Nestled at the end of a quiet dead-end street in the true heart of Midtown, this charming .21-acre property offers a rare blend of historic character and modern flexibility. The main home showcases the timeless appeal of a classic Bend bungalow with tasteful updates throughout, while the nearly new ADU, completed in 2024, adds fresh, functional living space with views of Broken Top. Thoughtfully designed for privacy, both homes enjoy separation thanks to mature landscaping and generous spacing on the lot. Take in views of Mt. Bachelor from the welcoming front porch or enjoy the convenience of being just blocks from local favorites like the Yacht Club and within walking distance to downtown. Ample parking includes a 1.5 car detached garage for the main home and a spacious 1.5-car attached garage for the ADU. With both residences successfully rented over the past 18 months, this is a unique opportunity for investment, multigenerational living, or a live-in-one, rent-the-other lifestyle.