The Upside Down House, designed by Adam Rolston of INC Architecture and Design.
Set on 3 acres along one of Columbia County's most desirable roads, just minutes to downtown Great Barrington and the City of Hudson, NY.
Surrounded by hayfields with distant views, this super-energy efficient home features a 40-foot saltwater lap pool, outdoor shower, spring-fed pond, heated tile floors, steam shower, soaking tub and fiber internet.
Inspired by 18th-century, Swiss-style barns, with sleek black vertical stained cedar siding, the house fits seamlessly with the natural surroundings. Oversize German tilt-and-turn windows maximize the property's natural light and give the feeling of being in a tree house. The interior is white and fresh with expansive vaulted ceilings. Dining, living and kitchen occupy the upper floor, with three bedrooms and a large bathroom with walk-in steam shower on the lower level. Premium state-of-the-art designer kitchen with custom cabinetry and marble counters. A wood-burning fireplace in the living room makes the space cozy apres ski at nearby Catamount. A polished cement slab terrace leads to a 40' salt lap pool edged with bluestone and an outdoor shower.
Located in the estate section of Hillsdale NY, on Overlook Drive, the property is a 10-minute drive to downtown Great Barrington and 5 minutes to Catamount Ski Area, 30 min to the train in Hudson and 30 min to Tanglewood. A stunning spot from which to enjoy the best of what the Hudson Valley and Berkshires have to offer!
Sold for $1,220,000 on 06/24/25
$1,220,000
90 Overlook Dr, Hillsdale, NY 12529
3beds
2,100sqft
Single Family Residence
Built in 2014
3.1 Acres Lot
$1,248,200 Zestimate®
$581/sqft
$5,257 Estimated rent
What's special
Zillow last checked: 7 hours ago
Listing updated: June 30, 2025 at 07:45am
Listed by:
Jen Harvey 413-446-8489,
COMPASS MASSACHUSETTS , LLC GB
Bought with:
Non Member
NON-MEMBER / RECIPROCAL
Source: BCMLS,MLS#: 246333

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Electric, Radiant
Appliances
- Included: Dishwasher, Dryer, Range, Refrigerator, Washer
Features
- High Speed Wiring, Marble Counter, Steam Shower, Vaulted Ceiling(s)
- Flooring: Ceramic Tile, Wood
- Windows: Insulated Windows
- Basement: Other
Interior area
- Total structure area: 2,100
- Total interior livable area: 2,100 sqft
Property
Parking
- Parking features: Off Street
- Details: Off Street
Accessibility
- Accessibility features: Accessible Bedroom, Accessible Full Bath
Features
- Patio & porch: Patio
- Exterior features: Landscaped
- Has private pool: Yes
- Pool features: In Ground
- Has view: Yes
- View description: Pond, Pasture, Hill/Mountain
- Has water view: Yes
- Water view: Pond
- Waterfront features: Pond
Lot
- Size: 3.10 Acres
Details
- Additional structures: Outbuilding
- Parcel number: 10420012629
- Zoning description: Residential
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Roof: Metal
Condition
- Year built: 2014
Utilities & green energy
- Electric: 200 Amp, Circuit Breakers
- Sewer: Private Sewer
- Water: Well
- Utilities for property: Fiber Optic Availabl, Trash Private
Community & neighborhood
Location
- Region: Hillsdale