7741 S Yates Boulevard Welcome to this exceptional South Shore three-flat offering timeless Chicago architecture, generous living space, and outstanding investment potential. This classic brick building features three spacious units, each thoughtfully designed with large room sizes, abundant natural light, hardwood flooring, separate dining rooms, and versatile den spaces that can easily serve as home offices, sitting rooms, or additional bedrooms. Rich in vintage character, select units showcase beautiful built-in bookcases and original architectural details that blend seamlessly with tasteful updates. The property is currently producing income with two units occupied, while the vacant third-floor unit presents an outstanding opportunity for an owner-occupant or savvy house hacker to move right in while offsetting their mortgage with rental income from the other two units. For investors, the unit is also being actively marketed for lease, offering the flexibility to bring the building to full occupancy and maximize cash flow. The partially finished basement offers additional usable space and is ready for your finishing touches, creating even more potential to add value. A common-area coin-operated laundry provides an additional income stream, while the detached brick 3-car garage offers valuable parking and the opportunity for supplemental rental income. Completing the property are a rear porch and ample storage, enhancing both functionality and tenant appeal. Ideally situated in the heart of South Shore, you'll enjoy convenient access to Lake Michigan, Rainbow Beach, Jackson Park, the South Shore Cultural Center, the future Obama Presidential Center, Metra and CTA transportation, shopping, dining, parks, and major expressways. Whether you're looking to expand your investment portfolio or take advantage of a rare owner-occupied house hacking opportunity, this is your chance to own a well-maintained, income-producing building in one of Chicago's most historic and steadily revitalizing lakefront neighborhoods. Schedule your private showing today!