The downside to sorting listings out by simplified search filters like "single-family," "condo" and "co-op" is that the pleasant obscurities sometimes sift through the cracks. Here in our history-steeped suburbs north of New York City, one such study is the Gentleman's Farm, a vestige of pre-suburban suburbia when the transition from urban to rural was immensely more dramatic. Unlike the working variety, these farms were boutique operations, established by bourgeois landowners not to derive a livelihood but instead cultivate modest crops, raise thoroughbreds and furnish plain and simple solace. Those that weren't reborn as bed and breakfasts remain private homes, and with the ever-increasing popularity of locavore lifestyles and the farm-to-table movement, these unique properties are enjoying a modern renaissance here in the Hudson Valley and Southwest Connecticut. Here are just a handful currently on the market in our area:
SOUTH SALEM | 44 Boway Road | $4,950,000
Dating to 1756, Sassafras Farm is one of Westchester's finest historic properties currently on the market. The drive down Boway Road, an unpaved dirt street, is a trip back in time, soon revealing the 21-acre property with rights to nearby Lake Truesdale. The home abounds with character, complemented with charming outbuildings that include a guest house, stable and indoor riding ring, artist's studio and five-car garage. A rock pool, lighted tennis court and gorgeous gardens embellish the site's timeless draw.
PAWLING | 747 North Quaker Hill Road | $3,400,000
Atop Pawling's Quaker Hill, Beaver Pond Farm is an authentically restored colonial estate comprising 110 rolling acres of open meadows, natural woodlands, wandering trails and a large stocked pond. The five-bedroom main house, c. 1770 (with an addition in 1820), is perfectly sited to provide an idyllic overlook of the sprawling property, which includes a separate three-bedroom guest house, one-bedroom log home and myriad barns and outbuildings.
KATONAH | 270-306 Hook Road | $9,995,000
Wildflower Farm is a relative junior in juxtaposition. Centered around a nonagenarian gambrel-roofed stone-and-shingle residence, the 40-acre Bedford estate beckons with its 80-foot veranda, subtle beauty and bright mid-century studio addition. It's on the market for the first time in over 50 years, and if that fireplace yours, we wouldn't hold it against you for staying put just as long.
CORTLANDT MANOR | 91-99 Watch Hill Road | $4,999,000
Hotelier Claude Philippe, the legendary Waldorf-Astoria banquets manager famously fired for booking Harry Belafonte in 1959, hosted countless celebrities during his time owning this fetching farm, where he retreated when not expanding the Loews hotel empire or building a golf course in Guadeloupe. (We're not sure who was on his guest list, but Grace Kelly, Barbara Walters and Marilyn Monroe are all likely suspects). The 13+ acre property includes a handsome 18th century farmhouse, large carriage house, ice house and a barn converted for living purposes.
BREWSTER | 310 Dingle Ridge Road | $4,500,000
Naval Commander Edward E. Spafford built this pristine 17-acre estate in the 1920s, with a five-bedroom, seven-bath stone Tudor manor that was masterfully restored and expanded in 2007. A special highlight is the pool and a stellar pool house, which includes a full kitchen, outdoor shower and complementing pergola. A carriage house and caretaker's apartment, greenhouse and tennis court are also on the grounds, and its site within the the North Salem Bridle Trails Association makes horses, paddocks and riding rings an easy addition.