404 Winter Clove Road, Round Top

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.