5321 N Winthrop Ave
Nothing on record for this building in the last seven years, and our model puts it at a low risk of maintenance problems over the next 12 months. No public enforcement record to go on. Walk the building, ask the current tenants how repairs get handled, and get any promises in writing.
This building has 0 building violations (7y), at or below the Edgewater average of 2.1.
What's in the 5321 N Winthrop Ave report
| Units | 3 |
|---|---|
| Year built | 1905 |
| Stories | — |
| Building area | 4,081 sq ft |
| Property class | 211 |
| PIN (Cook County parcel) | 14082080340000 |
Registered owner per Cook County Assessor records.
Landlord portfolio
Other Chicago properties this owner holds, with a risk rating for each.
Unlock complete reportThe three-unit residential building at 5321 N Winthrop Ave in Chicago's Edgewater neighborhood, owned by Larry A Boss, has been standing since 1905. In the past seven years, the property has generated a total of six service requests through the 311 system, with all issues documented as having been resolved. The most recent incident was a graffiti removal request filed in April 2026, following a pattern of service requests primarily related to external maintenance and utilities between 2025 and early 2026. These included two cable TV-related complaints (one in August 2025 and another in April 2025), a sewer cleaning inspection request (August 2025), a tree debris clean-up request (March 2025), and an inspection of the public way (January 2026). While the variety of service requests indicates ongoing maintenance and community engagement with municipal services, the fact that all reported issues have been resolved promptly is noteworthy.
AI-generated · may contain errors · check the source data tables below
How 5321 N Winthrop Ave's risk score is calculated
We trained a model on 7 years of Chicago code enforcement data — building violations, 311 complaint history, environmental enforcement, and owner track records. It estimates the probability that the City of Chicago will find a code violation at this address in the next 12 months. Lower % = safer.
What the score means for you
Lower risk — safer than most nearby
City inspectors rarely find violations here. Strong maintenance history and a clean complaint record.
Typical — about average for the neighborhood
Some past violations or complaints on record. Worth asking the landlord about any open issues before signing.
Higher risk — riskier than most nearby
Elevated violation and complaint history. City inspectors have found issues here before and are statistically likely to again.
Out of 1377 buildings in this neighborhood, 592 are predicted to be safer. The band is relative to this neighborhood, so a share of every neighborhood falls in each colour.
violation
likely
What's driving this score
The data points that most influenced this building's risk rating — ranked by the weight the model placed on each one.
5321 N Winthrop Ave apartment reviews
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5321 N Winthrop Ave event timeline
Building violations, environmental complaints and enforcement, permits, scofflaw listings, and 311 calls — most recent records in order.
Full data for 5321 N Winthrop Ave apartments
Chicago public datasets for this parcel — building violations, permits, 311 calls, environmental complaints and enforcement, scofflaw listings, and vacant building registrations.
What this is
Violations issued by the City of Chicago Department of Buildings against this parcel.
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What this is
Violations issued for failure to register or maintain a vacant or abandoned building.
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What this is
Building permits issued by the City of Chicago for new construction, alterations, and repairs at this parcel.
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What this is
Chicago 311 service requests recorded at this parcel — maintenance complaints and quality-of-life requests.
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What this is
Environmental complaints filed about this property with the City of Chicago.
| Complaint # | Date | Type | Inspector | Resolution | Resolved |
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What this is
Formal environmental enforcement cases brought against this property.
| Case # | Date | Type | Violation | Disposition | Status | Fine |
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Cancel anytime · Data sourced from the City of Chicago Department of Buildings, Chicago 311, Cook County Assessor & the Chicago Data Portal