A rare offering in the heart of St. Helena. An expansive .52-acre in-town property combining single-level living, a five-bedroom compound layout, and exceptional proximity to downtown. Located on one of St. Helena's most historic and picturesque streets, just moments from the town's renowned dining, tasting rooms, and shops, this thoughtfully rebuilt residence offers a rare blend of scale, privacy, and flexibility within the city limits. Set across a generous and uncommon parcel, the property features a three-bedroom, two-and-a-half-bath main residence designed for entirely single-level living, complemented by a fully detached two-bedroom, two-bath ADU and oversized 2-car garage. Originally rebuilt from the ground up in 2006, the home presents a classic Craftsman exterior that opens to a warm, design-forward interior. Vaulted wood-beamed ceilings, abundant natural light, and curated finishes create a sense of quiet sophistication throughout. The home has been thoughtfully refreshed under the direction of renowned interior designer Jay Jeffers, resulting in a refined and cohesive aesthetic throughout. The spacious kitchen anchors the home and flows seamlessly into inviting living and dining areas, while the primary suite and guest bedrooms offer comfort and separation. The grounds unfold into a private backyard retreat, where manicured garden spaces, several thriving citrus trees and multiple outdoor gathering areas create a setting that feels both expansive and intimate. A generous pool and spa serve as the focal point, complemented by a pool house and thoughtfully designed spaces for entertaining and relaxation. Private and serene, yet exceptionally close to the best of St. Helena, this is a rare opportunity to own a fully realized Napa Valley compound offering scale, versatility, and enduring appeal.