Content Farm was owned by the Law family (not sure if they built it), I think as far back as “Strong Oak” Law (I think I got nickname right) Around the turn of the 20th century there was Robert Law and the two Law Sisters: Sallie Law Williams and Anna Law Wright. The attached newspaper article is about Armstead Peter, the grandson of Laurence and Sallie Williams.

Sallie Williams funded much of the construction of the Cambridge Library in 1903. In 1906 Sallie and Anna invited their friend Mr Tiffany to Cambridge to remodel the windows in St Luke’s church.
On the map, I’ve marked where the “old road” used to go from Content Farms over the hill to Northwood (the estate of Robert McClellan on North Union, next to Woodlands Cemetery, now owned by Common Sense). I can’t recall offhand the significance of that road, but for some reason it sticks in my head and pops up whenever someone asks me about Content Farm.
We can see the Content Farm “mansion on the hill” on the west side as you drive along Content Farm Rd. The other portion of the estate, named Southview, is on the other (the east) side of Content Farm Rd, back behind the trees, not really visible from the road. If you go to the top northwest corner of Woodlands Cemetery, poke through the trees, you can get a nice view of Southview if you bring your binoculars.
Jack Metzger (Jack’s Outback Antiques across from the bank) for many years has been helping Louisa catalog things in the Southview estate. She’s a descendant of Armstead Peter but I can’t recall the connection.
One final tidbit. Armstead Peter IV was in Union College in the 1980s. He came to Cambridge to learn about his family. He wrote a dissertation about Content Farm. I think he gave a copy of his report to someone here, maybe the Cambridge Historical Society.