5029 W Windsor Avenue Chicago, IL ^$ 799,000

5029 W Windsor Avenue

^$ 799,000

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5029 W Windsor Avenue

Chicago, IL, 60630

^$ 799,000

Bedrooms5 Baths4.0 Sq 2,900

Monthly Estimate*

^$ 5,045

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Single Family Home for sale in Chicago, IL

for $799,000 with 5 bedrooms and 4 full baths. This 2,900 square foot home was built in 1921.

Welcome to 5029 West Windsor Avenue, a stunning residence offering modern elegance and luxury throughout. This home features a striking dark exterior and chic white trim, opening to an expansive open-concept main floor with gleaning hardwood flooring and top-tier finishes. The chef's kitchen is a masterpiece, boasting pristine white cabinets and an island perfect for entertaining. Upstairs, the luxurious primary suite offers a serene retreat, followed by beautifully renovated bathrooms. The finished lower level expands the living space, and the outdoor patio boasts a spacious deck, a generous backyard, and a brand new long concrete driveway leading to a detached garage.

Single Family Active

Price

^$ 799,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 8,867

Style

Year Built

1921

Town/City

Chicago

County/Region

Cook

MLS | Web ID

12693284

Features

General

Living Area 2900

Sewer Public Sewer

Heating Natural Gas Forced Air

Cooling Central Air

Possession Closing

Appliances Range Refrigerator Washer Dryer

Garage Spaces 2

Association Fee Includes None

Construction Materials Brick

Year Built 1921

Township Jefferson

Tax Year 2023

Ownership Fee Simple

Assoc Fee Paid Per Not Applicable

County Cook

New Construction N

Property Type Residential Detached Single

Total Rooms 9

Full Baths 4

Status New

Directions West of 90 on Lawrence Avenue to North on Milwaukee to West Windsor Avenue to property

High School Schurz High School

City Chicago

High School District 299

MLS Area CHI - Portage Park

Elementary School Portage Park Elementary School

Tax Annual Amount 8867

Additional Parcels Y/N N

Standard Status Active

Middle/Junior School District 299

Elementary School District 299

Interior

Interior Amenities 1st Floor Bedroom 1st Floor Full Bath Separate Dining Room Pantry

Basement Finished Exterior Entry Full

Flooring Hardwood

Half Baths 0

Total Bedrooms 4

Room Type Bedroom 5

Total Baths 4

Bedrooms Possible 5

Exterior

Parking Features Concrete No Garage Yes Garage Owned Detached Garage

Water Source Lake Michigan

Total Parking 2

Lot Dimensions 35 X 126 X 35 X 126

Waterfront Y/N N

* Excluded Features

List By

Sky High Real Estate Inc.

Broker

Whbeaskar@yahoo.com

Affordability Calculator

$5,784

Per Month

Monthly Principal & Interest: $5,045
Monthly Property Taxes: $739
Monthly Home Insurance: --

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Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Single family listings in Chicago, IL

Average List Price ^$593,313

Percent of Sale Price 26%

About Chicago, IL

2,755,380 Population

-4% Since 2002

^$53,088 Median Income

36.07 Median Age

25% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

1539711 Elementary School

566846 Middle School

Schurz High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
7/1/2026	$799,000		Listed Price

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5029 W Windsor Avenue, Chicago, IL, 60630 is a Single Family Home for sale at $799,000 with 2,900 sqft. 5029 W Windsor Avenue has 5 bedrooms, 4.0 baths, and was built in 1921. The property's zip code is 60630 which is in Chicago, IL

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Weichert Realtors are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Data is updated as of 7/2/2026.

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5029 W Windsor Avenue

Single Family Home for sale in Chicago, IL

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