Perched high on Overlook Mountain just a mile from the heart of Woodstock, this striking contemporary residence—designed and built in 1995 by the iconic Bananas of Woodstock—is a rare architectural gem that seamlessly blends creativity, quality, and comfort. Privately sited among the trees, the home's unique design is constructed with steel beams throughout, cleverly concealed beneath rich wood caps. Walls of south-facing Pella windows flood the space with natural light year-round, offering passive solar warmth in winter and breathtaking views—extending all the way to the Ashokan Reservoir and even Mohonk in the distance. Warm cherry and oak floors run throughout, adding an organic elegance to the home's modern design. The current owners have lovingly enhanced the property over 25+ years with thoughtfully designed additions. A spacious two-car heated garage with a workshop and large storage closet was added, along with a fully equipped art studio featuring plumbing, A/C, and its own private deck and a full basement. In 2012, the home was expanded to include a stunning modern chef's kitchen with concrete and marble countertops and custom cabinetry, a large open dining room with built-ins, and a screened-in porch with an outdoor TV. Just beyond, you'll find a beautifully crafted stone barbecue area for al fresco entertaining. The primary suite features a spa-like bath renovated with a soaking tub, separate steam shower, and Toto Washlet. A second upstairs bedroom—currently used as a library—along with a half bath, was thoughtfully created from existing open space. Connected by an enclosed breezeway that doubles as a dramatic entry foyer, the guest wing offers its own private entrance and includes a living room, bedroom, and full bath—ideal for guests or a private work-from-home retreat. Or convert this to the primary suite for easy ground floor living. In addition, the guest wing has its own basement used for wine storage. A gorgeous 42-foot heated saline gunite pool, surrounded by expansive Brazilian hardwood decking, is complemented by a chic pool cabana, creating the perfect setting for summer gatherings and relaxation. Custom designed metal railings extend from interior curved stairway to the exterior patio and path leading to the pool below. Lush grasses and plantings enhance this mountain oasis. This iconic property is a one-of-a-kind offering that captures the spirit of Woodstock with modern luxury and architectural distinction. Nothing compares to this.