This is an aerial shot of the farm at 104 Dekay Road. My father ran this farm in partnership with James and Cassie Park. It had a small dairy and four apple orchards. I spent part of my youth working on the farm. Don't know when the photo was taken, but the road looks like it was a dirt road.

On the 1850 map I can see three dots which probably represent the house, carriage house and barn, but with no owner listed. ON the 1863 map James Green is listed as the owner with N.K. Wood as the resident. On the 1875 map, George Cary is listed as the owner. On the 1875 map R.W. Dekay is listed as the owner. And on the 1903 map George Carey continues to be the owner.

My father currently owns the farm and has in his possession a number of the old deeds. According to www.orangecounty.gov, the current farm consists of two parcels: 31.30 acres and 14.30 acres. They have the house as being built in 1800, which is quite possible. My brother took 5 acres on which he built a house, which he no longer owns. That means the farm at the time was about 50 acres.

The 1863 map claims the property being 40 acres, with Dekay Rd. splitting the property somewhat like it is currently, which doesn't make too much sense. The 1903 map also claims that the property is 40 acres.

Here is what I learn from the old deeds that Dad has:

April 4, 1848, Ezra Sanford and wife Adeline to James Green for $2350; 39.10 acres.
There was a note on the above deed. Sophia Green to Robert Dekay $3200.
April 12. 1888 Robert W.Dekay and wife Elizabeth to George Carey $3650: 39.10 acres.
April 1, 1907 George and Frances Carey to James Park $4000; 39.10 acres.

This is the second parcel:

Oct. 15,1911 Harry Vail and Cecial Vale and Fred C.Carey to John Pelton $900; 14.31 acres.
April 1, 1918 John and Martha S.H. Pelton to James Park $1200; 14.31 acres.
Dad got the farm on Jan. 30, 1973.

This is what one has to go through to date a house. And then you might run into this. The Warwick Advertiser published an Obit for Lansing Haight Sanford, son of George W. Sanford. He was the eldest son of G.W.Sanford. And was born on the Robert Dekay farm (now owned by George Carey) near New Milford on Oct. 1847. From his birthplace he removed with his parents in 1848 to the homestead at the beginning of Maple avenue, where he was reared, and where his parents lived.
afterwards."

This is about as far as I can go with data at the present time. I enjoy doing history mystery.