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21 Schoolhouse Road

Hillsdale, NY 12529
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Bed 5

Bed

Bath 7

Bath

SqFt5,203

Sqft

Acres135

Acres(Lot)

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 spac es 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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Detail Ic Property Details

Property Type : Residential

Price : $21,000,000

AD Id : 90999526

MLS Id : 1040841

Beds : 5

Lot Size : 135 Acres

Living Area Size : 5,203

Tax Amount : 52890.00

Year Built : 2020

Garage : 3

County : Columbia

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Feature Features

  • Bedroom Information

    Total beds: 5

    Bathroom Information

    Total Baths: 7 Full Baths: 6 Half Baths: 1

    Room Information

    Rooms Total: 20 Basement: Unfinished
  • Flooring Information

    Hardwood
  • Interior Features

    High Ceilings, Kitchen Island, Open Floorplan, Master Downstairs Appliances: Dishwasher, Dryer, Gas Range, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
  • Heating & Cooling

    Has Heating: Yes Heating: See Remarks Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 2020 Construction Materials: Wood Siding Pool Features: Private Private Pool: Yes Water front Features: Waterfront Access View: Lake, Mountain(s), Panoramic

  • Lot Information

    Lot Size Acres: 135 Lot Size Square Feet: 5880600

  • Listing Price Information

    Listing Price: $21000000

  • Tax Information

    Parcel Number: 104200-105-000-0001-004-003-0000 Annual Tax: $52890

  • Parking Information

    Driveway, Private

    Garage Information

    Has Garage: Yes Garage Space: 3

  • School Information

    Elementary School: Taconic Hills Elementary School
    Junior High School: Taconic Hills Junior/Senior High
    Senior High School: Taconic Hills Junior/Senior High
  • Utility Information

    See Remarks
  • Location Information

    WaterSource: Other
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
292 White Hill Rd, Hillsdale, NY, 12529 $2,195,000 3 3 2,755 21.50 Acres
292 White Hill Road, Hillsdale, NY, 12529 $2,195,000 3 3 2,755 21.50 Acres
417 Overlook Drive, Hillsdale, NY, 12529 $729,900 3 3 1,834 2.17 Acres
417 Overlook Drive, Hillsdale, NY, 12529 $729,900 3 3 2,210 2.07 Acres
309 Pine Ridge Lane, Hillsdale, NY, 12529 $900,000 3 3 2,495 6.27 Acres
124 Syre Lane, Hillsdale, NY, 12529 $3,300,000 4 3 5,760 12.02 Acres
25 Nobletown Rd, Hillsdale, NY, 12529 $999,000 4 3 1,344 300.80 Acres
25 Nobletown Road, Hillsdale, NY, 12529 $999,000 4 3 1,344 300.80 Acres
25 Nobletown Road, Hillsdale, NY, 12529 $999,000 4 3 1,344 300.80 Acres
2999 New York 23, Hillsdale, NY, 12529 $725,000 4 3 2,225 12.50 Acres

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. 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 deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

ByOwner last updated this listing 09/06/2026 @ 04:43

MLS: 1040841 LISTED BY: Jonathan Stein, Douglas Elliman Real Estate 914-232-3700 SOURCE: OneKey MLS

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