$21,000,000

21 Schoolhouse Rd, Hillsdale, NY 12529

Hillsdale, NY

Active
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5 Beds
5.50 Baths
5,203 Sq Ft
Residential Type

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.

Photos

Property Details

On Market Date 2026-09-04
Status Change Timestamp 2026-09-04T11:19:09Z
Elementary School Other
Major Change Type New Listing
Lot Size Units Acres
Documents Count 1
Listing Service No
Lot Size Square Feet 5880600
Middle Or Junior School Other
List Agent Office Phone 413-232-4253
Listing Id 250741
View YN 1
Year Built 2020
List Agent URL www.nikkicarchedi.com
List Agent Preferred Phone 413-822-0200
Longitude -73.55642
Source System Name Berkshire County Board of REALTORS®
Source System Key 20260903232310380551000000
Latitude 42.272101
Heating YN 1
Bathrooms Total Integer 6
List Office Fax 413-232-7718
State Or Province NY
Originating System Key 20260903232310380551000000
List Price 21000000
Photos Count 52
Other Parking Garaged
List Office URL http://www.stonehouseproperties.com/
List Agent State License 9089914
Photos Change Timestamp 2026-09-04T11:19:10Z
Building Area Total 5203
Lot Size Acres 135
Originating System Name Berkshire County Board of REALTORS®
Original List Price 21000000
Listing Contract Date 2026-09-03
Street Suffix Rd
Rooms Total 10
Originating System ID M00000305
Lot Size Dimensions 135
Street Number 21
Street Name Schoolhouse
List Agent Email [email protected]
Modification Timestamp 2026-09-04T14:53:38Z
List Office Mls Id 210
Postal Code 12529
Standard Status Active
City Hillsdale
High School Other
Mls Status Active
Lot Size Area 135
Source System ID M00000305
Zoning Description Agricultural, Residential
List Office Email [email protected]
List Agent Mls Id 2048
Documents Change Timestamp 2026-09-04T11:19:10Z
Tax Year 2026
Major Change Timestamp 2026-09-04T11:19:09Z
Living Area 5203
Year Built Source Assessor
Directions TSP to Harlemville Road. Left on County 21. Left on Schoolhouse Road Latitude: 42.270969 Longitude: -73.556476
MLSArea Major Outside Berkshire New York
Living Area Source Assessor
Days On Market 1
Unparsed Address 21 Schoolhouse Rd, Hillsdale, NY 12529
Listing Key 20260903232310380551000000
MLSArea Minor Outside Berkshire New York
List Office Phone 413-232-4253
Bathrooms Total Decimal 5.5
Approval Status 1
Originating System Platform ID T00000052
Originating System Platform Name Flexmls
Source System Platform ID T00000052
Source System Platform Name Flexmls
Property Type Residential
Contract Status Change Date 2026-09-04
Tax Annual Amount 52890
Bathrooms Full 5
Internet Consumer Comment YN 1
Internet Automated Valuation Display YN 1
Bedrooms Total 5
List Agent Key 20080112080729699491000000
Street Number Numeric 21
Internet Address Display YN 1
List Agent Mobile Phone 413-822-0200
Bathrooms Half 1
Internet Entire Listing Display YN 1
List Office Key 20080112080622207654000000
List Agent National Association Id 447501246
Existing Lease [email protected] None
Off Market [email protected] None
Buyer Team [email protected] None
List Team [email protected] None
New Construction [email protected] None
Number Of Separate Electric [email protected] None
Association Fee [email protected] None
Mobile [email protected] None
On Market [email protected] None
Cooling [email protected] None
Association [email protected] None
Copyright [email protected] None
List Team [email protected] None
Pets [email protected] None
Community [email protected] None
Association [email protected] None
Number Of Separate Water [email protected] None
Body [email protected] None
Buyer Team [email protected] None
Park [email protected] None
Mobile [email protected] None
Rent [email protected] None
Laundry [email protected] None
Videos Change [email protected] None
Virtual Tour [email protected] None
Entry [email protected] None
Garage [email protected] None
Lease [email protected] None
Number Of Units [email protected] None
Business [email protected] None
Property Sub [email protected] None
Waterfront [email protected] None
Building sp Info co Exterior sp Color Grey
Contract sp Information co Accessory sp Dwelling sp Unit No
Contract sp Information co Agent sp Interest None
General sp Property sp Description co Realtor COM sp Type Residential - Single Family
General sp Property sp Description co Total sp Bathrooms2 6

Nikki Carchedi

STONE HOUSE PROPERTIES, LLC

[email protected]

413-822-0200