21 Schoolhouse Road, Hillsdale, NY 12529
Local realty services provided by:ERA Top Service Realty
21 Schoolhouse Road,Hillsdale, NY 12529
$21,000,000
- 5 Beds
- 7 Baths
- 5,203 sq. ft.
- Single family
- Active
Listed by: jonathan r. stein
Office: douglas elliman real estate
MLS#:1040841
Source:OneKey MLS
Price summary
- Price:$21,000,000
- Price per sq. ft.:$4,036.13
About this home
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....
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Home facts
- Year built:2020
- Listing ID #:1040841
- Added:3 day(s) ago
- Updated:September 07, 2026 at 11:02 AM
Rooms and interior
- Bedrooms:5
- Total bathrooms:7
- Full bathrooms:6
- Half bathrooms:1
- Rooms Total:20
- Flooring:Hardwood
- Kitchen Description:Dishwasher, Kitchen Island, Oven, Range, Refrigerator, Stainless Steel Appliance(s)
- Bedroom Description:First Floor Bedroom, Master Downstairs
- Basement:Yes
- Basement Description:Unfinished
- Living area:5,203 sq. ft.
Heating and cooling
- Cooling:Central Air
- Central air:Yes
Structure and exterior
- Year built:2020
- Building area:5,203 sq. ft.
- Lot area:135 Acres
- Architectural Style:Farmhouse, Modern
- Construction Materials:Wood Siding
- Levels:1 Story
Schools
- High school:Taconic Hills Junior/Senior High
- Middle school:Taconic Hills Junior/Senior High
- Elementary school:Taconic Hills Elementary School
Utilities
- Sewer:Septic Tank
Finances and disclosures
- Price:$21,000,000
- Price per sq. ft.:$4,036.13
- Tax amount:$52,890 (2025)
Features and amenities
- Appliances:Dishwasher, Dryer, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
- Laundry features:Dryer, Washer
- Amenities:High Ceilings, Open Floorplan
Parking
- Parking description:Driveway, Private
- Garage:Yes
- Garage spaces:3
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