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Commercial For sale Office space Office Building

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

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

$11,250,000
$188 / sq ft 3.91% cap rate Listed Aug 31, 2026
59,981 sqft
Building
59,981 sqft
Lot
1872
Built
6
Stories
Class C
Class

About this property

565 W. Randolph St Chicago | West Loop Office-to-Residential Conversion Opportunity is an office space for sale in Chicago, Illinois, listed at $11,250,000. Key details: year built 1872, building size 59,981 sqft, lot size 59,981 sqft, stories 6. Listed by Tony Hardy of Keller Williams ONEChicago on LoopingCloud and last updated August 31, 2026.

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.

Key highlights

  • Occupied
  • Investment Type Redevelopment
  • Zoning DX-7
  • Sub Type Traditional Office

Lending Opportunities

Connect with a mortgage professional to explore financing options and see what you may qualify for.

CompanyLender typeContactPhone
TheLoanProsTeam Mortgage Broker Roxanne Chung (754) 707-5877
Money Solutions, LLC Mortgage Broker Jennifer A. Judice (813) 431-5000

Property details

Key facts

Year Built
1872
Building Size
59,981 sqft
Lot Size
59,981 sqft
Stories
6
Building Class
Class C
Occupied
Yes
Occupancy
98%
Property Status
Normal Sale
Building Status
Existing

Pricing details

Net Operating Income
$439,360
Financing
Third Party Financing
Investment Property
Active investment property

Investment snapshot

3.91%
Cap rate
$439,360
Net operating income
$188
Price per sq ft

Acquisition options

OptionAsking priceCap rateCommissionMonthly incomeOwnership
Purchase Only $11,250,000 6% - - -

Features and amenities

Property Other Use Types

  • Investment Type: Redevelopment
  • Zoning DX-7
  • Sub Type Traditional Office

Property 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

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.

Location

Address as shown by the lister.

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About this area - Chicago

Population
4,382
Housing units
3,012
Land area
0.3 sq mi
County
Cook

Neighborhood

Places shown on the map come from Google Maps and are near the property. Check details with each place before you rely on them.

Documents, links and contacts

Links

2 links

Additional contacts

1 person to reach

Frequently asked questions

What is the asking price of 565 W. Randolph St Chicago | West Loop Office-to-Residential Conversion Opportunity?

565 W. Randolph St Chicago | West Loop Office-to-Residential Conversion Opportunity is listed at $11,250,000. That works out to about $188 per square foot. The stated cap rate is 3.91%.

Where is 565 W. Randolph St Chicago | West Loop Office-to-Residential Conversion Opportunity located?

The property is in 565 W Randolph St, Chicago, IL, Chicago, Illinois 60661, Cook County.

What type of property is this?

This is an office space for sale in the commercial category.

How big is the property?

The building is 59,981 sqft. The lot is 59,981 sqft.

Is financing available?

The lister indicates: Third Party Financing.

Who do I contact about this listing?

Tony Hardy of Keller Williams ONEChicago listed this property. Use the Request Info button to send a message or call (773) 575-6082.

When was this listing published?

It was published on August 31, 2026 and last updated on August 31, 2026.

Listing information

Listing ID
CL-Illinois-28375
Published
Aug 31, 2026
Last updated
Aug 31, 2026

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Disclaimer: LoopingCloud is a social listing portal that connects real estate professionals, service providers, buyers, and sellers. All property information, descriptions, availability, financial details, and any offerings are provided by the respective lister or service provider and are not independently verified by LoopingCloud.

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