Nestled on a leafy, tree-lined corner in the heart of Ladd's Addition—one of Portland's most cherished & architecturally significant neighborhoods—this storybook Tudor offers a rare blend of timeless character, thoughtful updates, and modern sustainability. Located across from the iconic Ladd Circle Park & Rose Gardens, the home sits in Portland's oldest planned residential community, known for its diagonal street grid, lush tree canopy, historic homes, and rose-filled traffic circles. Enjoy living blocks from the vibrant Division & Hawthorne shopping districts, New Seasons Market, and award-winning restaurants. The main level is ideal for entertaining, with the living room—anchored by a Pratt & Larson tile-surround wood-burning fireplace featuring a high-efficiency insert that provides supplemental heat—flowing seamlessly through historic arches into the dining area & a updated kitchen featuring a Bosch range, farmhouse sink, quartz countertops, and tile backsplash. Upstairs, the primary includes a walk-in closet & room to add a potential 2nd bathroom, while the lower level offers flexibility. Currently used as a guest space, home gym, and extra storage, it also holds potential for further build-out. Two patios offer private outdoor retreats, including an expansive, fully fenced stone patio perfect for al fresco dining. The low-maintenance garden—recognized by the Backyard Habitat Certification Program—has been granted Platinum certification & was planted with Pacific NW natives that support local pollinators. Over $100k in recent improvements elevate the home's aesthetics, comfort, and efficiency, including 2021 exterior paint, Schoolhouse lighting, a high-eff heat pump, EV charger, 200-amp panel, upgraded appliances, and extended driveway. One of the few historic homes in Portland to earn an exceptional 9 out of 10 Home Energy Score. This extensively updated Ladd's home is more than a place to live—it's a piece of Portland's history, renovated for modern living. [Home Energy Score = 9. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10238875]