Perched at the end of a peaceful South Wilton cul-de-sac, 43 Chessor Lane is a rare opportunity to own a custom-built masterpiece crafted by one of the area's most respected builders-for his own family. Designed with uncompromising quality and exceptional attention to detail, this home combines timeless elegance with cutting-edge technology for an elevated lifestyle. A new sweeping Belgian block-lined drive welcomes you to over 5,000 SF of refined living space, where thick crown moldings, coffered ceilings, and hand-finished millwork make a lasting impression. The sun-drenched chef's kitchen flows seamlessly into the family room, where a retractable projection screen and built-in surround sound create the ultimate home theater experience. A whole-house CAT 5 network, Control4 system, and six audio zones allow smart customization throughout. The primary suite features a spa-inspired bath, private sitting room, and balcony retreat. With five spacious bedrooms and 4.5 baths, every space is thoughtfully designed - with room for third floor expansion. A walk-out lower level with fireplace offers added living space and flexibility. Outside, professionally landscaped grounds offer room for pool, a bluestone patio, built-in fireplace, and intimate garden paths. Located within Wilton's award-winning school district and just minutes to shops, train, and town center-this home embodies both privacy and connection in one extraordinary setting.