A newly renovated main residence, with preservation of historic design details and hand-selected modern touches.
A shingle-style guest residence built in 1915, conveniently connected to the main house by a colonnaded pergola.
A luxurious minimalist space for entertaining and hosting guests, newly constructed in 2018.
An unparalleled country estate with a storied past and outstanding pedigree one hour from NYC. Renovated to the highest standards of modern esthetics, Whippoorwill Farm spans over 80 acres in the exclusive enclave of Garrison—home to many grand estates of the Gilded Age. Once the serene retreat of Vanderbilts and Osborns, and host to luminaries like Eleanor Roosevelt, this distinguished gentleman’s farm is tailored for the discerning buyer seeking premier quality, enduring charm, and ample space for extended family and friends to work, play, and unwind.
At its heart are three striking, fully renovated structures: a historic 19th-century home, a 1915 3-bedroom residence, and a 4-bedroom Guest Barn built in 2018.
Together these three buildings offer 12 bedrooms and 9.5 baths. The uncommon pastoral setting encompasses a newly surfaced tennis court, updated 48’ pool with an oversized stand-alone spa, enchanting stone walls, decorative apple grove, canoe-able private lake, and 3½ miles of manicured hiking trails. Helicopters easily land on the rear lawn.
Re-imagined and expanded for today’s casual living, the sophisticated Colonial Farmhouse—the main residence—has preserved key historic design details including a central staircase, several marble fireplaces, and ultra-wide board floors, including dark wood inlay. A modern renovation added an expansive sun-drenched great room off the front hall, framed by a view of the estate’s rolling hills, and enlarged the kitchen—anchored by a marble island—that encompasses a family room with cozy fireplace, breakfast area, and top-tier Thermador & Sub-Zero appliances. An original dining room with elegant carved mantel fireplace and updated vintage lighting is ideal for hosting.
With the quiet luxury of a private Englishman’s club, the richly lacquered study—complete with big windows, original fireplace, and wood-paneled walk-in bar—becomes a favorite gathering space. Conveniently, it’s steps from an impressive, light-filled home office.
Upstairs, a handsome primary suite offers a serene sanctuary with ample closets and walk-in wardrobes, and a destination spa bathroom with steam shower and cedar sauna.
Connected via a timeless colonnaded pergola is the shingle-style Guest House. With three well-appointed bedrooms, an outstanding billiards room paneled in Idaho pine, a sunny kitchen with Bosch appliances, and a spectacular glass-walled workout room that can easily flex as a bedroom.
Luxurious minimalism with natural materials, neutral colors, and exposed beams defines the breathtaking Guest Barn, constructed in 2018 to provide a soothing, inviting space for friends and extended family.
Beyond the property’s private tranquility, Whippoorwill Farm benefits from proximity to a wealth of wonderful cultural and natural treasures. Treat yourself to the annual Hudson Valley Shakespeare Festival, Bear Mountain State Park, and the Garrison Institute spiritual retreat venue, as well as world-renowned art venues DIA Beacon and Storm King.
Local culinary gems include The Garrison, Dolly’s, the 18th-century Bird & Bottle Inn, and Le Bouchon in neighboring Cold Spring. Notably, the hamlet of Garrison is a part of Philipstown, where more than half of the land is protected from development through private and public land trusts. Just one hour to Manhattan.
