5458 W Windsor Avenue
Chicago, IL, 60630
$399,900
3 Beds
2 Baths
1,513 SqFt
0 Acres
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$399,900
5458 W Windsor Avenue
Chicago, IL, 60630
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Estate Sale – Incredible Opportunity in Jefferson Park! This spacious 3-bedroom, 2-bath home offers timeless character, solid bones, and endless potential for the right buyer. Situated on a generous lot with a detached 2-car garage, the property features a welcoming front porch, large room sizes, high ceilings, a full basement, and ample storage throughout. The second floor offers generously sized bedrooms and a full bath, while the unfinished basement provides additional space for future expansion or customization. Lovingly maintained over the years, this home is ready for its next chapter. Whether you’re a savvy investor, rehabber, or owner-occupant looking to build equity, this is a rare opportunity to renovate and create your dream home in a highly desirable Chicago neighborhood. Conveniently located near parks, schools, shopping, dining, public transportation, and major expressways. Estate sale. Property is being sold strictly AS-IS. Buyer to assume responsibility for any city requirements, if applicable. Bring your vision and unlock the tremendous potential this property has to offer! Multiple offers received. Highest and best due by Tuesday (06/09/26) at 6 PM

Property Details

Price:
$399,900
MLS #:
MRD12669441
Status:
Active Under Contract
Beds:
3
Baths:
2
Type:
Single Family
Neighborhood:
chiportagepark
Listed Date:
Jun 5, 2026
Finished Sq Ft:
1,513
Year Built:
1906
Chi – Portage ParkChiportagepark

Schools

School District:
299

Interior

Appliances
Range, Refrigerator
Bathrooms
2 Full Bathrooms
Cooling
Wall Unit(s)
Heating
Natural Gas

Exterior

Construction Materials
Vinyl Siding
Garage Spaces
2
Parking Features
Concrete, Garage Door Opener, Yes, Detached, Garage
Parking Spots
2
Parking Total
2
Roof
Asphalt

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2024
Taxes
$6,100
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Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

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Current real estate data for Single Family in Chicago as of Jun 26, 2026
2,782
Single Family Listed
68
Avg DOM
238
Avg $ / SqFt
$581,415
Avg List Price

Community

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Property Summary

    5458 W Windsor Avenue Chicago IL is a Single Family for sale in Chicago, IL, 60630. It is listed for $399,900 and features 3 beds, 2 baths, and has approximately 1,513 square feet of living space, and was originally constructed in 1906. The current price per square foot is $264. The average price per square foot for Single Family listings in Chicago is $238. The average listing price for Single Family in Chicago is $581,415. To schedule a showing of MLS#mrd12669441 at 5458 W Windsor Avenue in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
5458 W Windsor Avenue
Chicago, IL