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Turnkey Entertainment-Zoned Event Estate with Two Homes in the Heart of the Catskills. Discover the iconic Round Top Arts & Retreat House—a 6.3-acre estate with extraordinary business, hospitality, wellness, and entertainment potential in one of the Catskills' most storied resort enclaves. Less than 2 hours from NYC and 30 minutes to Hunter & Windham, this property sits at the crossroads of heritage, natural beauty, and modern retreat culture. Where History, Landscape & Creativity Meet: Round Top has long been a hidden haven for city dwellers seeking cool mountain air, forested ravines, and easy access to the region's famed water features. Set in a valley carved by Kiskatom Brook (known near the resorts as Winter Clove Brook), the area blossomed into a beloved weekend-getaway landscape—home to waterfalls, natural swimming holes, and breezy summer retreats. Today, this region is thriving again in a new Catskills renaissance, drawing wellness travelers, artists, and boutique-minded guests who seek nature immersion with creative flair. At this property's edge, just steps from the grounds, begins the Round Top Trail Network—locals call it ''Roundtopia''—a public system of scenic singletrack and doubletrack paths connecting legacy resorts such as Winter Clove Inn, Glen Falls House, and Riedlbauer's. The trails wind through forest ridges, bridge-crossings, and creek-carved ravines leading to beloved landmarks like Artist Falls, the historic Alfred Clark Bridge, Winter Clove's cascades, and Venus' Bath, a natural stone ''tub'' in the brook. For nature lovers, yogis, cyclists, and wellness-retreat leaders, this setting is a profound invitation to slow down, unplug, and recenter your chi. The Estate- A true multi-venue compound with exceptional mountain views, ideal for: • Destination weddings & outdoor events • Retreat centers & wellness programs • Boutique country inn or AIRBNB investment • Music, dance & recording artists • Cultural center, or creative studio • Hospitality entrepreneurs & off-premise caterers Main Chalet (6,748 sq ft | 6 BR | 7 BA)- A striking post-modern chalet anchors the property, offering expansive entertaining areas, multiple bedroom suites, and serene gathering spaces. The home includes: • A 2,500 sq ft commercially zoned ballroom—crafted with sound-optimizing materials and historically used by renowned opera singers who rehearsed here before appearing on Broadway. • Sauna, hot tub, deck, patio, and 2-car garage • Large flat lawns with panoramic Kiscatom Mountain vistas—ideal for tents, ceremonies, concerts, and open-air wellness programming. Second Residence — Cape House (3 BR | 2 BA): A versatile guest, staff, or rental home with a kitchen/living combo, offering additional lodging or operational flexibility. Already zoned Recreation/Entertainment, significant acreage, and strong event-driven demand in the region, this property offers exceptional scalability for investors. Expansion is possible pending permits—ideal for cabin suites, studio buildings, or wellness-oriented structures. An Unmatched Opportunity: For hospitality professionals, investors, musicians, yoga instructors, nature enthusiasts, and creators seeking an extraordinary location in the Great Northern Catskills, this is a chance to own a legacy property in a rediscovered mountain community where waterfalls, forests, art, and renewal meet. The Round Top Arts & Retreat House—a place where the past echoes in song, the mountains inspire new visions, and every pathway leads back to nature. 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 2:35am EST.