5738 W Windsor Ave

Chicago, IL 60630

$659,000
Price
8
Beds
—Sq. Ft.
— / Sq. Ft.
—
Sq. Ft.
—
per Sq. Ft.
a house view with a garden space
a front view of a house with garden
a view of house with yard
a view of yard
a view of a house with a garage and a fireplace
a front view of a house with garden

Description

The neighborhoods of Portage Park, and Jefferson Park, 2-unit brick building offering a concrete driveway into your large 2-car garage with great curb appeal, individual utilities, each floor has 3-bedrooms, 1-bath, with the basement being 2-bedrooms, 1-bath. 2020 newer roof. Basement gas and ComEd including electric Space heat connected to 1st floor unit within Walking distance to Milwaukee Ave., and Central Ave., and within short distance and easy access to public transportation of CTA Blue line,...The neighborhoods of Portage Park, and Jefferson Park, 2-unit brick building offering a concrete driveway into your large 2-car garage with great curb appeal, individual utilities, each floor has 3-bedrooms, 1-bath, with the basement being 2-bedrooms, 1-bath. 2020 newer roof. Basement gas and ComEd including electric Space heat connected to 1st floor unit within Walking distance to Milwaukee Ave., and Central Ave., and within short distance and easy access to public transportation of CTA Blue line, Jefferson memorial Park, Wilson Park, shops, restaurants, daily life necessities, and within minutes to major roads, and interstates. This is 2 Units not 3 Units. Per sellers request buyers pre-approval required before interior access.

Property Details for 5738 West Windsor Avenue

Area
CHI - Portage Park
Township
Rogers Park
Ownership
Fee Simple
Num Of Garage Spaces
2.0
Num Of Parking Spaces
2.0
Parking Included in Price
Yes
Heat/Fuel
Natural Gas, Forced Air
Zoning
MULTI
LISTING UPDATED: 12/04/2025 02:01 PM

Property Details for 5738 West Windsor Avenue

StatusActive
MLS #12506910
Days on Market46
Taxes$7,740 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeTwo to Four Units / 2 Flat
Year Built1922
Lot Size0.11 AC / 4,625 SF
CountyCook County

Location

Listing Courtesy of Century 21 Circle
Add your commute

Building Information for 5738 West Windsor Avenue

Stories-Residences2Year Built1922Building Size-Lot Size0.11 AC / 4,625 SF

Payment Calculator

$3,901 per month

30 year fixed, 6.28% Interest

Principal and Interest

$3,256

Property Taxes

$645

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 5738 West Windsor Avenue

General Information
School Information
  • Elementary School District: 299
  • Elementary School: Beard Elementary School
  • Jr High Middle School: Prussing Elementary School
  • High School District: 299
  • High School: Taft High School
  • Middle Or Junior School District: 299
Addtl Parking Information
  • Parking Details: Yes, Garage Owned, Detached, Garage
Property Information
Interior Features
  • Num Of Rooms: 15
  • Bedrooms Total: 8
  • Bedrooms (Below Grade): 0
  • Basement Type: Finished, Full
  • Bedrooms Possible: 8
  • Basement Bathrooms: No
  • # Full Baths in Building: 3
  • # Half Baths in Building: 0
  • Num of Baths: 3.0
Exterior Features
  • Patio And Porch Features: Patio
Utilities / Equipment
  • Sewer: Sewer-Public
  • Water: Public
Property/Lot Information
  • New Construction YN: No
  • Rebuilt: No
  • Rehabilitated: No
  • Built Before 1978: Yes
  • Age: 100+ Years
  • Lot Size: Less Than .25 Acre
  • Lot Size Source: County Records
  • Lot Dimensions: 37x125
  • Total # Units in Building: 2.0
  • Waterfront: No
  • Construction: Brick
  • Foundation Details: Brick/Mortar
  • General Information: None
  • North Coordinate: 4530
  • South Coordinate: 0
  • East Coordinate: 0
  • West Coordinate: 3758
  • 3 Br Un In Bldg: Yes
  • Conversion: N
Property and Assessments
  • Public Document Count: 0
  • Photos Count: 6
  • Deconversion: N
  • OpenHouse Count: 0
Virtual Tour/Additional Media
  • Virtual Tour: None
  • Virtual Tour YN: No
Multi Family
Unit 1
  • Unit Type Actual Rent: $.00
  • Unit Type Baths Total: 1
  • Unit Type Beds Total: 3
  • Unit Type Type: Unit 1
  • Lease Expiration Date: N
Unit 2
  • Unit Type Actual Rent: $.00
  • Unit Type Baths Total: 1
  • Unit Type Beds Total: 3
  • Unit Type Type: Unit 2
  • Lease Expiration Date: N

Property History for 5738 West Windsor Avenue

DateEvent & SourcePriceAppreciation
Oct 31, 2025

Listed (Active)

MRED #12506910

$659,000—
DateEvent & SourcePrice
10/31/2025

Listed (Active)

MRED #12506910

$659,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 5738 West Windsor Avenue

Taxable ValueLand$12,073Additions$27,926Total$39,999
Tax Record2023$7,740 ($645 / month)
Home Facts
Baths2Total Finished SqFt2,464 SqFtAbove Grade Finished SqFt2,464 SqFtStories2Lot Size4,312 SqFtStyleMulti-Family Res (5+ Units)Year Built1922CountyCOOKAPN13-17-221-022

Schools near 5738 West Windsor Avenue

This home is within Chicago Public Schools.
Rating
School
Type
Grades
Distance
Prussing Elementary School
Public - K to 8
Taft High School
Public - 7 to 12
Vaughn Occupational High School
Public - 9 to 12
Rickover Naval Academy High School
Public - 9 to 12
Rating
School
Distance
Prussing Elementary School
PublicK to 8

Taft High School
Public7 to 12

Vaughn Occupational High School
Public9 to 12

Rickover Naval Academy High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 5738 West Windsor Avenue, Chicago, IL 60630

5738 West Windsor Avenue is a multi-family home for sale in Chicago, IL 60630. This property was listed for sale on October 31, 2025 by Century 21 Circle, it's currently listed at $659,000. This listing's school district is Chicago Public Schools. Nearby schools include Prussing Elementary School, Taft High School and Vaughn Occupational High School. 5738 West Windsor Avenue is a 8-bed, 3-bath, multi-family home built in 1922.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Century 21 Circle

Based on information from one of the following Multiple Listing Services: Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/04/2025 02:01 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.