Set along one of Healdsburg's most picturesque streets, this rare find features two separate bungalow-style homes on a spacious 1/4 acre parcel just minutes from Healdsburg Plaza. With turn-of-the-century character and a just-remodeled interior, the primary home (#133) is a perfect blend of historic and new. Classic bungalow-styling features two bedrooms and one bathroom, approximately 750 sq.ft. of living space, all updated to please the modern aesthetic. Tall ceilings and windows, LED lighting, an inviting front porch, new cabinetry and appliances, luxury vinyl plank flooring, and an energy-efficient mini-split system make this home ready for you to move right in and enjoy. The second home is set to the back of the parcel with its own private entrance and separate house address. Built in a cottage style, this sweet unit is one bedroom, one bath with approximately 647 square feet of living space. The interior is freshly painted with new lighting fixtures. Both homes have air-conditioning, laundry, separate detached garages, and fully fenced yards. This property is truly unique. Two homes on a 1/4 acre lot, two separate addresses, two electric meters, and two water meters. Whether you're envisioning a private family compound, a wine country getaway with guest accommodations, multi-generational living, or the flexibility of a primary residence paired with a second home, the possibilities are as timeless as the homes themselves. Just 0.7 mile from celebrated Healdsburg Plaza, enjoy the perfect balance of neighborhood charm and world-class dining, wineries, and boutique shopping.