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Windswept Farm - A Premier Catskills Estate Near Windham Mountain Club. Windswept Farm offers the perfect Upstate New York retreat just 4.6 miles from the Windham Mountain Club, 5.2 miles from Christman's Windham House Golf Club, and less than 2.5 hours from NYC. This postcard-perfect estate spans 113 acres at 351 N Settlement Road, with the option to purchase an additional contiguous 34.33 acres at 447 N Settlement Road, creating nearly 150 acres of extraordinary mountain-view countryside. Set against a backdrop of rolling hills, streams, and open meadows, Windswept Farm is ideal for buyers seeking a luxury second home, vacation property, or unique event venue within minutes of Windham's vibrant town center. With plenty of road frontage, it offers unmatched presence and accessibility. The renovated farmhouse showcases timeless elegance and modern comfort. Every detail—from the reclaimed Australian cypress, oak, and cherry wood floors to the luxury Waterworks and Ettoule finishes—reflects sophisticated craftsmanship. The home features four bedrooms, three with their own private en-suite bathrooms, offering exceptional comfort for guests. A spacious custom kitchen opens to a bluestone patio that welcomes outdoor entertaining, while the large mudroom with French doors and built-ins provides both style and function. With 5,050 finished square feet (including the heated lower level with a family room and den), there's room to live and gather in luxury. The property includes a three-car detached garage/ carriage house with a finished second floor, easily convertible into a guest house or caretaker's quarters, plus a cow barn, and pristine natural features such as a wide trout stream and picturesque pond. Whether you envision a private equestrian estate, a mountain getaway, or want to explore the possibility of creating an event space, Windswept Farm offers unmatched beauty, flexibility, and convenient proximity to all that Windham has to offer. Property Highlights: 113-acre estate with the option to purchase contiguous 34.33-acre parcel, 4 bedrooms, 3 en-suite baths, 5,050 sq. ft. finished living space, 4.6 miles to Windham Mountain Club and 5.2 miles to Christman's Golf Course, 3-car detached garage/carriage house with finished loft (ideal guest house conversion), Stream, pond, barns, bluestone patio, and mountain views. Less than 2.5 hours from New York City Experience Windswept Farm—your gateway to the luxury, tranquility, and timeless beauty of the Catskills. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
The Upstate Lifestyle at 351 North Settlement Road, Windham NY
Living here means you're positioned perfectly between mountain adventure and small-town charm. Windham Mountain Club sits less than two miles away, offering year-round recreation from winter skiing on 54 trails to summer golf and mountain biking—ideal for families who crave outdoor activity without the long drive. When you're ready for a more leisurely pace, the Windham Path's gentle 1.5-mile loop provides an easy morning walk or bike ride through meadows and over a picturesque covered bridge. The historic Main Street, with its colorful storefronts and chef-owned restaurants, gives you walkable access to everything from farm-to-table dining to locally crafted goods. Weekend afternoons might find you at The Vineyard at Windham, sampling New York State wines while taking in mountain views from their terrace. And with Elm Ridge Wild Forest's extensive trail network nearby, you'll never run out of new places to explore, whether you're an avid hiker or simply enjoy a peaceful walk in the woods.
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Listing information last updated on February 11th, 2026 at 5:05am EST.