3 Bold Westport Estates and a Hidden Hills Contemporary Retreat

Rising along one of Westport’s most coveted addresses, this estate pairs bold, sculptural architecture with interiors described as meticulously composed—spaces that feel discovered rather than designed. Walls of glass draw daylight deep inside and blur the boundary between indoors and out, while expansive balconies extend everyday living into the open air. Outside, a resort-caliber pool anchors the experience, complemented by a fully equipped outdoor kitchen for long, unhurried afternoons and easy evenings with friends. Lush, manicured grounds frame each moment, offering a sense of privacy and calm without needing to leave the property. The listing notes that photos are renderings and represent the builder’s work, setting an expectation of a carefully executed vision. Life here is defined by light, air, and seamless transitions from inside to out.

Set on over two private acres in the heart of Westport, this residence balances refined design with a setting that feels quietly removed—yet remains minutes from downtown, Compo Beach, and the train, with New York City about an hour away. Interiors are thoughtfully scaled for both everyday ease and entertaining, anchored by a double-island chef’s kitchen. The primary suite reads as a true retreat, with a private balcony for morning air or an evening pause. A finished third floor and an expansive lower level extend the home’s flexibility, offering additional places to work, gather, or unwind. Outdoors, the lifestyle shifts seamlessly: a heated Gunite pool, an all-season hot tub, and a covered porch with a fireplace create year-round destinations. With room for tennis, the grounds invite long afternoons at home and unhurried weekends that feel like a getaway.

Beyond the guard gates of Hidden Hills, this re-imagined single-story contemporary is ideally set on 4.5 acres, offering privacy alongside unobstructed city light and mountain views. Recently rebuilt using the finest finishes, the home unfolds across an open-concept floor plan that connects living, dining, and family rooms with ease. At the center, an island kitchen anchors daily life and entertaining, while 25-foot Fleetwood pocket doors extend the living spaces outward for true indoor/outdoor flow. Five bedrooms and 4.5 bathrooms support both quiet retreat and hosting. Outside, resort-quality grounds feature a pool and spa, a covered outdoor living room, and manicured lawns. A lower-level equestrian center—with barn, tack and feed rooms, and a corral—rounds out a setting designed for expansive, unhurried California days.