Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
Listing photo for 21 Schoolhouse Road, Hillsdale, NY
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21 Schoolhouse Road,

Hillsdale, NY

$21,000,000

5 Beds
5½ Baths
5,203 Sqft
135.00 Acres
4 Garages

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.

Facts & Features
MLS® # 20265125
Price $21,000,000
Bedrooms 5
Bathrooms 5.50
Full Baths 5
Half Baths 1
Square Footage 5,203
Acres 135.00
Year Built 2020
Type Residential
Sub-Type Single Family Residence
Style Contemporary
Status Active
MLS ucbr
Community Information
Address 21 Schoolhouse Road
Area Hillsdale
City Hillsdale
County Columbia
State NY
Zip Code 12529
Amenities
# of Garages 4
View Pond, Panoramic, Pool, Pasture, Ridge, Skyline
Is Waterfront No
Has Pool Yes
Pool Gunite, In Ground, Infinity
Interior
Interior Features High Speed Internet
Appliances Built-In Gas Range, Built-In Refrigerator, Dryer, Dishwasher, Electric Water Heater, Range Hood, Washer
Heating Forced Air, Hot Water, Propane
Cooling Central Air
Has Basement Yes
Basement Unfinished
Fireplace Yes
# of Fireplaces 2
Fireplaces Library, Living Room
Stories One
Exterior
Exterior Wood Siding
Exterior Features Fire Pit, Lighting, Private Yard
Lot Description Agricultural, Cleared, Gentle Sloping, Landscaped, Many Trees, Pasture, Secluded, Views
Roof Metal
Construction Wood Siding
School Information
District Taconic Hills Central Schools
Additional Information
Date Listed September 3rd, 2026
Days on Market 32
Zoning Residential
Short Sale No
RE / Bank Owned No
Listing Details
Listing Courtesy of Stone House Properties, LLC
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