Rarely does one property capture everything that makes Rowayton so special-architectural character, resort-style amenities, exceptional privacy, expansive outdoor living, and an effortless walk to the village, beach, train, and waterfront. Welcome to 60 Crooked Trail! Nestled on over an acre at the end of one of Rowayton's most desirable cul-de-sacs, this exceptional home offers the perfect blend of timeless architecture, modern luxury, and effortless coastal living. Dramatic cathedral ceilings, exposed wood beams, abundant natural light, rich millwork, and a stunning floor-to-ceiling stone fireplace define the main living spaces, while the chef's kitchen features premium appliances, custom cabinetry, generous workspace, and a wood-fired pizza oven. Designed for exceptional indoor-outdoor living, multiple French doors open to a wraparound covered porch, expansive stone terraces, outdoor kitchen with built-in grill and fireplace, sparkling gunite pool, renovated pool house, outdoor shower, bocce court, and beautifully landscaped level lawns-creating a private resort ideal for entertaining or everyday enjoyment. The first-floor primary suite is a private retreat with cathedral ceilings, exposed beams, a stone fireplace, sitting area, two custom walk-in closets, dressing area, and a spa bath with heated floors and steam shower.