365 Tower Hill Rd
Description
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.
Listing Agent
![Ashley Whittaker]()
P: (917)-690-4567
Property Details for 365 Tower Hill Road
Property Details for 365 Tower Hill Road
| Status | Active |
|---|---|
| MLS # | 1002180 |
| Days on Market | 1 |
| Taxes | $82,600 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Single Family |
| Year Built | 2019 |
| Lot Size | 165.42 AC / 7,205,695 SF |
| County | Dutchess County |
Location
Building Information for 365 Tower Hill Road
Payment Calculator
$89,105 per month
30 year fixed, 6.36% Interest
$82,221
$6,883
$0
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1Property Information for 365 Tower Hill Road
- Senior Community YN: No
- 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.
- Property Attached: No
- Structure Type: Detached
- Levels: Three Or More
- State Or Province: NY
- Water Access YN: No
- School District: Webutuck (Northeast Central)
- Elementary School District: Webutuck (Northeast Central)
- Elementary School: Webutuck Elementary School
- Middle Or Junior School District: Webutuck (Northeast Central)
- Middle Or Junior School: Webutuck
- High School District: Webutuck (Northeast Central)
- High School: Webutuck High School
- Lease Considered: No
- Building Units Total: 1
- Parcel Number: 132000-7065-00-266271-0000
- Tax Assessed Value: $7,363,100.00
- Tax Source: Other
- Tax Year: 2025.0
- Association: No
- Amenities: Barn(s), Chefs Kitchen, Deck, Elevator, Entrance Foyer, Hardwood Floors As Seen, High Ceilings, His and Hers Closets, In Ground, Kitchen Island, Modern, Patio, Soaking Tub, Stable(s), Terrace, Walk In Closet, Washer/Dryer Hookup, Water Access, Well, Wet Bar, Wood Burning
- 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
- Appliances: Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Refrigerator, Washer
- Total Rooms: 11
- Basement: Partially Finished
- Attic Description: None
- Fireplace: Yes
- Fireplaces Total: 5
- Fireplace Features: Wood Burning
- Location Amenities: Hardwood Floors As Seen, Chef's Kitchen, Elevator, Entry Foyer, Foyer, High Ceilings, Island Kitchen, Soacking Tub, Walk In Closet, WD Hookup, Wetbar, Barn(s), Deck, Patio, Terrace, In Ground Pool, Water Access
- Spa: Yes
- Flooring: Hardwood
- Living Area: 7,500.00
- Basement: Yes
- Exterior Property Features: In Ground, Deck, Patio, Terrace, Driveway, Garage
- Elevation Certificate: Yes
- Patio And Porch Features: Deck, Patio, Terrace
- Construction Materials: Stucco, Wood Siding
- Other Structures: Barn(s), Stable(s)
- Waterfront Features: Water Access
- Pool Private: Yes
- Pool Features: In Ground
- Pool Details: In Ground
- Additional Parcel: No
- Building Area Units: Square Feet
- Parking Features: Driveway, Garage
- Garage: Yes
- Carport: No
- Cooling: Central Air
- Heating: Forced Air, Propane
- Heat Fuel Type: Forced Air, Propane
- Sewer: Septic Tank
- Water Source: Well
- Utilities: Electricity Connected, Phone Available, Phone Connected, Propane
- Green Features: Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Refrigerator, Washer, Forced Air, Propane, In Ground
- Down Payment Resource: No
Property History for 365 Tower Hill Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 22, 2026 | Listed (Active) ONEKEY #1002180 | $16,500,000 | — |
| Sep 6, 2024 | Expired ONEKEY #M418300 | $20,000,000 | — |
| Sep 6, 2024 | Expired ONEKEY #HM418300 | $20,000,000 | — |
| Sep 20, 2023 | Listed (Active) MHMLS #418300 | $25,000,000 | — |
| Sep 20, 2023 | Listed (Active) ONEKEY #HM418300 | $25,000,000 | — |
| Sep 20, 2023 | Listed (Active) ONEKEY #M418300 | $25,000,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/22/2026 | Listed (Active) ONEKEY #1002180 | $16,500,000 |
| 09/06/2024 | Expired ONEKEY #M418300 | $20,000,000 |
| 09/06/2024 | Expired ONEKEY #HM418300 | $20,000,000 |
| 09/20/2023 | Listed (Active) MHMLS #418300 | $25,000,000 |
| 09/20/2023 | Listed (Active) ONEKEY #HM418300 | $25,000,000 |
| 09/20/2023 | Listed (Active) ONEKEY #M418300 | $25,000,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Schools near 365 Tower Hill Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 3 | |||
| Public - | 4 to 8 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
Webutuck Elementary School PublicPK to 3 | ||
Eugene Brooks Middle School Public4 to 8 | ||
Webutuck High School Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Based on information submitted to the MLS GRID as of 05/22/2026 05:08 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively 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. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.
