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.

Features
Heating System:
See Remarks
Cooling System:
Central Air
Basement:
Unfinished
View:
Lake, Mountain(s), Panoramic
Appliances:
Dishwasher, Oven, Refrigerator, Stainless Steel Appliance(s), Dryer, Washer, Range, Gas Range
Fireplaces Total:
2
Flooring:
Hardwood
Garage Spaces:
3
Interior Features:
Master Downstairs, Open Floorplan, High Ceilings, Kitchen Island, First Floor Bedroom, Primary Bathroom, First Floor Full Bath
Parking Features:
Driveway, Private
Sewer:
Septic Tank
Utilities:
See Remarks
Address Map
City:
Hillsdale
State:
NY
Street:
Schoolhouse
Street Number:
21
Street Suffix:
Road
Postal Code:
12529
Floor Number:
0
Longitude:
W74° 26' 45.1''
Latitude:
N42° 16' 2.6''
PostalCity:
Hillsdale
Additional Information
Architectural Style:
Other, Farmhouse, Modern
Construction Materials:
Wood Siding
Elementary School:
Taconic Hills Elementary School
High School:
Taconic Hills Junior/Senior High
Levels:
One
Agent MlsId:
346117
MiddleOrJunior School:
Taconic Hills Junior/Senior High
PhotosCount:
49
Special Listing Conditions:
No
Tax Annual Amount:
$52,890
Water Source:
Other
Office MlsId:
DOUGEL03

Residential - MLS# 1040841

21 Schoolhouse Road, Hillsdale, NY

5 Bedrooms
6 Bathrooms
5,203 Sqft
$21,000,000
Listing ID #1040841
Basic Details
Property Type :
Residential
Property SubType :
Single Family Residence
Listing Type :
For Rent
Listing ID :
1040841
Price :
$21,000,000
Rooms :
20
Bedrooms :
5
Bathrooms :
6
Half Bathrooms :
1
Bathrooms Total :
7
Square Footage :
5,203 Sqft
Lot Area :
135 Acre
Year Built :
2020
Status :
Active
Listing Agent :
Jonathan R. Stein
Listing Office :
Douglas Elliman Real Estate
Agent info
Coldwell Banker American Homes
284 West Park Ave
Contact Agent
Walkscore