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$16,500,000
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Property Description
Introducing Sky House. This 7,500-square-foot modern estate atop 138 acres of meadows, woodland, and rolling hills in Millbrook's storied hunt country is a study in serenity and design intelligence. Conceived by the celebrated firm Resolution: 4 Architecture and completed in 2019, the residence rises from the landscape with a long, linear silhouette tempered by floor-to-ceiling glass that invites the outdoors into its interior vocabulary. Here, architecture does not compete with nature; it offers a refined frame through which the Hudson Valley unfolds. A long private drive reveals the home as a subtle, sculptural form set against a panorama of the valley. The approach is intentionally understated; a cinematic progression culminating in the soaring glass foyer at the center of the home. The first floor unfolds as a sequence of generous, light-filled spaces, beginning with a great room defined by a dramatic blackened-steel fireplace surround and a monumental 20-foot retractable wall of glass that allows the room to open completely to the landscape beyond. Outside, an expansive covered terrace unfolds beneath a contemporary pergola, where shifting light and shadow animate the space throughout the day. Conceived as a true outdoor living room, the terrace offers multiple seating areas oriented toward panoramic views of the surrounding fields and distant mountains. Beyond lies a media room with its own fireplace, a handsome retreat for film, music, or winter nights. Just beyond, the office appears as a hushed sanctuary bathed in soft natural light. With views stretching across the landscape, it offers a beautiful connection to the world outside. The home features a chef's kitchen with contemporary millwork, discreet storage, and professional-grade appliances. Adjacent are a pantry, mudroom, powder room, and back-of-house spaces designed to support both intimate daily living and large-scale entertaining. A staircase of clean lines and floating geometry leads to the second level, though an elevator links all floors with ease. At the top, a spectacular outdoor terrace extends the living space into the sky. With lounge seating arranged around a sleek outdoor fireplace, it becomes a natural stage for twilight cocktails, summer dinners, and stargazing. The primary suite occupies its own wing, conceived as a restorative retreat. The bedroom, wrapped in glass and soft morning light, is complemented by dual dressing rooms, a massage and treatment room with fireplace, and a spa-inspired bath anchored by a sculptural soaking tub positioned toward the horizon. Separate indoor and outdoor showers offer a choice between privacy and open-air immersion. Three additional en suite bedrooms provide comfort and independence for guests, each with its own view and sense of calm. The outdoor amenities are equally sophisticated. A pool house with kitchen and lounge stands beside an infinity-edge pool and spa that appear to slip toward the valley below. A three-car garage, designed with the same architectural restraint as the main residence, adds practicality without compromising aesthetic integrity. Beyond the immediate grounds stretch acres of meadows, forested trails, and open fields suited for riding or walking. Though utterly private, the property is minutes from Millbrook's charming village center, local farmstands, dining, and regional hiking and riding trails. Yet its true allure lies in the equilibrium it creates between monumental design and whisper-soft landscape, between contemporary precision and the timeless calm of country life. More than a residence, Sky House is a living composition of light, terrain, and modern craft; a place for contemplative mornings, lively weekends, and the rare sensation of inhabiting a home that is simultaneously shelter, sculpture, and sanctuary.
Full Property Details
Full Property Details for 365 Tower Hill Rd
General
- Price: $16,500,000
- Taxes: $82,600
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 1002180
- Updated: 5/22/2026
- Added to Site: 8 day(s) ago
Interior
- Number of Rooms: 11
- Interior Features: Chefs Kitchen, Elevator, Entrance Foyer, High Ceilings, His and Hers Closets, Kitchen Island, Soaking Tub, Walk-In Closet(s), Washer/Dryer Hookup, Wet Bar
- Fireplace: Yes
- Number of Fireplaces: 5
- Fireplace(s): Wood Burning
- Appliances: Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Refrigerator, Washer
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 8
- Full Bathrooms: 5
- Half Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: In-Ground
- Spa: Yes
Exterior
- Porch/Patio/Deck: Deck, Patio, Terrace
Parking
- Garage: Yes
- Garage Spaces: 3
- Parking Features: Driveway, Garage
Location
- County: Dutchess County
- Driving Directions: Waze and/or Google Maps may take you to the wrong entrance on the property. Make sure you see the address marker (365) at the bottom of the driveway. You will see a modern steel automatic gate at the entrance.
School Information
- High School District: Webutuck (Northeast Central)
- Elementary School: Webutuck Elementary School
- Middle School: Webutuck
- High School: Webutuck High School
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Forced Air, Propane
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: Electricity Connected, Phone Available, Phone Connected, Propane
Structural Information
- Architectural Style: Modern
- Detached/Attached: Detached
- Construction: Stucco, Wood Siding
- Basement: Yes
- Basement Desc.: Partially Finished
- Building Size: 11250
- Square Feet: 11,250
- Sq. Ft. Source: Plans
- Year Built: 2019
Additional Structures
- Other Structures: Barn(s), Stable(s)
Lot Features
- Lot Size (Acres): 138.42
- Lot Size (Sq. Ft.): 7,205,695
Water Features
- Water Front View: Water Access
Financial Considerations
- Tax Amount: $82,600
Disclosures and Reports
- Special Conditions: None
- Property ID: 132000-7065-00-266271-0000
Listed by Compass Greater NY, LLC
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Schools
Schools serving 365 Tower Hill Rd
School District:Northeast Central School District
| Name | Grades | Distance |
|---|---|---|
Eugene Brooks Middle School 194 Haight Road, Amenia, NY 12501 | 5-8 | 7.4 mi |
Webutuck Elementary School 175 Haight Road, Amenia, NY 12501 | PK-4 | 7.5 mi |
Webutuck High School 194 Haight Road, Amenia, NY 12501 | 9-12 | 7.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 365 Tower Hill Rd
Date
Details
Price
Change
Source
5/22/2026
Listed
$16,500,000
371.43%
MLS
2/20/2014
Sold
$3,500,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 365 Tower Hill Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$91,888
-16%
$6,363,100
-14%
2024
$108,792
49%
$7,363,100
2%
2020
$72,964
—
$7,218,700
8%
2020
$72,964
158%
$6,684,000
69%
2021
$28,315
-61%
$3,947,000
—
2020
$72,964
36%
$3,947,000
—
2018
$53,847
-31%
$3,947,000
—
2017
$77,660
29%
$3,947,000
33%
2016
$60,035
53%
$2,976,800
—
2015
$39,117
40%
$2,976,800
—
2015
$27,881
2%
$2,976,800
—
2013
$27,414
—
$2,976,800
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 365 Tower Hill Rd
365 Tower Hill Road, Wassaic, NY 12592 (MLS# 1002180) is a Single Family property with 4 bedrooms, 5 full bathrooms and 3 partial bathrooms. 365 Tower Hill Road is currently listed for $16,500,000 and was received on May 22, 2026. Want to learn more about 365 Tower Hill Road? Do you have questions about finding other Single Family real estate for sale in Wassaic? You can browse all Wassaic real estate or contact a Coldwell Banker agent to request more information.
