$21,000,000
 $112,733 est/mo Sourced by Back At You

21 Schoolhouse Road,Hillsdale, NY 12529

Hillsdale, NY 12529

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Description

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.

Details

MLS #1040841
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusActive
Year2020
Days On Site68
Listing Provided ByDouglas Elliman Real Estate | Jonathan R. Stein

Features

Bed(s)5
Bath(s) 7 Total
SQ Feet5,203
Garage3
BasementY
PoolYes
Story(s)1
Acreage135.00
Water FrontYes
Property ViewLake, Mountain(s), Panoramic

Interior

CoolingCentral Air
HeatingSee Remarks
Interior FeaturesFirst Floor Bedroom, First Floor Full Bath, High Ceilings, Kitchen Island, Open Floorplan, Primary Bathroom, Master Downstairs
AppliancesDishwasher, Dryer, Gas Range, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer

Exterior

Construction MaterialsWood Siding

Parking

Garage Yes / NoYes
Parking FeaturesDriveway, Private

Utilities

UtilitiesSee Remarks
SewerSeptic Tank

Taxes

Tax Year2025
Tax Assessed Value2878700
Tax Annual Amount52890

Area Information

StateNY
CountyColumbia County
CityHillsdale
Zip Code12529
School DistrictTaconic Hills Junior/Senior High
Elementary SchoolTaconic Hills Elementary School
High SchoolTaconic Hills Junior/Senior High
Listing VS Median (in 12529)
Price:
$21,000,000
low | high
Med:
$698,000
100% of Average
sqft:
5,203
low | high
Med:
2,040
100% of Average
$ / sqft:
$4,036
low | high
Med:
$342
100% of Average
On site:
68
low | high
Med:
117
58.119658119658% of Average
Sourced by Back At You

Market Activity 12529

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Learn More About This Property

StateNY
CountyColumbia County
CityHillsdale
Zip Code12529
School DistrictTaconic Hills Junior/Senior High
Elementary SchoolTaconic Hills Elementary School
High SchoolTaconic Hills Junior/Senior High
Listing VS Median (in 12529)
Price:
$21,000,000
low | high
Med:
$698,000
100% of Average
sqft:
5,203
low | high
Med:
2,040
100% of Average
$ / sqft:
$4,036
low | high
Med:
$342
100% of Average
On site:
68
low | high
Med:
117
58.119658119658% of Average
Sourced by Back At You
Listing Updated: September 28, 2026 at 8:47:44 PM PDT
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