You see the stair tower before almost anything else—curved, cedar-sided, and rising beside the front door. It’s the first clue that this house was designed by someone thinking beyond straight lines and predictable rooms. The setting is just as distinctive. More than four acres unfold along famed Filippini Pond, a spring-fed spot loved for kayaking, boating, and fishing, with its own place in local lore as the popular skinny dipping destination for attendees of the original Woodstock festival of 1969. Bethel Woods Center for the Arts is steps up the road, making the area’s creative history feel less like the past and more like part of the neighborhood. The house has some architectural bona fides of its own, having received architectural awards - and inside, the reasons reveal themselves gradually. A sweeping staircase wrapped in warm wood forms the center of the home. Curved walls lead into unexpected spaces, custom built-ins appear from room to room, and nearly every turn offers a new perspective on the house or the water beyond it. The kitchen and dining area sit just beyond the entry, but the living room is where the home really announces itself. A modern wood-burning fireplace anchors the space, which opens into a soaring solarium with terracotta floors, woven ceiling panels, and walls of glass facing the pond. Sunlight moves across the room throughout the day, and the tranquil pond seems to find its way into every view. Then things get a little more fun. The former billiard room and is open to reinvention, while the adjoining party room comes fully prepared: hot tub, indoor grill, wet bar, wood-burning stove, & wine fridge. It’s unapologetically over the top in the best way: a room made for long weekends, late nights, and friends who end up staying longer than planned. Nearby, a substantial room with its own private entrance has been used as a home office. With its scale and separation from the main living areas, it could just as easily become a studio, guest space, or something entirely personal to its next owner. Upstairs, a generous landing offers another flexible place to work, read, or retreat. The primary suite begins with a sitting room overlooking the living space below, followed by a bedroom with a built-ins facing the water. It feels a little like the captain’s quarters on a very handsome ship. The primary bath carries the home’s gloriously retro swank, with warm wood, a series of private chambers, and its own sauna. Two additional bedrooms and a second full bath complete the level, with one more flexible space waiting above on the third floor. Outside, the expansive, flat, fully fenced yard offers plenty of room to gather, garden, play, or simply spread out. A broad stone patio looks over the pond, and two private docks make it easy to launch a kayak, cast a line, or sit at the water’s edge doing absolutely nothing. There’s a detached two-car garage for practical purposes, plus a second one-car garage that needs some love but has the makings of a studio, workshop, or something much more interesting than a place to park. There are easier houses to sum up. This one rewards curiosity. It’s bold, playful, wonderfully unconventional, and full of the kind of character that can’t simply be added later. What’s here is irreplaceable; what happens next is up to you.

Eat-in Kitchen, Garage, Walk-In Closet(s), Waterfront