Set high above the surrounding countryside, where eagles glide and the air shifts a little quieter, this extraordinary hilltop retreat offers architectural distinction, total privacy, and a true sense of escape - approximately two hours from the bustle of New York City. A winding, forested drive reveals the home gradually, heightening the arrival. Custom-built with Californian and Japanese influences, the residence is thoughtfully plotted to capture sweeping views and natural light through a dramatic curved wall of floor-to-ceiling windows. A soaring two-story stone chimney anchors the space, with steel beams fanning outward to frame the landscape like living art. Inside, the scale is grand yet warm. Radiant-heated bluestone floors, wood and stone sourced from the property, and refined natural finishes create a grounded, elevated feel. The open living and dining area flows into a true chef’s kitchen with marble countertops, Wolf range, Sub-Zero refrigeration, Gaggenau steam oven, walk-in pantry, and a pizza oven built into the bluestone fireplace. Just beyond, a screened-in porch invites slow mornings and long evenings wrapped in nature. The main level includes a serene primary suite, while upstairs offers two generous additional bedroom suites with stunning views, one with a traditional Hinoki soaking tub offering a truly unique self-care moment. A suspended balcony overlooks the living space, perfectly positioned to take in the ever-changing panoramic view of the mountains and the countryside below. Thoughtful details include towel warmers in each bathroom, a dedicated tea kettle burner and two sinks in the kitchen, and a dumbwaiter from the garage to the pantry. A full, unfinished lower level offers flexibility for an artist studio, gym, or workshop, along with two-car garage access. While the property itself is the epitome of privacy, Callicoon Center is central to so many great destination towns, with Callicoon, Livingston Manor, Roscoe, North Branch, and Jeffersonville only 10-20 mins away. A myriad of fine and fun dining can be found in the area starting right down the road at Conover Club at Callicoon Hills, and there are dozens of amazing local businesses to support! This area is famous for its sweeping rural beauty and fly fishing, in addition to tons of hiking, swimming, kayak/canoeing, and more. Two hours to the GWB in NYC.
Impressive New Construction. Located in the heart of the Catskill Mountains and minutes from Livingston Manor, Callicoon, and Roscoe, this 3-bedroom, 3-bath Cape Chalet offers 2,345 square feet of well-designed living space on 3 private acres. The home features an open-concept layout with a seamless flow from the kitchen to the main living area, an indoor balcony, an outdoor patio, and multiple outdoor spaces, ideal for entertaining or relaxing. Large trapezoid windows and glass-paneled doors provide abundant natural light and bring the outdoors in. Two bedrooms offer en-suite baths with quality tile finishes, creating flexible living options and added privacy. The second-floor primary suite includes a loft-style library and a private balcony overlooking the main living space. The basement is partially finished, adding 1300sq ft of living space. (STR) Potential: The layout, multiple en-suite bedrooms, and proximity to popular Catskills destinations make this property well-suited for short-term rental use. Conveniently located near dining, shops, hiking, fishing, and year-round recreation, this property offers flexibility for full-time living, a second home, or income-producing potential. Additional highlights include: 10 total rooms with flexible uses (home office, guest space, studio); propane heat for efficient year-round living; a fire pit area for outdoor enjoyment; a woodsy setting with privacy, universal EV charger, backup generator, and usable acreage.
Overbrook House is a design-forward Catskills retreat on nearly an acre that lives much larger thanks to multiple eye-popping indoor/outdoor spaces including a dreamy separate Guest Studio (not included in square footage). The meticulously styled main house features a den paneled with reclaimed barnwood, while the more formal living room's gas fireplace is great for ease of use and tidiness. A bright enclosed porch welcomes you inside, and the cheerful country kitchen with open shelving flows into a spacious dining room. French doors open to a covered outdoor patio with wood ceiling, perfect for dining and lounging. Three bedrooms (one on the main floor) and two full baths offer flexibility, and all rooms reflect a cohesive design aesthetic. The detached Guest Studio upstairs in the barn feels like a designer treehouse, with a full kitchen, bath, queen bed and lounge area surrounded by windows. Furnishings and contents of the studio are included (contact for more info). The heated pool with cedar deck and auto-cover is a showstopper, complemented by a restored 1957 Airstream, custom fire pit, and multiple areas for al fresco dining. Tucked behind the barn is “the grotto” — a hidden nook with a spot to dine or unwind. Cross a private footbridge over Buck Brook to reach Callicoon Hills for a meal or live music at the summertime band stand. Offered furnished (with exclusions); adjacent buildable half-acre lot also available.

Callicoon Center is located in New York. Callicoon Center, New York 12724has a population of 404. Callicoon Center 12724 is less family-centric than the surrounding county with 0% of the households containing married families with children. The county average for households married with children is 27.82%.
The median household income for the surrounding county is $63,393 compared to the national median of $69,021. The median age of people living in Callicoon Center 12724 is 64.3 years.
The average high temperature in July is 79.8 degrees, with an average low temperature in January of 12.6 degrees. The average rainfall is approximately 48.2 inches per year, with 61 inches of snow per year.