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$600,000 Contingent

  • For Sale
  • Contingent
  • Multi-Family
  • 5 Total Beds
  • 3 Car Garage
  • Updated 1 day ago
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Classic Chicago charm meets an unbeatable Rogers Park location at 7529 N. Winchester. This handsome brick two-flat sits on an oversized lot and offers spacious layouts filled with vintage character, hardwood floors, and abundant natural light. A full basement provides additional living and storage space, while the detached garage and expansive backyard offer endless possibilities for entertaining, gardening, or relaxing outdoors. Nestled on a quiet tree-lined street, you'll enjoy easy access to parks, beaches, restaurants, shopping, and public transportation. Just minutes from Loyola University, downtown Evanston, and Lake Michigan, this is a fantastic opportunity for owner-occupants and investors alike. Experience the best of city living in one of Chicago's most vibrant and diverse neighborhoods. Roof (2021), Windows (2018), Back Porch Siding (2026), HWH (2022).

Full Property Details for 7529 N Winchester Ave

General

  • Price: $600,000
  • Taxes: $7,648 (2024)
  • Status: Contingent
  • Type: Multi-Family
  • Source: MRED
  • MLS ID: 12683557
  • Updated: 6/30/2026
  • Added to Site: 13 day(s) ago

Rental Information

  • Complex Features: Park, Curbs, Sidewalks, Street Lights, Street Paved

Interior

  • Basement: Finished, F

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Upper - Full Baths: 3

Bedrooms

  • Total Bedrooms: 5

Additional Information

  • Equipment: Ceiling Fan(s)
  • Other Features: Commuter Bus, Commuter Train

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 3
  • Parking Features: Garage Door Opener, Yes, Garage Owned, Detached, Garage

Location

  • Area: CHI - Rogers Park
  • County: Cook
  • Township: Rogers Park
  • Driving Directions: Rogers Ave to Winchester Ave - North to property

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299

Heating & Cooling

  • Heating Type: Natural Gas, Steam, Radiator(s)

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Construction: Vinyl Siding, Brick
  • Exterior Const.: Vinyl Siding, Brick
  • Basement: Yes
  • Basement Desc.: Finished, Full
  • Windows: Screens
  • Year Built: 1911
  • Built Before 1978: Yes

Unit Information

  • Units in Building: 2

Additional Structures

  • Other Structures: Shed(s)

Lot Features

  • Lot Size (Acres): 0.12
  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 35 x 150
  • Zoning: MULTI

Financial Considerations

  • Parking Included: Yes
  • Assessment Year: 1911
  • Tax Amount: $7,648.82
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 11304010070000

Listed by Redfin Corporation

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Listing agent

— 7529 N Winchester Ave —

  • Redfin Corporation

(312) 313-9229

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 7529 N Winchester Ave

School District:Chicago Public School District 299
NameGradesDistance
Jordan Elementary Community School
7414 North Wolcott Avenue, Chicago, IL 60626
PK-80.1 mi
Sullivan High School, Chicago, IL
6631 North Bosworth Avenue, Chicago, IL 60626
9-121.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 7529 N Winchester Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/25/2026
Listed
$600,000
26.32%
MLS
9/20/2005
Sold
$475,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 7529 N Winchester Ave

Year
Property Taxes
Change
Tax Assessment
Change
2023
$5,704
—
$44,001
33%
2023
$5,704
3%
$33,000
—
2022
$5,521
2%
$33,000
—
2021
$5,431
2%
$33,000
22%
2020
$5,313
-3%
$26,951
-12%
2019
$5,492
2%
$30,766
—
2018
$5,399
12%
$30,766
19%
2017
$4,840
3%
$25,859
—
2016
$4,679
10%
$25,859
—
2015
$4,258
28%
$25,859
26%
2014
$3,333
2%
$20,530
—
2013
$3,256
12%
$20,530
—
2012
$2,917
—
$20,530
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Redfin Corporation

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Listed by Curtis Hunt

7529 N Winchester Avenue, Chicago, IL 60626 (MLS# 12683557) is a Multi-Family property with 2 units containing 5 bedrooms and 0 full bathrooms. 7529 N Winchester Avenue is currently listed for $600,000 and was received on June 25, 2026. Want to learn more about 7529 N Winchester Avenue? Do you have questions about finding other Multi-Family real estate for sale in Rogers Park? You can browse all Rogers Park real estate or contact a Coldwell Banker agent to request more information.

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