21 Schoolhouse Rd, Hillsdale, NY 12529 (MLS# 250741)
21 Schoolhouse Rd
Hillsdale, NY 12529
MLS# 250741
5 beds | 6 baths | 5203 sqft
Property DescriptionThere 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.
Accessory Dwelling Unit: No
Original List Price: 21000000
Limited Service: No
Agent Interest: None
Current Price: $21,000,000
Status: Active
List Date: 2026-09-03
List Price: $21,000,000
Elem School: Other
Middle School: Other
High School: Other
Taxes: 52890
Tax Year: 2026
Registry: Outside Berkshire New York
Street #: 21
Street Name: Schoolhouse
Street Ext: Rd
State/Province: NY
Realtor.COM Type: Residential - Single Family
Total Bathrooms: 6
Parking Spaces Type: Garaged
Sq Ft Source: Assessor
Total Rooms: 10
Total Bedrooms: 5
Year Built Source: Assessor
Lot Size Dimensions: 135
Lot Size SqFt: 5880600
Sq Ft Liv Apx: 5203
Total Full Baths: 5
Total Half Baths: 1
Year Built Apx: 2020
Acres Apx: 135
Directions: TSP to Harlemville Road. Left on County 21. Left on Schoolhouse Road
Latitude: 42.270969 Longitude: -73.556476
Range Hood: 1
Refrigerator: 1
Central AC: 1
Forced Air: 1
Alarm System: 1
Cathedral Ceilings: 1
Fireplace (s): 1
Hot Tub: 1
N/A, built 1978 or later: 1
Distant: 1
Hill/Mountain: 1
Agricultural: 1
Residential: 1
Status Change Date: 2026-09-04
Views: Distant; Hill/Mountain; Pastoral; Pond; Scenic; Water
Interior Amenities: Alarm System; Cathedral Ceilings; Fireplace (s); Hot Tub
Appliances Incl: Dishwasher; Dryer; Microwave; Range; Range Hood; Refrigerator; Washer
Roof: Standing Seam Metal
Floor: Ceramic Tile; Wood
Garage: Detached; Heated; Insulated; Oversized
Lead Paint: N/A, built 1978 or later
Zoning: Agricultural; Residential
Possession: Close Of Escrow
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 Name | Level | Remarks |
| Kitchen | First | |
| Living Room | First | Wood Burning Fireplace |
| Dining Room | First | Open Concept |
| Primary Bedroom | First | |
| Primary Bedroom | First | |
| Primary Bathroom | First | |
| Primary Bathroom | First | |
| Library | First | Wood Burning Fireplace |
| Bedroom 2 | First | |
| Bedroom 3 | First | |
| Bedroom 4 | First | |
| Full Bathroom | First | EnSuite |
| Full Bathroom | First | EnSuite |
| Full Bathroom | First | EnSuite |
| Laundry | First | |
| Half Bathroom | First | |
| Kitchen | First | Guest House |
| Living Room | First | Guest House |
| Full Bathroom | First | Guest House |
| Bedroom 1 | First | |
Listing Courtesy of STONE HOUSE PROPERTIES, LLC
Listing Agent: Nikki Carchedi
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