21 Schoolhouse Road, Hillsdale, NY 12529 (MLS# 20265125)

Current Price: $21,000,000

Original List Price: 21000000

List Price: $21,000,000

Status: Active

Listing Contract Date: 2026-09-03

Property Sub Type: Single Family Residence

Listing Agreement: Exclusive Right To Sell

Owner Name: Sh Ridge LLC

Occupant Type: Owner

Lease Considered YN: No

Bedrooms Total: 5

Bathrooms Total: 6

Bathrooms Full: 5

Bathrooms Half: 1

Above Grade Finished Area: 5203

Living Area: 5203

New Construction YN: No

Year Built: 2020

Garage YN: Yes

Attached Garage YN: No

Garage Spaces: 4

Lot Size Acres: 135

Basement YN: Yes

Fireplace YN: Yes

Fireplaces Total: 2

Sign On Property YN: No

List Price/SqFt: 4036.13

Public Remarks: 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.

Major Change Timestamp: 2026-09-03T23:00:10Z

Major Change Type: New Listing

Status Change Timestamp: 2026-09-03

Liber/Book: 961

Page: 922

Showing Attended YN: Yes

Showing Instructions: Contact Nikki @ 413-822-0200 or Jonathan @ 917-763-3514 for showings

Bathroom Level: First

Dining Room Level: First

Kitchen Level: First

Laundry Level: First

Library Level: First

Living Room Level: First

Primary Bedroom Level: First

Street Number: 21

Street Name: Schoolhouse

Street Suffix: Road

County: Columbia

State: NY

Zip Code: 12529

Town (Taxable): Hillsdale