365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
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365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
365 Tower Hill Road
Courtesy of Compass Greater NY, LLC, Ashley Whittaker Spence Listing Contact:  
For Sale

365 Tower Hill Road

365 Tower Hill Road, Wassaic, NY 12592

$16,500,000
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.

4
beds

8
baths

7,500 Sq.Ft. LIVING AREA

165.42 Acres lot

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Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.
Thank you for your interest in 365 Tower Hill Road, Wassaic, NY 12592. We are reviewing your request and will be in touch shortly!
Ashley Whittaker Spence

Ashley Whittaker Spence

Features & Amenities

Interior

  • total bedrooms4
  • Total bathrooms8
  • full bathrooms5
  • half bathrooms3
  • Flooring Hardwood
  • Fireplace Wood Burning
  • APPLIANCES Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Refrigerator, Washer
  • other 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

Area & Lot

  • Status For Sale
  • Living Area7,500 Sq.Ft.
  • Total Area11,250 Sq.Ft.
  • Lot Area165.42 Acres
  • MLS® ID1002180
  • TypeResidential
  • YEAR BUILT2019
  • Architecture StylesModern
  • Water FrontageWater Access
  • Elementary SchoolWebutuck Elementary School
  • Middle SchoolWebutuck
  • High SchoolWebutuck High School
  • School DistrictWebutuck (Northeast Central)

Exterior

  • STORIES3
  • Garage Space3.0
  • water SourceWell
  • utilitiesElectricity Connected, Phone Available, Phone Connected, Propane
  • PoolIn Ground
  • parkingDriveway, Garage
  • HEAT TYPEForced Air, Propane
  • AIR CONDITIONINGCentral Air
  • sewerSeptic Tank

Financial

  • Sales Price$16,500,000
  • Real Estate Tax $82,600/yr

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Work With Us

Hudson Valley Team at Compass continues to represent with utmost discretion some of the world’s highest-profile personalities from top levels of government, finance, business, and entertainment, who seek the firm’s professional execution in the sales of country homes, historic and classic estates, and premier land to local, national and international buyers.

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