Positioned in the heart of Chicago's historic Woodlawn neighborhood, this classic two flat presents an attractive opportunity for investors, owner occupants, and buyers seeking long-term value in an evolving South Side market. The property combines the enduring appeal of a traditional Chicago multifamily with multiple avenues to enhance income, improve value, and build equity. The building features two residential units: a 2 bed /1 bath first floor unit and a 3 bed /1 bath second floor unit. Both apartments offer generous living areas, abundant natural light, high ceilings, and the architectural character associated with Chicago's classic two flats. A full basement provides valuable storage and potential for future expansion or additional usable space, while on site parking adds convenience and enhances tenant appeal. From an investment perspective, the property offers several compelling strategies, including buy and hold, value add renovation, rental income optimization, and owner occupant house hacking. Investors have the opportunity to capitalize on the property's existing two units while exploring improvements that could increase rents, strengthen tenant demand, and enhance long term asset value. The property is situated near the University of Chicago, Jackson Park, and the Obama Presidential Center, as well as the ongoing redevelopment and investment throughout the Woodlawn corridor. Continued neighborhood revitalization, proximity to major institutions, transportation, parks, and cultural amenities provide a strong foundation for future demand and potential appreciation. For investors looking to acquire a multifamily asset in a neighborhood undergoing significant transformation, this Woodlawn two flat offers a compelling combination of income potential, value add upside, and long term appreciation prospects. Tenant on 1st floor pays $1650/month for rent plus utilities.

Listing Courtesy of MRED as distributed by MLS Grid of EXIT Strategy Realty



Based on information submitted to the MLS GRID as of 2026-09-10 02:31 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: 2026-09-10 02:31 PM UTC
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