A rare hillside retreat in Portland's SW Hills, this 4-bedroom, 3-bath 1909 Craftsman blends timeless character with thoughtful modern updates in a private, vineyard-like setting. Tucked away yet just minutes from downtown, the home offers a unique balance of convenience and escape-complete with four on-site parking spaces. Inside, hardwood floors, abundant natural light, and a gas fireplace create warm, inviting living spaces. The kitchen combines function and charm with built-in elements, while skylights on the upper level enhance the home's bright, expansive feel. Designed for comfortable living and relaxed hosting, the layout welcomes guests with ease. The flexible lower level offers strong ADU potential with space for guests, creative work, or extended living, and additionally includes a wine or root cellar along with a separate studio and storage areas. Major system updates and interior and exterior improvements have been completed, offering a move-in ready home with lasting peace of mind. Outdoors, the surrounding greenery and established landscape with fruit trees create a setting that feels tucked away without sacrificing access to the city. A cedar sauna and hot tub add a spa-like element to enjoy at home. Set alongside Governors Park and near the Marquam Trail, the location provides immediate access to green space and nearby hiking while remaining close to Portland's urban core.