5029 W Windsor Avenue, Chicago, IL 60630 - Photo 1

1/1

$780,000

Sold
Closed
Single Family
5 Beds
4 Full Baths
2,900 Sq. Ft.
2 Car Garage

1/1

Property Description

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.

Full Property Details

Full Property Details for 5029 W Windsor Ave

General

Sold For: $780,000
Taxes: $10,049 (2024)
Status: Closed
Type: Single Family
Source: MRED
MLS ID: 12693284
Added to Site: 96 day(s) ago

Interior

Interior Features: 1st-Floor Bedroom, 1st-Floor Bath, Separate Dining Room, Pantry
Appliances: Range, Refrigerator, Washer, Dryer
Flooring: Hardwood

Rooms

Bathrooms

Total Bathrooms: 4
Full Bathrooms: 4
Basement Baths: Yes

Bedrooms

Total Bedrooms: 5
Bedrooms(Blw Grade): 1

Parking

Garage: Yes
Garage Spaces: 2
Total Spaces: 2
Parking Features: Concrete, No Garage, Yes, Garage Owned, Detached, Garage

Location

Area: CHI - Portage Park
County: Cook
Driving Directions: West of 90 on Lawrence Avenue to North on Milwaukee to West Windsor Avenue to property

School Information

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

Community

Assoc. Fees Include: None

Heating & Cooling

Cooling Type: Central Air Conditioning
Heating Type: Natural Gas, Forced Air

Utilities

Water: Lake Michigan

Structural Information

Construction: Brick
Exterior Const.: Brick
Basement Desc.: Finished, Exterior Entry, Full
Sub-Flooring: Hardwood
Square Feet: 2,900
Sq. Ft. Source: Estimated
Year Built: 1921
Built Before 1978: Yes
Remodeled/Updated: 2026

Lot Features

Lot Size Range: Less than .25 Acre
Lot Dimensions: 35 x 126 x 35 x 126

Financial Considerations

Parking Included: Yes
Assessment Year: 1921
Tax Amount: $10,049.38
Tax Year: 2024

Disclosures and Reports

Ownership: Fee Simple
Property ID: 13162180250000

Listed by Sky High Real Estate Inc.
Sold by @properties Christie's International Real Estate

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— 5029 W Windsor Ave —

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Schools

Schools serving 5029 W Windsor Ave

School District:Chicago Public School District 299

Name	Grades	Distance
Portage Park Elementary School 5330 West Berteau Avenue, Chicago, IL 60641	PK-8	0.6 mi
Schurz High School 3601 North Milwaukee Avenue, Chicago, IL 60641	9-12	1.4 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 5029 W Windsor Ave

Date

Details

Price

Change

Source

8/28/2026

Sold

$780,000

-2.38%

MLS

7/01/2026

Listed

$799,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Active
Updated 4 days ago

1,750
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Beds
3
Total Baths
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Sq. Ft.

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Total Beds

5029 W Windsor Avenue, Chicago, IL 60630 (MLS# 12693284) is a Single Family property that was sold at $780,000 on August 28, 2026. Want to learn more about 5029 W Windsor Avenue? Do you have questions about finding other Single Family real estate for sale in Portage Park? You can browse all Portage Park real estate or contact a Coldwell Banker agent to request more information.

5029 W Windsor Ave Chicago, IL 60630