Set in one of Westport's most prestigious estate enclaves, this exceptional shingle-style residence defines luxury living with a rare emphasis on multi-generational comfort, timeless architecture, and impeccable craftsmanship. Designed and built by a renowned architect and builder for a Fortune 500 CEO, the home reflects uncompromising quality, enduring design, and gracious curb appeal that impresses. Seamless indoor-outdoor living defines the home, with sun-filled interiors, soaring 10-foot ceilings, and an expansive walkout lower level with fireplace, all opening to a resort-style pool, stone patios, fire pit, and covered porch with fireplace, providing an effortless setting for entertaining. Extensive bespoke millwork, six fireplaces, and refined architectural finishes enrich every space. The expansive, level, and private grounds, framed by mature landscaping and abutting the 39-acre Newman Preserve, offer serenity with rare walkability to top-rated schools and 8 minutes to Westport's lively downtown. A spectacular chef's kitchen features Thermador and Wolf appliances, dual islands, 2 dishwashers, walk-in pantry, and a fully equipped butler's pantry with wet bar. The primary suite offers a turreted sitting room, fireplace, and 2 walk-in closets. Six ensuite bedrooms and a private suite over the garage provide flexibility for guests. New cedar roof, new boiler, new wine cellar, and extensive upgrades complete this rare offering in a premier Westport location.