Schoolhouse Ridge

Twenty one Schoolhouse Road runs up a private drive to the top of a ridge in Hillsdale, in the eastern corner of Columbia County where the Taconics fall away west toward the Hudson. From the lawn the land drops and keeps dropping, over hayfields and woods and a long swimming pond, out to the Catskills on the far horizon. There is nothing built between the house and the mountains.

The estate covers 135 acres across four contiguous parcels, most of it in Hillsdale with the southern end crossing into Austerlitz. Hudson is twenty five minutes west. Great Barrington is twenty five minutes east.

The residence was completed in 2020 by its original owner, who conceived and built it entirely for personal use with no intention of bringing it to market. It was not a speculative project. It was a house made over time for the person who meant to live in it, and it reads that way.

You see it in the quality of the construction, in the generosity of the proportions, and above all in the way the building answers its setting. The architecture was drawn around the land and the view rather than imposed on them. The result is highly considered and, for a house of this scale, remarkably comfortable.

The entire house lives on a single floor, which at this size is close to unheard of. Living, dining and kitchen open into one another and run out to the terrace and the infinity pool, where the water reads as though it ends at the mountains.

Ceilings reach forty five feet at the ridge, and the volume is the point: the house is enormous overhead and still entirely walkable, with no stair between one room and the next.

There are five bedroom suites, including two primaries, each with its own bath. Glass runs the length of the west elevation, so the Catskills are in the room whether you are cooking, working or asleep. Below grade there is another 2,300 square feet finished.

Miles of private trails wind through the acreage for riding, hiking and walking. A barn and riding arena make it a working equestrian property. The swimming pond below the house is large enough for a dock and a canoe and clear enough to swim all summer.

Lawns give way to hayfields and hayfields give way to woods, and the whole of it is yours to the treeline in every direction.

A separate two bedroom log cottage sits in its own clearing with a porch facing the field. A carriage house holds substantial garaging and its own apartment above, with a kitchen, a sitting room and a bath.

Both are close enough to the main house to feel part of the place and far enough away that a full house never feels like one.

Large contiguous tracts do still come to market in the Hudson Valley. Estates of this completeness do not. The pond, the equestrian facilities, the cottage, the carriage house, the trails and the infrastructure already exist, and none of it costs the property its privacy or its quiet.

You can find a great house here. You can find a great view. You can find real acreage. Finding all three on one ridge, twenty five minutes from both Hudson and Great Barrington, is the part that almost never happens.

If you would like to submit your property to The Full Ask, please visit our submissions page. Featured properties are introduced to our community of agents, designers, and buyers who care about well-considered real estate.