Exceptional investment and multi-generational living opportunity in the heart of Winnetka. This fully reimagined property features three separate units with three addresses, offering a total of 8 bedrooms, 6 bathrooms, and approximately 3,395 sq ft of living space across the main residence, an SB9 unit, and an ADU. The main residence (19918 Kittridge St) offers 3 bedrooms and 2 bathrooms across approximately 1,506 sq ft and has been extensively remodeled with an open concept layout, wide plank flooring, and abundant natural light. The modern chef's kitchen features two tone cabinetry and contemporary fixtures, while the bathrooms showcase dramatic marble tile and spa inspired finishes. The newly built unit (19920 Kittridge St) provides 3 bedrooms and 2 bathrooms in approximately 1,000 sq ft with a bright open floor plan, stylish kitchen, and modern finishes. Private balconies extend the living space outdoors and offer open views, creating a great place to relax and enjoy the surroundings. Completing the property is an ADU (19920 1/2 Kittridge St) offering 2 bedrooms and 2 bathrooms across approximately 889 sq ft with its own private entrance, full kitchen, and thoughtfully designed living spaces, ideal for rental income, extended family, or guests. Extensively renovated with contemporary design, quality materials, and low maintenance landscaping, the property also includes fully paid off solar panels, providing long term energy savings and added efficiency. This unique property offers flexibility for owner users, investors, or multi generational households seeking multiple income streams in a desirable Valley location close to shopping, dining, and major transportation routes. Whether you are looking to live in one and rent the others or maximize income potential, this is a rare opportunity to own a versatile and beautifully updated property. Schedule your showing today and explore all the possibilities.