A rare opportunity on one of Healdsburg’s most iconic and sought-after streets – this showplace compound is in a historic district just blocks from the Plaza. The 4BD/5BA main home has been extensively remodeled with timeless charm and modern luxury, including a showstopping chef’s kitchen with premium Hestan appliances and White Macaubas leather quartzite slab counters, great room with disappearing multi-slide stacking and pocketing glass doors to the outdoors, and a spacious wine cellar for 800+ bottles with separate tasting lounge and adjacent half bath. The main-level primary suite features pool access and a spa-like bath; a second primary upstairs plus two more bedrooms and another full bath, complete the main home. The 2BD/2BA ADU has its own address and feels like a second home with full kitchen with Ijen Blue quartzite counters, laundry, and pool access from every room. Resort-style outdoor living includes a pool and spa, covered outdoor kitchen with Mugnaini pizza oven, Hestan appliances, Pietra Cardosa honed limestone counters, refrigerator drawers, ice machine, and multiple areas to entertain. The detached, fully restored garage offers a gym, temperature control, EV charger, and gated driveway. An extraordinary in-town retreat.