32-Unit Apartment Building Listed for Sale in Uptown Chicago

CHICAGO, ILLINOIS — Chicago-based multifamily brokerage firm Essex Realty Group, LLC has been exclusively engaged to market for sale 5022–5030 N. Winthrop Avenue, a renovated 32-unit courtyard-style apartment building located in the heart of Chicago’s historic Uptown neighborhood. The offering is listed for $9,472,000.

Property Overview: 32-Unit Apartment Building in Uptown

The property consists entirely of spacious two-bedroom apartments with expansive floor plans and highly desirable layouts. All residences have been modernized with attractive kitchens and bathrooms, in-unit laundry, and individual HVAC systems. Historically, the property has maintained consistently strong occupancy, reflecting sustained tenant demand and the ability to command premium rental performance.

The property is currently offered at a gross rent multiplier of 10x and an in-place cap rate of 6.54%, providing investors with stable cash flow and long-term appreciation potential.

Investment Opportunity for Chicago Multifamily Investors

Principal Steve Livaditis has been exclusively engaged in marketing the property on behalf of the ownership.

“This is an exceptionally well-maintained property in one of the city’s most rapidly transforming neighborhoods. Significant public investment, including the renovated Argyle CTA Station, expanded greenways, and extensive streetscape improvements, continues to strengthen the long-term tenant base and rental demand,” said Principal Steve Livaditis.

The combination of renovated interiors, strong in-place occupancy, and stable cash flow presents investors with an opportunity to acquire a well-positioned multifamily asset in one of Chicago’s most dynamic North Side neighborhoods.

Broker Representation for the Uptown Apartment Building Listing

Essex Realty Group is exclusively representing the ownership in the marketing and sale of 5022–5030 N. Winthrop Avenue.

The offering highlights continued investor demand for renovated apartment buildings with strong operational performance and long-term rental growth potential throughout Chicago’s North Side.

Uptown Multifamily Investment Market

Ideally situated just steps from the newly renovated CTA Red Line station, the property benefits from immediate access to Uptown’s vibrant entertainment, cultural, and neighborhood amenities, including the Aragon Ballroom, Riviera Theatre, the historic Uptown Theatre, and TimeLine Theatre’s new permanent home.

Residents also enjoy convenient access to Foster Beach, Montrose Beach, the Lakefront Trail, and downtown Chicago, positioning the property to capitalize on continued demand for transit-oriented and lakefront living.

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About Essex Realty Group, LLC

Essex Realty Group, LLC is a leading Chicago multifamily brokerage firm specializing in the sale of apartment buildings throughout the Chicago metropolitan area. The firm’s experienced brokers provide investment sales advisory services for private investors, institutions, and property owners across the region.