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21 Schoolhouse Road

Hillsdale, NY 12529
  • $21,000,000
  • STATUS: Active
  • MLS #: 1040841
UPDATED: 42 min ago
$21,000,000
  • 5
    BEDS
  • 135
    ACRES
  • 6
    BATHS
  • 1
    1/2 BATHS
  • 5,203
    SQFT
  • $4,036
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2020
County:
Area:

School Information

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.

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© 2026 OneKey MLS. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or This Old Hudson Team at Houlihan Lawrence. Data last updated: 2026-10-16T22:20:40.473.
www.thisoldhudsonrealestate.com/homes/180861860
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21 Schoolhouse Road Hillsdale, NY 12529

  • Price: $21,000,000
  • Status: Active
  • On Site: Days
  • Updated: 42 min ago
  • MLS #: 1040841
5
Beds
6
Baths
1
½ Baths
135
Acres
5,203
SQFT
$4,036
$/SQFT
2020
Built
Neighborhood:
Hillsdale
County:
Columbia
Area:
Hillsdale
Elementary School:
Taconic Hills Elementary School
Middle School:
Taconic Hills Junior/Senior High
High School:
Taconic Hills Junior/Senior High
School District:
Taconic Hills
Property 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.
Exterior Features

Architectural Style FarmhouseModernOther Carport YN No Construction Materials Wood Siding Garage YN Yes Levels One Parking Features DrivewayPrivate Pool Private YN Yes Property Attached YN No View LakeMountain(s)Panoramic Waterfront YN No

Interior Features

Appliances DishwasherDryerGas RangeOvenRangeRefrigeratorStainless Steel Appliance(s)Washer Attic See Remarks Basement Details Unfinished Basement YN Yes Cooling Central Air Fireplace YN Yes Fireplaces Total 2 Flooring Hardwood Interior Features First Floor BedroomFirst Floor Full BathHigh CeilingsKitchen IslandOpen FloorplanPrimary BathroomMaster Downstairs Rooms Total 20

Property Features

Association YN No Down Payment Resource YN No Heating See Remarks Horse YN Yes Lease Considered YN No Other Structures ArenaBarn(s)Garage(s)Guest House Property Sub Type Single Family Residence Senior Community YN No Sewer Septic Tank Special Listing Conditions None Tax Annual Amount 52890 Tax Source Municipality Utilities See Remarks Water Access YN Yes Water Source Other

Listing courtesy of Jonathan R. Stein of Douglas Elliman Real Estate: 914-232-3700
© 2026 OneKey MLS. All rights reserved.


© 2026 OneKey MLS. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or This Old Hudson Team at Houlihan Lawrence. Data last updated: 2026-10-16T22:20:40.473.
 
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This Old Hudson Team at Houlihan Lawrence
Hudson NY, 12534