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21 Schoolhouse Road, 
Hillsdale, NY 12529

$21,000,000


5

Beds


6

Baths


5,203

Sq Ft


Single Family

Active

Listed by

Nikki Carchedi

Stone House Properties, LLC.

413-232-4253

Last updated:

October 18, 2026, 06:45 PM

MLS#

20265125

Source:

NY MLSUC

About This Home

21 Schoolhouse Road

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.

Home Facts

Single Family

6 Baths

5 Bedrooms

Built in 2020

Price Summary

21,000,000

$4,036 per Sq. Ft.

MLS #:

20265125

Last Updated:

October 18, 2026, 06:45 PM

Added:

1 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

6

Full Bathrooms:

5

Interior

Living Area:

5,203 Sq. Ft.


Structure

Structure

Architectural Style:

Contemporary

Building Area:

5,203 Sq. Ft.

Year Built:

2020


Lot

Lot Size (Sq. Ft):

5,880,600


Finances & Disclosures

Finances

Price:

$21,000,000

Price per Sq. Ft:

$4,036 per Sq. Ft.

Source:NY MLSUC
The information being provided by Hudson Valley Catskill Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Hudson Valley Catskill Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.