Commercial: MLS #12527859

5255 W Madison Street offers investors a stabilized, cash-flowing retail asset with in-place income, a strong 9.5% cap rate, and documented actual operating numbers. This income-producing property is ideal for buyers seeking passive income, low CapEx exposure, and long-term hold stability. The property has been owned and meticulously maintained by the same ownership for several decades, reflecting true pride of ownership rather than deferred maintenance. Significant capital improvements have already been completed, including a brand-new roof installed within the last two years, electrical upgrades, and continued preventative maintenance throughout the building. The result is a turnkey investment with no known deferred maintenance and minimal near-term capital requirements. The asset generates approximately $129,900 in gross annual income with an in-place Net Operating Income of $76,252, based on actual expenses and zero vacancy loss. Operating costs are well controlled, tenants occupy individual retail spaces, and utilities are tenant-paid where applicable, further strengthening cash flow durability. Constructed of classic brick, the building is positioned along West Madison Street, a high-visibility, high-traffic urban retail corridor serving dense residential neighborhoods. This neighborhood retail location continues to support consistent demand from service-oriented and necessity-based tenants, making it a resilient asset across market cycles. With strong in-place income, recent capital improvements, and long-term ownership history, this property is well suited for 1031 exchange buyers, private investors, and groups seeking a stabilized Chicago retail investment at a favorable basis relative to replacement cost.