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Susan Schefler
REALTOR®
(516) 244-6712
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21 Schoolhouse Road, Hillsdale, NY 12529

$21,000,000
  • 21 Schoolhouse Road, Hillsdale, NY 12529 Main Photo

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New to the Market Active
BEDS5 BATHS6 full 1 partial SQUARE FEET5,203 MLS#1040841
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLTaconic Hills

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 f

21 Schoolhouse Road | MLS# 1040841

This single family home located at 21 Schoolhouse Road, Hillsdale, NY 12529 is currently listed for sale with an asking price of $21,000,000. This property was built in 2020 and has 5 bedrooms and 6 full and 1 partial baths with 5203 sq. ft. Schoolhouse Road is located within the Taconic Hills school district. Search Hillsdale real estate on www.susanschefler.com today.

Property Features

Property Type: Residential - Single Family
Basement: Unfinished
Basement: Yes
Cooling: Central Air
Fireplaces: 2
Garage: 3
Heating: See Remarks
Home Style: Farmhouse, Modern, Other
Lot Size: 135.00 Acres
Taxes: $52,890
Year Built: 2020

Amenities

First Floor Bedroom
First Floor Full Bath
High Ceilings
Kitchen Island
Open Floorplan
Primary Bathroom
Master Downstairs

Feature Descriptions

Appliances: Dishwasher, Dryer, Gas Range, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Days on Site: 2
Exterior: Wood Siding
Fireplace Y/N: Yes
Flooring: Hardwood
GarageY/N: Yes
HorseY/N: Yes
On Market Date: 2026-09-03
Other Structures: Arena, Barn(s), Garage(s), Guest House
Parcel Number: 104200-105-000-0001-004-003-0000
Parking Features: Driveway, Private
Rental Term: Monthly
Rooms Total: 20
Sewer: Septic Tank
Special View Info: Lake, Mountain(s), Panoramic
Swimming Pool: Yes
Utilities: See Remarks
Water: Other

Local Schools

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

Estimate Your Payment

Estimated Payment

$ 116,719.93 per month $106,187.43 Principal & Interest $4,407.50 Property Tax $6,125.00 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Listed By / Shown By

Listing By

Agency Name: Douglas Elliman Real Estate
Agency Contact: 914-232-3700

agent picture

Shown By

Agent Name: Susan Schefler
Agent Phone: (516) 244-6712
Agency Title: Coldwell Banker American Homes

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