565 W. Randolph St Chicago | West Loop Office-to-Residential Conversion Opportunity

565 W Randolph St, Chicago, IL, Chicago Illinois, 60661

Listing ID: CL-Illinois-28375 Commercial Office Building Office space
Published on: Monday, August 31, 2026 | Updated on: Monday, August 31, 2026

Listing Summary

Explore 565 W. Randolph St, a ±59,981 SF historic Class C office building featuring ground-floor Michelin-starred anchor retail (Proxi and Sepia) in Chicago's vibrant West Loop. Currently 98% occupied with stable income, this prime asset offers an exceptional value-add office-to-apartment conversion strategy with phased lease expirations through 2029.

Full Description

Capitalize on one of Chicago's premier investment offerings with 565 W. Randolph St, a ±59,981 SF historic asset built in 1872 located in the heart of the dynamic West Loop neighborhood. Combining timeless historical architecture with operational utility—including passenger and freight elevators—this property delivers a reliable income stream alongside immense redevelopment potential.

Key Investment Highlights

  • Anchor Retail Income: Anchored by ground-floor tenants Proxi and Sepia, two renowned Michelin-starred dining establishments that recently renewed their leases for an additional five years, ensuring robust, long-term cash flow.

  • High Occupancy: The building is currently 98% occupied across nine tenants, providing immediate stability while executing a strategic business plan.

  • West Loop Location: Positioned in Chicago's most sought-after market, offering tenants unmatched proximity to premier public transit, world-class dining, shopping, and urban green spaces.

Phased Office-to-Apartment Conversion Strategy

Designed for flexible, phased redevelopment, the property allows investors to tap into the high-demand multifamily rental market while maintaining ongoing revenue:

  • Phase 1: $\pm 43,624\text{ SF}$ ($72.8\%$ of the building) available by late 2024 for immediate residential conversion.

  • Phase 2: $\pm 1,642\text{ SF}$ ($2.7\%$) opening up between March and November 2026.

  • Phase 3: $\pm 5,550\text{ SF}$ ($9.2\%$) rolling over between January and April 2029, allowing continued office income during early redevelopment phases.

Position your portfolio for capital appreciation by transforming upper-level office space into luxury apartments while anchoring your investment with Michelin-grade retail stability in Chicago.

Quick Glance

  • Listing ID: CL-Illinois-28375
  • Status: Active
  • Year Build: 1872
  • Building Size: 59,981 SqFt
  • Lot Size: 59,981.00 SqFt

Property Documents

No documents available.

Complete Details

  • Year Build: 1872
  • Building Size: 59,981 SqFt
  • No of Stories: 6
  • Total Lot Area: 59,981.00 SqFt
  • Heating and Cooling: Not Specified
  • Building Class: Class C
  • Occupancy: 98

Pricing Details

Additional Features

Other Uses
  • Investment Type: Redevelopment
  • Zoning DX-7
  • Sub Type Traditional Office
Highlights
  • Prime West Loop Location: Positioned in Chicago's premier neighborhood, surrounded by top-tier dining, shopping, and mass transit options.
  • Office-to-Residential Conversion: A high-demand multifamily redevelopment opportunity designed to capitalize on Chicago's booming residential rental market.
  • Michelin-Starred Retail Anchors: Currently 98% occupied, featuring ground-floor anchors Proxi and Sepia with renewed 5-year leases providing stable income.
  • Phased Redevelopment Timeline: $\pm 43,624\text{ SF}$ ($72.8\%$) available for immediate apartment conversion, with subsequent roll-overs in 2026 and 2029 to maintain steady cash flow.
  • Value-Add Upside: Combines secure near-term retail cash flow with long-term residential conversion potential to maximize asset value.
Features
  • Historic Class C Building ($\pm 59,981\text{ SF}$): Built in 1872, blending timeless architectural character with modern amenities like passenger and freight elevators.
  • Vertical Transportation: Equipped with both a dedicated passenger elevator and a freight elevator

Listing Location

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