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$799,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 2,900 Sq. Ft.
  • 2 Car Garage
  • Updated 19 hours ago

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Open House: 11:00 AM - 2:00 PM

Saturday 7/11 11:00 AM - 2:00 PM

5029 W Windsor Avenue,Chicago, IL 60630

5029 W Windsor AvenueChicagoIL60630

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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 for 5029 W Windsor Ave

General

  • Price: $799,000
  • Taxes: $8,867 (2023)
  • Status: Active
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12693284
  • Updated: 7/6/2026
  • Added to Site: 6 day(s) ago

Interior

  • Basement: Finished, E
  • 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
  • Township: Jefferson
  • Driving Directions: West of 90 on Lawrence Avenue to North on Milwaukee to West Windsor Avenue to property

School Information

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

  • Sewer: Public Sewer
  • Water: Lake Michigan

Structural Information

  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • 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: $8,867
  • Tax Year: 2023
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 13162180250000

Listed by Sky High Real Estate Inc.

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— 5029 W Windsor Ave —

  • Sky High Real Estate Inc.

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NMLS#: 1598647

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

Schools serving 5029 W Windsor Ave

School District:Chicago Public School District 299
NameGradesDistance
Portage Park Elementary School
5330 West Berteau Avenue, Chicago, IL 60641
PK-80.6 mi
Schurz High School
3601 North Milwaukee Avenue, Chicago, IL 60641
9-121.4 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/01/2026
Listed
$799,000
148.14%
MLS
5/02/2024
Sold
$322,000
—
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 5029 W Windsor Ave

Year
Property Taxes
Change
Tax Assessment
Change
2023
$8,867
—
$55,790
33%
2023
$8,867
3%
$42,000
—
2022
$8,644
2%
$42,000
—
2021
$8,451
34%
$42,000
49%
2020
$6,304
1%
$28,282
-9%
2019
$6,248
2%
$31,080
—
2018
$6,143
-6%
$31,080
2%
2017
$6,532
7%
$30,328
—
2016
$6,078
9%
$30,328
—
2015
$5,561
23%
$30,328
5%
2014
$4,530
2%
$28,799
—
2013
$4,421
—
$28,799
—
2012
$4,404
—
$28,799
—
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 Sky High Real Estate Inc.

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5029 W Windsor Avenue, Chicago, IL 60630 (MLS# 12693284) is a Single Family property with 5 bedrooms and 4 full bathrooms. 5029 W Windsor Avenue is currently listed for $799,000 and was received on July 01, 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.

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