Double the charm, double the opportunity with "The Two Madelines" in Oakland's fabulous Upper Dimond district! This rare, completely remodeled property features two distinct homes on one lot, each with its own address (3017 and 3019 Madeline Street), individual washers/dryers, and crisp air conditioning. The main house ("Big Maddy") is a gorgeous 1930s two-bedroom/one-bathroom bungalow boasting 2026 upgrades, a drought-resistant rock garden with classic California curb appeal, a welcoming front porch, and airy vaulted ceilings over an open-concept living, dining, and kitchen space. Tucked behind is "Lil' Maddy," a detached, two-story one-bedroom/one-bathroom ADU featuring a downstairs lounge, an upstairs mini living room, and a garage underneath for covered parking or massive storage. A long driveway accommodates multiple cars, while the sprawling, flat yard offers a secure, blank canvas ready for your dream outdoor oasis. Minutes from commuter freeways, the vibrant Fruitvale shopping district, and local staples like the original Loard's Ice Cream (Bay Area natives, IYKYK!), this versatile gem is a turnkey masterpiece perfect for multi-generational living, a savvy rental investment, or a live-in-one, lease-the-other dream!