One of the great neighborhoods in Ossining is known as the Indian Village. All of the streets have tribal names, such as Mohawk and Seneca Roads. I happened to grow up on Osage Drive. Although most of the streets are pre war, the majority of the homes are baby-boom era housing. In that respect the place is a bit like Levittown on Long Island; the original homes are slowly giving way to larger, expanded structures.
Here are two homes on my street that are more or less in their original footprint. They happen to be the homes across the street from where I lived.
Here are two more homes. The ranch in the foreground is pretty typical of an original home. The one to the left was recently expanded. That white home peeking out back to the far left is my old house. My father put on three additions. I added a fourth.
I was told that the neighborhood was an estate and peach grove. There is a huge apartment house across the street from my old home that was known as the Mundet Mansion (we called it the apartments). It had fallen into disrepair when I was a kid, but the guy who bought it in the early 70's brought it back beautifully. It is a striking building. I saw it every day of my life growing up in that home. It is worth two photos.
The Indian Village is a wonderful neighborhood to call home. I freely admit my bias, as I still live walking distance from my old neighborhood in nearby Chilmark, on the other side of the Reservoir. I used to ride my bike between the neighborhoods (It was a Murray 5 speed with a banana seat, high handlebars and a fat rear tire). If you are thinking of living in Ossining, check it out. You'll be glad you did.