Exceptional Investment Opportunity! Welcome to 5419 S Hermitage Avenue - a solid, income-generating two-flat with tremendous upside potential. Built in 1918 and brimming with classic Chicago character, this approximately 3,000 sq. ft. multi-family property sits on a 3,750 sq. ft. lot and delivers both immediate cash flow and long-term value. The main structure features two well-appointed residential units, each offering 3 bedrooms and 1 bathroom. A third unfinished unit presents a rare value-add opportunity: bring your vision and unlock additional rental revenue or create a private owner's suite below grade. Area residents enjoy a commuter-friendly lifestyle with the Orange Line just 5 minutes away and easy access to Ashland and Halsted corridors for north-south travel throughout the city. The flat terrain and dedicated bike lanes make cycling a breeze, while multiple shopping centers, parks - including Gage Park, Ogden Park, and McKinley Park - and restaurants are all within easy reach. Lake Michigan is just 5 miles away, and Chicago Midway International Airport is a quick 4.7-mile drive. Rear parking with private driveway Proven rental market in a neighborhood on the rise Minutes to public transit, major expressways, and the University of Chicago Whether you're a first-time investor, a seasoned landlord, or a savvy house-hacker, 5419 S Hermitage Ave offers the flexibility, space, and upside to make it work for you.

Listing Courtesy of MRED as distributed by MLS Grid of Real Estate Growth Partners



Based on information submitted to the MLS GRID as of 2026-03-09 10:56 PM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Last checked: 2026-03-09 10:56 PM UTC
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