Multi Family homes for sale & real estate in South Side, IL

Multi Family Home for sale in South Side, IL:

Looking for what might be the best 2-flat in all of Chicago? This is the one you've been waiting for! Welcome to 6111 S Eberhart, a stately and beautifully maintained legal 2-flat located in the heart of red-hot Woodlawn, one of Chicago's fastest-growing and most iconic neighborhoods. This is a rare opportunity for either the savvy house hacker looking to live in one unit and rent the other, or the forward-thinking investor seeking tax-advantaged cash flow, rising rents, and long-term appreciation. Each unit is rich with character and thoughtfully updated, blending timeless 1910 architectural details with modern-day comforts. The first-floor unit features 3 spacious bedrooms, 1 sleek bathro

Multi Family Home for sale in South Side, IL:

Exceptional investment opportunity in a prime Hyde Park location. Solid all-brick 2-unit building with a potential bonus garden apartment presents the perfect opportunity for investors or owner-occupants looking to build sweat equity. The main floor features a spacious 3-bedroom, 1-bath unit, while the upper level offers a generous 4-bedroom, 1-bath layout. The finished walk-out basement was configured as a 2-bedroom, 1-bath unit with laundry hookups-ideal for added rental income. Situated on an extra-deep, fully fenced lot with a 2-car garage, this property is just blocks from the University of Chicago campus and the future Chicago Medicine cancer center, ensuring a steady stream of studen

Multi Family Home for sale in South Side, IL:

Beautifully rehabbed in 2025, this solid two-unit building in the heart of Bridgeport offers the perfect blend of modern design and timeless Chicago charm. The first-floor unit features 3 bedrooms and 2 bathrooms, while the second-floor unit offers 4 bedrooms and 2 bathrooms-each with an open layout, abundant natural light, and its own laundry room for added convenience. Everything is brand new, including siding, plumbing, electrical, kitchens, bathrooms, and appliances. Both units showcase modern finishes, sleek cabinetry, quartz countertops, contemporary lighting, and updated flooring throughout. The property also includes a 2-car garage and a low-maintenance backyard, ideal for city livi

Multi Family Home for sale in South Side, IL:

RARE WOODLAWN 3-FLAT Greystone with EXCEPTIONAL unit sizes & PREMIUM cash flow. Meticulously maintained by current owner with extensive recent upgrades including COMPLETELY RENOVATED laundry area & full plumbing overhaul. THE STANDOUT: Massive duplex unit (1st floor) - SIGNIFICANTLY LARGER than typical Woodlawn 3-flat conversions. Currently commanding TOP-OF-MARKET rent - PROVEN income, not projections. CURRENT PERFORMANCE: Strong existing cash flow with TWO occupied units. FULLY OCCUPIED PRO FORMA: Substantial income potential with significant upside. LOCATION ADVANTAGES: Walking distance to UChicago Main Campus, UChicago Law School, UChicago Medical Center, Obama President