Set on a pristine, level acre on one of Westport's most popular cul-de-sacs, this exquisite stone & shingle home combines timeless craftsmanship with modern luxury. Featuring 9' & 10' ceilings, extensive millwork, and five fireplaces with custom mantles, the home is built for elegant living and entertaining throughout nearly 9000sqft. The main level offers a chef's kitchen that flows into a warm family room with a stone fireplace and French doors to the patio, a cherry-paneled study, formal living room with marble fireplace, and a dining room that easily seats 20. Upstairs are five spacious bedrooms and four full baths, including a luxurious primary suite with 12ft ceilings, a fireplace and an oversized double shower with steam. A large playroom offers a potential in-law/au pair suite with its own bedroom and full bathroom. The finished walkout lower level includes a media room with large screen, gym, games room, a second family room with a fireplace, and full bath. The walk-up attic offers approx. 1500 sq ft for future expansion. Outside, enjoy a private backyard oasis with a heated 20x50 Gunite pool and spa (2018), new stone walls and planting beds, patio with wood-burning fireplace, and professionally landscaped evergreens and ornamentals for privacy. High Point Road is a mile-long cul-de-sac that feels like its own neighborhood, uniquely within walking distance to all three schools: award-winning Staples HS, Bedford Middle, and Long Lots Elem. Book your showing today!