4344 N Winchester Chicago
This building has a substantial enforcement record over the last seven years, and our model sees a moderate chance of more in the next 12 months. Read the records below before you sign. Ask which issues were resolved, get repair commitments in writing, and inspect the unit yourself.
This building has 4 building violations (7y), above the North Center average of 0.5.
What's in the 4344 N Winchester Chicago report
| Units | 32 |
|---|---|
| Year built | 1907 |
| Stories | — |
| Building area | — |
| Property class | 315 |
| PIN (Cook County parcel) | 14184000180000 |
Registered owner per Cook County Assessor records.
Landlord portfolio
Other Chicago properties this owner holds, with a risk rating for each.
Unlock complete reportThe building at 4344 N Winchester in Chicago's North Center neighborhood is a 32-unit, 116-year-old property currently owned by R & D PROPERTIES. The most recent and significant issues occurred in early 2025, when the building underwent multiple complaint-driven inspections that resulted in four building code violations, though these were promptly resolved. The building's service request history over the past seven years shows a total of ten incidents reported through the 311 system, with the most recent being a pothole complaint in March 2026. The variety of service requests includes two recycling inspection requests and a water-related issue in February 2025, as well as an injured animal report in August 2025 and a plumbing violation report from December 2024. Notably, there has been only one building permit recorded in the past seven years, though this could be due to the building's historical status requiring fewer modifications. While the recent building code violations are concerning, it's worth noting that they were resolved in the same month they were issued.
AI-generated · may contain errors · check the source data tables below
How 4344 N Winchester Chicago'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 2652 buildings in this neighborhood, 2493 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.
4344 N Winchester Chicago apartment reviews
Real experiences from people who have lived here. Share yours to help other renters decide.
Share your experience — Help other renters by leaving an honest apartment review
Loading reviews…
4344 N Winchester Chicago event timeline
Building violations, environmental complaints and enforcement, permits, scofflaw listings, and 311 calls — most recent records in order.
See all 7 events
Full history back to 2022 — violations, complaints, permits, and 311 calls.
Unlock complete timelineFull data for 4344 N Winchester Chicago 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.
| Violation # | Date | Category | Status | Address |
|---|---|---|---|---|
| Loading… | ||||
What this is
Violations issued for failure to register or maintain a vacant or abandoned building.
| Docket # | Violation # | Issued | Department | Type | Disposition | Total Fines |
|---|---|---|---|---|---|---|
| Loading… | ||||||
What this is
Building permits issued by the City of Chicago for new construction, alterations, and repairs at this parcel.
| Permit # | Issued | Status | Description |
|---|---|---|---|
| Loading… | |||
What this is
Chicago 311 service requests recorded at this parcel — maintenance complaints and quality-of-life requests.
| SR # | Created | Type | Department | Status |
|---|---|---|---|---|
| Loading… | ||||
What this is
Environmental complaints filed about this property with the City of Chicago.
| Complaint # | Date | Type | Inspector | Resolution | Resolved |
|---|---|---|---|---|---|
| Loading… | |||||
What this is
Formal environmental enforcement cases brought against this property.
| Case # | Date | Type | Violation | Disposition | Status | Fine |
|---|---|---|---|---|---|---|
| Loading… | ||||||
Affordable Rental Housing requires a full report
Included with every paid plan.
Unlock complete reportAsbestos & Demolition Notifications requires a full report
Included with every paid plan.
Unlock complete reportHow 4344 N Winchester Chicago compares to the neighborhood
This building against comparable properties in North Center. Toggle filters to narrow the peer group.
No comparable buildings found with the selected filters. Try removing a filter.
Look up the next apartment before you sign
Search any Chicago address free — no account needed to see the risk rating.
Get the complete picture
Every plan unlocks the complete report: all Chicago datasets, full history, landlord portfolio, and PDF & Excel exports.
Report Bundle
For the buildings you're deciding on right now
$10one time
3premium reports
$3.33 per report · charged once, never renews
Each credit unlocks one building's premium report for 30 days.
- 3 premium reports — AI executive summary included
- Live data across all 27 public record types
- 200 records per dataset
- PDF & Excel exports included
- Compare up to 10 buildings side-by-side
- Credits never expire until you use them
Apartment Hunter
For a wide search across many buildings
$39one time
30premium reports
$1.30 per report · charged once, never renews
Each credit unlocks one building's premium report for 30 days.
- 30 premium reports — AI executive summary included
- Live data across all 27 public record types
- 200 records per dataset
- PDF & Excel exports included
- Compare up to 10 buildings side-by-side
- Credits never expire until you use them
Renter
For the weeks when the stakes are highest
$8.33/mo
5premium reports / mo
Billed $100/year — save $44 vs monthly
Renews automatically until you cancel.
- Unlimited standard reports — 50 records per dataset
- 5 premium AI reports per month — live data, 200 records per dataset, all 27 record types
- PDF & Excel exports on every report
- Compare up to 10 buildings side-by-side
- Full event timeline — every year of history
- Landlord portfolio & ownership insights
Less than $0.28/day. Cancel anytime.
Cancel anytime · Data sourced from the City of Chicago Department of Buildings, Chicago 311, Cook County Assessor & the Chicago Data Portal