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.

Property Details

PRICE
$264,000
BEDROOMS
6
BATHROOMS
2
SQFT
N/A
YEAR BUILT
1918
PARKING SPOTS
N/A
MLS #
12581608
FULL ADDRESS
5419 5419 HERMITAGE Avenue
CITY
Chicago, IL
ZIP
60609

Listing Details

Listing Office
Real Estate Growth Partners
Listing Agent
Lori Wyatt
Contact
312-545-1030
Last Data Update
2026-04-26T11:33:21Z

Interior

BATHROOMS
2 Full Bathrooms

Schools

School District
299
Elementary School
High School

Buy This Home With a Local Expert

22 years. 600+ Chicago closings. Individual, hands-on representation from first tour through close. Ken can be your buyer's agent on this property. Call 773.398.5585 or drop your details below.

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