Pine Plains, NY homes for sale & real estate

Pine Plains, NY Homes for Sale

Modern Minimalist Masterpiece on 19 Bucolic Acres in Dutchess County. Welcome to a rare offering in the heart of the Hudson Valley, where striking modern architecture meets timeless pastoral beauty. Completed in late 2024, this extraordinary estate sits on over 19 acres of flat, fenced farmland at the picturesque intersection of Bethel Cross and Carpenter Hill Road. Perfectly sited on a south-facing rise along the Shekomeko Creek, this newly constructed home is a serene, sophisticated sanctuary just two hours from New York City. A bold fusion of modern, industrial, and eclectic design, the residence offers over 4,700 square feet of light-filled, open-concept living on one level, including 3

Pine Plains, NY Homes for Sale

Welcome to 37 Stissing Mountain Drive. Perfectly nestled on 6.9 acres of peaceful woodland, this newly built 2-bedroom, 2-bath home is a modern sanctuary that beautifully balances simplicity, sustainability, and style—just minutes from the heart of Pine Plains NY. Inside you will find a sun-filled, open-concept living space with soaring 22-foot vaulted ceilings that frame sweeping views of the surrounding forest. Clean architectural lines and radiant heat throughout the polished concrete floors create a warm, minimalist backdrop that’s both inviting and efficient year-round. Complete with a first floor bedroom and bath, home office space, and a generous lofted primary you have p

Pine Plains, NY Homes for Sale

Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an office, and a full bathroom off the hallway. There is also a walk up attic. Off the rear of the house, there is a workshop and several period barns. The property consists of two parcels; the house and barns on 10 acres plus an additional contiguous 5 acre vacant parcel. The land is lovely, with rolling hil

Pine Plains, NY Homes for Sale

First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation, the property offers spectacular panoramic views of the Catskills and Taconic Hills from sunrise to sunset. With hand-hewn luxury reminiscent of Ralph Lauren’s aesthetic, the log-and-stone main residence features wraparound porches, a great room with a dramatic stone fireplace, a chef’s e