50 Holly Rd

Welcome to Twin Bear Chalet, a cozy A-frame retreat tucked along a babbling creek in Napanoch, NY, just under two hours from New York City. Set on a half acre surrounded by native wildflowers, berries, and fruit trees, this 2 bedroom, 1 bath chalet offers the perfect blend of privacy, serenity, and rustic charm.

Step inside and you'll find rough-cut pine paneling throughout, crafted by the original owner—a builder and artist whose handmade ironwork staircase tells a whimsical Catskills story of deer, squirrels, and bears. The open living space glows with natural light, while the upstairs loft provides a spacious second bedroom that opens to a three-season sleeping porch overlooking the forest and Trout Creek. Fall asleep to the sounds of the creek and wake to birdsong and mountain air.

Recent updates include a new kitchen sink and lighting, upgraded plumbing, septic service (2023), and a new Generac whole-home standby generator (2023) so you can enjoy peace of mind and modern comfort in a timeless setting.

Outside, garden boxes and native plantings invite you to harvest blueberries, blackberries, raspberries, grapes, cherries, paw paws and apples right from your yard. The unfinished basement offers room to expand, add a bedroom, studio, or workshop to suit your vision.

Backing up to over 10,000 acres of state land just minutes from the Rondout Reservoir, and a short drive to Peekamoose Blue Hole, Minnewaska State Park, and Mohonk Preserve, this home is ideally located for year-round adventure. Whether you're seeking a weekend escape, a creative hideaway, or a vacation home; Twin Bear Chalet is a rare Catskills gem, a place to reconnect with nature and slow down life's pace.