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You are here: Home / 21 Schoolhouse Road, Hillsdale, NY 12529 (MLS # 1040841)

21 Schoolhouse Road, Hillsdale, NY 12529 (MLS # 1040841)

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Price $21,000,000
Status Active
Beds 5
Baths 6.5 Baths
Home size 5,203 sqft
Lot Size 135.00 ac
Days on Market 3
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.
Property Type(s): Single Family
Last Updated 9/3/2026 Year Built 2020
Garage Spaces 3.0 County Columbia

SCHOOLS

Elementary School Taconic Hills Elementary School
Jr. High School Taconic Hills Junior/Senior High
High School Taconic Hills Junior/Senior High

Additional Details

AIR Central Air
AIR CONDITIONING Yes
APPLIANCES Dishwasher, Dryer, Gas Range, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
BARN/EQUESTRIAN Yes
BASEMENT Unfinished
CONSTRUCTION Wood Siding
FIREPLACE Yes
GARAGE Yes
HEAT See Remarks
INTERIOR High Ceilings, Kitchen Island, Master Downstairs, Open Floorplan
LOT 135 acre(s)
PARKING Driveway, Private
POOL Yes
POOL DESCRIPTION Private
SEWER Septic Tank
STORIES 1
STYLE Farmhouse, Modern, Other
TAXES 52890
UTILITIES See Remarks
VIEW Yes
VIEW DESCRIPTION Lake, Mountain(s), Panoramic
WATER Other
WATERFRONT DESCRIPTION Waterfront Access

Location

 

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Listed with Douglas Elliman Real Estate
HGMLS logo Copyright 2026 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.
The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than Suburban Realty are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. Information deemed reliable but not guaranteed.
Date Last Updated: 9/6/26 3:25 AM PDT

This IDX solution is (c) Diverse Solutions 2026.

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About Janet

I have been a Realtor since 1982, and loving it. Serving Rockland County, New York, as well as Bergen County, New Jersey. I am with you every step of the way.

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Janet Eisenberg

Licensed Real Estate Broker in
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31 Drexel Court
New City, NY 10956

info@suburban-realty.com
Phone: (845) 425-3379
Cell: (914) 714-2004

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Janet Eisenberg – Broker at Suburban Realty Inc.

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