565 W Randolph Street 565 W. Randolph St offers investors a unique opportunity to acquire a prime asset in Chicago's West Loop, a neighborhood celebrated for its dynamic blend of commercial and residential growth. This 59, 981 SF Class C office building, constructed in 1872, combines historical charm with modern functionality, featuring both a passenger elevator and a freight elevator. At $250 per SF with a purchase price of $14, 995, 000, this asset provides immediate stable cash flow along with significant value-add potential through a strategic conversion plan. The property is currently 98% occupied, with nine tenants, including ground-floor anchors Proxi and Sepia-two Michelin-starred dining establishments that recently renewed their leases for another five years with additional renewal options. This established retail presence ensures strong income stability for investors. Key Conversion Opportunity: Office to Multifamily Apartments This asset presents a compelling opportunity for an office-to-residential conversion, allowing investors to capitalize on the increasing demand for multifamily units in the West Loop. The property offers a phased approach to conversion: 43, 624 SF (72.8% of the building) can become available by the end of December 2024, providing the majority of the building for potential apartment conversion immediately after acquisition. An additional 1, 642 SF (2.7% of the building) will become available between March and November 2026 as leases expire, offering further flexibility for phased redevelopment. The final 5, 550 SF (9.2% of the building) will become available between January and April 2029 upon lease expirations, enabling investors to continue generating income from office leases while gradually converting spaces to residential use. Strategic Investment Potential This asset allows for a phased redevelopment strategy, maximizing cash flow while taking advantage of conversion opportunities as leases roll over. The property's prime location offers proximity to top-tier transportation, shopping, dining, and green spaces, making it highly attractive to prospective residential tenants. By converting the office floors to apartments, investors can tap into the strong rental market in the West Loop, while still benefiting from the stable income of long-term retail tenants. With strategic upgrades and a phased conversion plan, investors can elevate rental rates, attract premium residential tenants, and significantly enhance the property's value. The unique combination of historical architecture, Michelin-starred retail tenants, and conversion flexibility positions 565 W. Randolph St as a standout investment in one of Chicago's most sought-after neighborhoods.