$21,000,000
21 Schoolhouse Rd
Hillsdale, NY 12529
MLS# 250741
5 beds  |  6 baths  |  5203 sqft


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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.

Details
Maps
Contract Information
Current Price: $21,000,000
Status: Active
List Date: 2026-09-03
Accessory Dwelling Unit: No
List Price: $21,000,000
Original List Price: 21000000
Limited Service: No
Agent Interest: None
Location, Tax & Legal
Registry: Outside Berkshire New York
Street #: 21
Street Name: Schoolhouse
Street Ext: Rd
State/Province: NY
Postal Code: 12529
General Property Description
Realtor.COM Type: Residential - Single Family
Sq Ft Liv Apx: 5203
Sq Ft Source: Assessor
Total Rooms: 10
Total Bedrooms: 5
Total Full Baths: 5
Total Half Baths: 1
Total Bathrooms: 6
Parking Spaces Type: Garaged
Year Built Apx: 2020
Year Built Source: Assessor
Lot Size Dimensions: 135
Acres Apx: 135
Lot Size SqFt: 5880600
Building Info
Exterior Color: Grey
Status Change Info
Status Change Date: 2026-09-04
Property Features
Restrict Covenants: No
Title V: Not Applicable
Underground Oil Tank: No
Water: Well
Sewer: Private
Easement: Unk
Survey: Yes
Right of Way: No
Right to Farm Comm: Yes
Flood Hazard Area: No
Views: Distant; Hill/Mountain; Pastoral; Pond; Scenic; Water
Electric Type: 200 Amp
Style: Contemporary
Interior Amenities: Alarm System; Cathedral Ceilings; Fireplace (s); Hot Tub
Appliances Incl: Dishwasher; Dryer; Microwave; Range; Range Hood; Refrigerator; Washer
Construction: Wood Frame
Exterior Siding: Wood
Roof: Standing Seam Metal
Basement: Unfinished
Floor: Ceramic Tile; Wood
Garage: Detached; Heated; Insulated; Oversized
Fuel: Propane
Hot Water: Electric
Lead Paint: N/A, built 1978 or later
Zoning: Agricultural; Residential
Seller Disc: Yes
Possession: Close Of Escrow
Supplements
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.
Room Information
Room Name Level Remarks
KitchenFirst
Living RoomFirstWood Burning Fireplace
Dining RoomFirstOpen Concept
Primary BedroomFirst
Primary BedroomFirst
Primary BathroomFirst
Primary BathroomFirst
LibraryFirstWood Burning Fireplace
Bedroom 2First
Bedroom 3First
Bedroom 4First
Full BathroomFirstEnSuite
Full BathroomFirstEnSuite
Full BathroomFirstEnSuite
LaundryFirst
Half BathroomFirst
KitchenFirstGuest House
Living RoomFirstGuest House
Full BathroomFirstGuest House
Bedroom 1First

Listing Courtesy of STONE HOUSE PROPERTIES, LLC
Listing Agent: Nikki Carchedi

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