarborough
Scarborough is a hamlet located in the Town of Ossining, the Village of Briarcliff and the Ossining School District. It started as mostly large estates.…
Sherwood Park
The signature 1920s homes and broad sweep of Sherwood Ave set the tone for Sherwood Park, an area of quiet streets and sidewalks. Although homes…
Somerstown Road
Somerstown Road is a neighborhood unto itself, as it was originally pretty much the only thoroughfare in the area other than farm roads. Some of…
Sparta
In precolonial times Sparta was a separate village with a busy port. It was a bustling place, and was shelled by the HMS Vulture warship…
Stonegate
Stonegate “North” and Stonegate “South”: A major Westchester developer put in developments in a number of communities and put Stonegate Road in each of them,…
Sunset Hill
In the 1920s on the outskirts of the Ossining Village, Sunset Hill was subdivided into 1/3 acre lots, and some classic Romance Style homes were…
Tappan Terrace
The original Haymount House was built by Wall Street financier William Fuller with a Southern Antebellum motif to remind him of his hometown in North…
Tavano Road
Roy Johnson, a direct disciple of Frank Lloyd Wright, bought a picturesque section of land in the Town of Ossining that was divided off from…
Torbank
An international merchant trader built Torbank, a 6,458 s/f Federal Style brick mansion with a distant river view. The orchards, meadows and gardens of the…
Upper Village
The Upper Village was originally farms, and soon became Ossining’s first expansion area as it grew outward from the Old Village. In the mid 1800s,…
Veterans Park Area
Walk to Veterans Park! Arguably the most kid-friendly neighborhood in Ossining, there is a backlog of people looking to live here, many of whom grew up…
Village Co-op Area
The “Village Co-op Area” is an area off South Highland Ave across the street from Nelson Park and up the street from Arcadian Shopping Center.…
Waterview
Waterview is a large lot subdivision started in the late 1990s. The developers had the vision to cluster the homes in order to preserve as…
Yorktown Section
Nature preserves, large gentleman’s farms, some with horse facilities, and Fable, with its farm to table organic crop share, set the theme for the Yorktown section of…