5029 W Windsor Avenue
Chicago, IL, 60630
$799,000
4 Beds
4 Baths
2,900 SqFt
0 Acres
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$799,000
5029 W Windsor Avenue
Chicago, IL, 60630
MLS #MRD12693284 image #0MLS #MRD12693284 image #1MLS #MRD12693284 image #2MLS #MRD12693284 image #3MLS #MRD12693284 image #4MLS #MRD12693284 image #5MLS #MRD12693284 image #6MLS #MRD12693284 image #7MLS #MRD12693284 image #8MLS #MRD12693284 image #9MLS #MRD12693284 image #10MLS #MRD12693284 image #11MLS #MRD12693284 image #12MLS #MRD12693284 image #13MLS #MRD12693284 image #14MLS #MRD12693284 image #15MLS #MRD12693284 image #16MLS #MRD12693284 image #17MLS #MRD12693284 image #18MLS #MRD12693284 image #19MLS #MRD12693284 image #20MLS #MRD12693284 image #21MLS #MRD12693284 image #22MLS #MRD12693284 image #23MLS #MRD12693284 image #24MLS #MRD12693284 image #25MLS #MRD12693284 image #26MLS #MRD12693284 image #27MLS #MRD12693284 image #28MLS #MRD12693284 image #29MLS #MRD12693284 image #30MLS #MRD12693284 image #31MLS #MRD12693284 image #32MLS #MRD12693284 image #33
Spectacular fully-renovated 5-bedroom, 4-bathroom residence delivering master-class craftsmanship and sophisticated modern design in a highly desirable Jefferson Park location. From the curb, the home makes a bold statement with its striking dark exterior contrasted by crisp white trim. Inside, a complete top-to-bottom transformation unfolds across an expansive, light-filled open-concept main floor, accented by gleaming hardwood flooring and premium finishes throughout. The custom chef’s kitchen serves as the home’s centerpiece, boasting pristine white cabinetry, high-end appliances, and an oversized entertainment island. Upstairs, the luxurious primary suite offers a serene, spa-inspired retreat, complemented by beautifully appointed bathrooms. The fully finished lower level dramatically expands your living space, ideal for a media room, home gym, or guest quarters. Step outside to a private outdoor oasis featuring a spacious deck, generous backyard, and a brand-new concrete driveway leading to a detached garage. Perfectly positioned for effortless city living, this home offers unbeatable location convenience just minutes from the Kennedy Expressway (I-90) and steps from the Jefferson Park Transit Center for seamless Blue Line and Metra access. True turn-key luxury.

Property Details

Price:
$799,000
MLS #:
MRD12693284
Status:
Active Under Contract
Beds:
4
Baths:
4
Type:
Single Family
Neighborhood:
chiportagepark
Listed Date:
Jul 1, 2026
Finished Sq Ft:
2,900
Year Built:
1921
Chi – Portage ParkChiportageparkPortage Park Elementary SchoolSchurz High School

Schools

School District:
299
Elementary School:
Portage Park Elementary School
High School:
Schurz High School

Interior

Appliances
Range, Refrigerator, Washer, Dryer
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Hardwood
Heating
Natural Gas, Forced Air
Interior Features
1st Floor Bedroom, 1st Floor Full Bath, Separate Dining Room, Pantry

Exterior

Construction Materials
Brick
Garage Spaces
2
Parking Features
Concrete, No Garage, Yes, Garage Owned, Detached, Garage
Parking Spots
2
Parking Total
2

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2024
Taxes
$10,049
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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 Jul 23, 2026
2,582
Single Family Listed
73
Avg DOM
235
Avg $ / SqFt
$557,038
Avg List Price

Community

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Property Summary

    5029 W Windsor Avenue Chicago IL is a Single Family for sale in Chicago, IL, 60630. It is listed for $799,000 and features 4 beds, 4 baths, and has approximately 2,900 square feet of living space, and was originally constructed in 1921. The current price per square foot is $276. The average price per square foot for Single Family listings in Chicago is $235. The average listing price for Single Family in Chicago is $557,038. To schedule a showing of MLS#mrd12693284 at 5029 W Windsor Avenue in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
5029 W Windsor Avenue
Chicago, IL