21 Schoolhouse Road, Hillsdale, NY 12529 (MLS # 20265125)

There are beautiful homes in the Hudson Valley, and then there are properties that seem to occupy a world entirely their own. Set at one of the most extraordinary vantage points in the region, this exceptional contemporary estate presides over 135 private acres with sweeping, unobstructed views across the Hudson Valley to the Catskill Mountains. The sense of scale is remarkable: open sky, rolling land, distant mountains, and complete privacy in every direction--yet Hudson and Great Barrington are each only 25 minutes away. The residence was designed around this landscape; dramatic walls of glass frame the Catskills throughout the house, while soaring ceilings and expansive, open living spaces give the interiors a sense of volume without sacrificing warmth. Living, dining, and kitchen spaces unfold effortlessly toward the terrace and infinity pool, where the water appears to disappear into the mountains beyond. The entire home lives on a single level, an increasingly rare luxury at this scale. Two primary suites and three additional ensuite bedrooms create five beautifully private bedroom suites, equally suited to intimate everyday living or a house full of family and friends. Throughout, the architecture is sophisticated but restrained, allowing the extraordinary setting to remain the focus. And the house is only the beginning. The estate encompasses 135 acres of lawns, fields, woods, and private trails, creating a property that can be experienced as much as admired. A large, crystal-clear swimming pond offers an idyllic counterpoint to the infinity pool. Miles of trails wind through the acreage for riding, hiking, and exploring, while a barn and riding arena establish the property as a true equestrian retreat. A separate two-bedroom cottage provides charming guest accommodations, while a carriage house with its own apartment creates additional flexibility for guests, staff, an office, or studio. What ultimately distinguishes this property, however, is something photographs and specifications can only begin to convey: the feeling of being here. Morning light moving across 135 private acres. Long afternoons by the pond. Horses on the trails. Dinner overlooking the mountains. And, each evening, the sun setting behind the Catskills from an infinity pool seemingly suspended above the Hudson Valley. It is extraordinarily private without being isolated, grand without being ostentatious, and remarkably complete without feeling overdone. Properties of this caliber are exceedingly difficult to create--and even harder to find. Just 25 minutes from the restaurants, galleries, shops, and cultural life, this is not simply a country house. It is one of those rare places that makes leaving the city feel like arriving somewhere else entirely.

Last Updated	9/3/2026	Year Built	2020
Community	Hillsdale	Garage Spaces	4.0
County	Columbia

Additional Details

AIR	CENTRAL AIR
AIR CONDITIONING	Yes
APPLIANCES	Built-In Gas Range, Built-In Refrigerator, DISHWASHER, DRYER, Electric Water Heater, RANGE HOOD, WASHER
AREA	Hillsdale
BARN/EQUESTRIAN	Yes
BASEMENT	UNFINISHED, Yes
CONSTRUCTION	Wood Siding
EXTERIOR	Fire Pit, Lighting, Private Yard
FIREPLACE	Yes
GARAGE	Yes
HEAT	FORCED AIR, HOT WATER, Propane
INTERIOR	High Speed Internet, Master Downstairs
LOT	135 acre(s)
LOT DESCRIPTION	Agricultural, Cleared, Gentle Sloping, LANDSCAPED, Many Trees, Pasture, SECLUDED, Sloped, Views
LOT DIMENSIONS	135.0
POOL DESCRIPTION	Gunite, In Ground, Infinity
SEWER	Septic Tank
STORIES	1
STYLE	Contemporary
TAXES	52890
VIEW	Yes
VIEW DESCRIPTION	Pond, Panoramic, Pool, Pasture, Ridge, Skyline

Location

 

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