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Discover a rare Catskills retreat in Round Top, NY, offering 6.3 peaceful acres with open land, wooded edges, and sweeping mountain views. Ideal as a weekend escape or full-time residence, this property includes two beautiful homes, modern amenities, and nearby access to trails, waterfalls, and local dining. It blends total privacy with a prime location close to Hudson, Woodstock, ski resorts, and year-round recreation. The main home is a striking 6,748 sq ft postmodern chalet (including the finished basement) filled with natural light and designed for comfort, creativity, and entertaining. Its dramatic centerpiece is a 2,500 sq ft great room with soaring ceilings and exceptional acoustics—a space once used by opera performers and perfect for gatherings, celebrations, music, or quiet relaxation. With six bedrooms, seven bathrooms, central A/C, and an attached two-car garage, the home delivers spacious living with modern convenience. Zoning for residential and entertainment use offers added flexibility for hosting events or retreats. The residence is equipped with a whole-house generator, security system, and direct-to-station fire alarm, providing peace of mind. The finished basement adds more than 2,000 sq ft of flexible living space, including a sauna, bathrooms, a laundry room, a large flex room suitable for a gym, studio, or recreation area, plus generous storage and a separate entrance that expands layout options even further. Outdoor living is a defining feature. An deck and patio with hot tub beside them, showcases beautiful mountain views, creating a resort-like experience year-round. Below, a stone patio and fire pit offer additional space for relaxing and entertaining. Thoughtful landscaping enhances curb appeal while maintaining a low-maintenance, natural look. A second home, a charming Cape-style guest house, adds significant versatility. With three bedrooms, two bathrooms, and an open kitchen-living layout, it's ideal for multi-generational living, rental potential, private guest accommodations, or a dedicated creative retreat. The dual-home setup makes the property especially attractive for buyers seeking space, privacy, and flexibility. The location elevates the entire lifestyle. A bike trail directly behind the property leads to waterfalls, swimming holes, and wooded stretches perfect for hiking and biking. Round Top restaurants are close enough to walk to, offering convenience with small-town charm. Golfers will appreciate being only minutes from Blackhead Mountain's scenic course, while skiers can reach Hunter and Windham Resorts in about thirty minutes. Nearby towns like Hudson, Ashland, and Woodstock add arts, dining, and culture to your orbit, making this a true four-season destination. Whether you're seeking a private mountain retreat, a luxurious weekend getaway, or a spacious home with room for guests and gatherings, this property stands out as a rare Catskills offering. With two homes, stunning mountain views, extensive indoor-outdoor living spaces, and a prime location near top attractions, this estate delivers a lifestyle of relaxation, beauty, and possibility. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
The Upstate Lifestyle at 404 Winter Clove Road, Round Top NY
The location puts you within easy reach of some of the Catskills' most rewarding outdoor and cultural experiences. Kaaterskill Falls, one of New York's highest waterfalls at 260 feet, is just a short drive away, offering hiking trails that range from an easy viewing platform walk to more challenging terrain for those seeking adventure. Hunter Mountain and Windham Mountain, both under 20 minutes away, provide year-round recreation—downhill skiing and snowboarding in winter, and scenic gondola rides plus mountain biking in summer. For cycling enthusiasts, the Roundtopia trail network offers over 20 miles of mountain biking trails that wind through the area, with access points at several local resorts and scenic routes that pass waterfalls and lead to trailside beer gardens. The nearby towns of Tannersville and Round Top have developed a vibrant dining scene, with options ranging from farm-to-table restaurants like Jessie's Harvest House to German-themed spots reflecting the area's heritage. Winter Clove Inn, virtually next door, features a historic bowling alley, golf course, and extensive hiking trails on 300 acres, making it a wonderful neighbor for exploring additional recreation without having to drive far.
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Listing information last updated on January 17th, 2026 at 12:50am EST.