21 Schoolhouse Road

Hillsdale, NY
$ 21,000,000 Beds 5 Baths 6.5 Sq 5,203
Monthly Estimate* How much can I afford?

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.

Single Family

  • Price
  • $ 21,000,000
  • City
  • Hillsdale
  • Bedrooms
  • 5
  • Full Bathrooms
  • 6
  • County
  • COLUMBIA
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 135 Acres
  • Zip
  • 12529
  • Sqr Footage
  • 5,203
  • Year Built
  • 2020
  • Taxes
  • $ 52890
  • Style
  • Farmhouse,Modern
  • MLS#
  • 1040841
Listed By: Douglas Elliman Real Estate
Data Source: Listings courtesy of OneKey® MLS as distributed by MLS GRID

Features

General

Sewer Septic Tank
Heating See Remarks
Cooling Central Air
Utilities See Remarks
Appliances Dishwasher,Dryer,Gas Range,Oven,Range,Refrigerator,Stainless Steel Appliance(s),Washer
Garage Spaces 3
Architectural Style Farmhouse,Modern,Other
Construction Materials Wood Siding
Year Built 2020
View Lake,Mountain(s),Panoramic
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 104200-105-000-0001-004-003-0000
County Columbia County
Property Type Residential
HOA No
Garage Y/N Yes
Other Structures Arena,Barn(s),Garage(s),Guest House
Total Rooms 20
Full Baths 6
High School Taconic Hills Junior/Senior High
City Hillsdale
Senior Community Y/N No
High School District Taconic Hills
Carport Y/N No
Elementary School Taconic Hills Elementary School
Property Attached Y/N No
Tax Annual Amount 52890
Middle/Junior High School Taconic Hills Junior/Senior High
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Taconic Hills
Elementary School District Taconic Hills
Tax Assessed Value 2878700
PostalCity Hillsdale
AttributionContact 914-232-3700
Listing Appliances Dishwasher, Dryer, Gas Range, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer

Interior Features

Interior Amenities First Floor Bedroom,First Floor Full Bath,High Ceilings,Kitchen Island,Open Floorplan,Primary Bathroom,Master Downstairs
Basement Unfinished
Flooring Hardwood
Total Fireplaces 2
Basement Features Unfinished
Basement (Y/N) Yes
Fireplace Y/N Yes
Half Baths 1
Total Bedrooms 5
Total Baths 7
General Features First Floor Bedroom,First Floor Full Bath,High Ceilings,Kitchen Island,Open Floorplan,Primary Bathroom,Master Downstairs

Exterior Features

Parking Features Driveway,Private
Water Source Other
Parking Features Driveway, Private
Waterfront Y/N No
Horse Y/N Yes

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Bay Shore, NY office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Taconic Hills Elementary School
Middle School Taconic Hills Junior/Senior High
High School Taconic Hills Junior/Senior High

Price History

9/4/2026 Listed $21,000,000

Property vs Zip Code Average in 12529

Price
AVG $690K
$21M
Taxes
AVG $6,343
$52,890
Year Built
AVG 1958
2020

Areas That We Cover

21 Schoolhouse Road Hillsdale, NY is a Single Family Home for sale at $21000000 with 5203 sqft and a lot size of 135 Acres Acre(s). 21 Schoolhouse Road Hillsdale has 5 bedrooms, 6 baths and was built in 2020. The property's zip code is 12529 which is in Hillsdale, NY

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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