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The Frith Team
Licensed Real Estate Salespersons
Christine and Joseph Frith
(518) 928-9923
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21 Schoolhouse Road, Hillsdale, NY 12529

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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. 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.

21 Schoolhouse Road | MLS# 20265125

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 has 5 bedrooms and 5 full and 1 partial baths with 5203 sq. ft. Schoolhouse Road is located within the Taconic Hills Central Schools school district. Search Hillsdale real estate on thefrithteam.coldwellbankerprime.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Cooling: Central Air
Fireplaces: 2
Fuel Type: Propane
Garage: 4
Heating: Forced Air, Hot Water, Propane
Home Style: Contemporary
Lot Size: 135.00 Acres
Roof Type: Metal
Stories: 1.0
Taxes: $52,890

Amenities

High Speed Internet
Fire Pit
Lighting
Private Yard

Feature Descriptions

Appliances: Washer, Range Hood, Electric Water Heater, Dryer, Dishwasher, Built-In Refrigerator, Built-In Gas Range
Days on Site: 15
Exterior: Wood Siding
Fireplace: Library, Living Room
Flooring: Ceramic Tile, Wood
Laundry: Laundry Room
Lot: Agricultural, Cleared, Gentle Sloping, Landscaped, Many Trees, Pasture, Secluded, Views
Parcel #: 43
Patio/Porch: Patio
Pool: Gunite, In Ground, Infinity
Road Frontage: County Road
Road Surface: Gravel
Sewer: Septic Tank
SQFT Total: 5203
Swimming Pool: Yes

Local Schools

School District: Taconic Hills Central Schools

Estimate Your Payment

Estimated Payment

$ 57,269.40 per month $46,736.90 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)

Demographics

Listed By / Shown By

Listing By

Agency Name: Stone House Properties, LLC

Shown By

Agent Name: The Frith Team
Agent Phone: (518) 928-9923
Agency Title: Coldwell Banker Prime Properties

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information 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. Information on this site was last updated 09/19/2026. The listing information on this page last changed on 09/19/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 09/19/2026 12:04:23 AM EST) or Global MLS (last updated Fri 09/18/2026 11:52:31 PM EST) or New York State Alliance MLS (last updated Sat 09/19/2026 12:03:12 AM EST) or Hudson Valley Catskill Region MLS (last updated Sat 09/19/2026 12:01:14 AM EST) or Berkshire MLS (last updated Fri 09/18/2026 8:13:41 PM EST) or OneKey MLS (last updated Sat 09/19/2026 12:00:26 AM EST). Real estate listings held by brokerage firms other than Coldwell Banker Prime Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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