Set in a coveted estate enclave prized by CEOs and captains of industry, this exceptional, shingle-style residence embodies timeless architecture, extraordinary craftsmanship, and meticulous attention to detail. Built custom for a CEO, the home showcases uncompromising quality and gracious curb appeal that leave a lasting impression. Designed for seamless indoor-outdoor living and grand-scale entertaining, sun-filled interiors with soaring 10-foot ceilings open to a resort-style pool, stone patios, stone fire pit and covered porch with fireplace for effortless year-round gatherings. Extensive bespoke millwork, six fireplaces, and refined architectural finishes elevate every space. The spacious level and private property is framed by mature landscaping, with school bus service directly at the driveway and an option to walk-to-school too as they are just 2/10 of a mile away. At the heart of the home, an extraordinary chef's kitchen with Thermador and Wolf appliances, dual islands, two dishwashers, walk-in pantry, and fully equipped entertainer's pantry with wet bar anchor daily life and entertaining. The primary suite is a private sanctuary with turreted sitting room, fireplace, and dual walk-in closets. Six ensuite bedrooms plus separate guest suite over the garage offer exceptional accommodations. New cedar roof, new boiler, new wine cellar, and significant upgrades complete this rare offering of stature and sophistication in one of Westport's most prestigious settings.