161 Whalesback Rd

Don’t miss this rare opportunity to own a breathtaking, fully renovated 5,500 sq ft converted barn in the heart of the Hudson Valley. Nestled on 15 private, picturesque acres in the safety and tranquility of Red Hook, NY, this extraordinary 5-bedroom, 4.5-bathroom home seamlessly blends historic charm with modern luxury.
Originally built in 1900, the barn has been thoughtfully transformed to preserve its character—soaring ceilings, exposed beams, and expansive open spaces—while offering every contemporary convenience. The home features a gracious open floor plan, oversized rooms, and a stunning in-ground pool with a flagstone patio, perfect for entertaining or peaceful country living.
Designed for both relaxation and productivity, the home also includes plenty of room for an office, a spacious game/family room, gym, studio, or guest space. Whether you're working remotely, hosting family and friends, or simply unwinding, this home offers space for every lifestyle.
Set in the center of equestrian country, this location offers unrivaled access to world-class destinations including Mashomack Preserve Club, Tamarack Preserve, and several notable new clubs emerging in the area. Families will appreciate proximity to top-tier public and private schools, a variety of excellent children’s camps, and some of the best skiing in the region. The vibrant local culture is further enriched by nearby Bard and Vassar Colleges, bringing world-class arts and events to your doorstep.
Conveniently located just minutes from the charming villages of Red Hook and Rhinebeck, 20 minutes to Hudson and Pine Plains, 30 minutes to Millbrook, and less than an hour to the Berkshires. You're also just 10 minutes from the Amtrak station with direct service to NYC, and under two hours away by car.
This is more than a home—it’s a lifestyle.