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21 Schoolhouse Road

Hillsdale, NY 12529
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Bed 5

Bed

Bath 6

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 kit chen 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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Detail Ic Property Details

Property Type : Residential

Price : $21,000,000

AD Id : 91004237

MLS Id : 20265125

Beds : 5

Lot Size : 135 Acres

Living Area Size : 5,203

Tax Amount : 52890.00

Year Built : 2020

Garage : 4

County : Columbia

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Feature Features

  • Bedroom Information

    Total beds: 5

    Bathroom Information

    Total Baths: 6 Full Baths: 5 Half Baths: 1

    Room Information

    Has Basement: Yes Basement: Unfinished
  • Flooring Information

    Ceramic Tile, Wood
  • Roofing Information

    Metal
  • Interior Features

    High Speed Internet, Master Downstairs Roof: Metal Appliances: Built-In Gas Range, Built-In Refrigerator, Dryer, Dishwasher, Electric Water Heater, Range Hood, Washer Laundry Features: Laundry Room
  • Heating & Cooling

    Has Heating: Yes Heating: Forced Air, Hot Water, Propane Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 2020 Building Area Total: 5203 Construction Materials: Wood Siding Patio And Porch Features: Patio Pool Features: Gunite, In Ground, Infinity Private Pool: No View: Pond, Panoramic, Pool, Pasture, Ridge, Skyline
  • Exterior Features

    Exterior Features: Fire Pit, Lighting, Private Yard

  • Lot Information

    Main Square Feet: 135 Acres Lot Size Acres: 135 Lot Size Square Feet: 5880600 Lot Description: Sloped, Agricultural, Cleared, Gentle Sloping, Landscaped, Many Trees, Pasture, Secluded, Views

  • Listing Price Information

    Listing Price: $21000000

  • Tax Information

    Parcel Number: 43 Tax Lot: 105 Tax Block: 1 Annual Tax: $52890 Tax Legal Desc: Residential

  • Garage Information

    Has Garage: Yes Garage Space: 4
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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 (IDX) program of the Ulster County Board of REALTORS®. 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 Ulster County Board of REALTORS®, Inc.

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

MLS: 20265125 LISTED BY: Nikki Carchedi, Stone House Properties, LLC SOURCE: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS)

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