5545 S Winchester Ave
Nothing on record for this building in the last seven years, but our model still flags a rising risk of maintenance problems in the next 12 months. That forecast comes from the owner's wider portfolio and the surrounding area, not from this building's own record — treat it as a reason to ask questions, not as evidence of a problem. 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 Englewood average of 2.9.
The bar and the rating point different ways because they measure different things: the bar counts building violations already on file, the rating forecasts the next 12 months.
What's in the 5545 S Winchester Ave report
| Units | 5 |
|---|---|
| Year built | 1919 |
| Stories | — |
| Building area | 4,256 sq ft |
| Property class | 212 |
| PIN (Cook County parcel) | 20182010190000 |
Registered owner per Cook County Assessor records.
Landlord portfolio
Other Chicago properties this owner holds, with a risk rating for each.
Unlock complete reportThe five-unit residential building at 5545 S Winchester Ave in Englewood, owned by H.E. Harris, was constructed in 1919 and has generated a modest number of service requests over the past seven years. The most recent activity includes multiple tree-related issues in 2026, with two open inspection requests for tree removal and one closed request for tree debris cleanup. Prior to this, the property experienced some concerning maintenance issues, including a water-in-basement complaint in May 2026 and a rodent-related complaint in November 2024, both of which were resolved. Another tree removal inspection was addressed and closed in November 2024, suggesting ongoing challenges with tree maintenance on the property. While the building's service request history is relatively limited with only eight recorded incidents in the past seven years, the recent clustering of tree-related issues and the water and pest problems in 2024-2026 warrant attention to the property's maintenance patterns.
AI-generated · may contain errors · check the source data tables below
How 5545 S Winchester 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 4934 buildings in this neighborhood, 4095 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.
5545 S Winchester Ave apartment reviews
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5545 S Winchester Ave event timeline
Building violations, environmental complaints and enforcement, permits, scofflaw listings, and 311 calls — most recent records in order.
See all 3 events
Full history back to 2024 — violations, complaints, permits, and 311 calls.
Unlock complete timelineFull data for 5545 S Winchester 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.
| SR # | Created | Type | Department | Status |
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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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Unlock complete reportHow 5545 S Winchester Ave compares to the neighborhood
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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