5349 W Winona Street Chicago, IL ^$ 519,900

5349 W Winona Street

^$ 519,900

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Recently Listed

Open House 10/18 11am - 2pm

5349 W Winona Street

Chicago, IL, 60630

^$ 519,900

Bedrooms4 Baths2.0

Monthly Estimate*

^$ 3,591

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Multi-Family Home for sale in Chicago, IL

for $519,900 with 4 bedrooms and 2 full baths. This home was built in 1925.

Fantastic 2 Flat that only needs some personal touches. Tenant in place on 2nd Fl. is month to month. Long time owner occupies 1st floor. The basement is fully unfinished. 2 Furnaces, water tanks, electrical boxes (100 amp) and gas meters. First floor has 3 bedrooms, HWFL's in 2 bedrooms, Living room, and Dining room! Stainless steel appliances! Dining room has crown molding. There is a spacious deck and 2 car garage! The 2nd floor has 1 bedroom and 1 bath with a large walk in closet, enclosed porch. Separate entrances! The Brickwork is in great condition. Flood control!!

Open House

10/18/2026 11:00 AM - 2:00 PM

5349 W Winona Street Chicago, IL

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Multi-Family Active

Price

^$ 519,900

Bedrooms

Full Bath

Property Type

Multi-Family

Taxes

^$ 6,267

Style

Bungalow

Year Built

1925

Town/City

Chicago

County/Region

Cook

MLS | Web ID

12664739

Features

Exterior

Model Brick Bungalow

Parking Features Garage Door Opener Yes Garage Owned Detached Garage

Water Source Lake Michigan

Total Parking 2

Foundation Details Concrete Perimeter

Lot Dimensions 30X125

Waterfront Y/N N

Other Equipment Ceiling Fan(s) Sump Pump Multiple Water Heaters

General

Sewer Public Sewer

Heating Natural Gas Forced Air Sep Heating Systems - 2+

Possession Closing

Roof Asphalt

Zoning MULTI

Garage Spaces 2

Architectural Style Bungalow

Construction Materials Aluminum Siding Vinyl Siding Brick

Year Built 1925

Township Jefferson

Tax Year 2024

Ownership Fee Simple

Community Features Curbs Sidewalks Street Lights Street Paved

County Cook

New Construction N

Property Type Residential Income Two to Four Units

Total Rooms 10

Status New

Directions Foster E or W to Long S to Winona and east to 5349

City Chicago

High School District 299

MLS Area CHI - Jefferson Park

Tax Annual Amount 6267

Additional Parcels Y/N N

Standard Status Active

Middle/Junior School District 299

Elementary School District 299

Interior

Basement Unfinished Exterior Entry 8 ft + pour Concrete Full

Total Bedrooms 4

Room Type Kitchen Enclosed Porch

Total Baths 2

Bedrooms Possible 4

Bathroom Soaking Tub

Full Baths Building 2

Half Baths Building 0

Total Number of Units 2

* Excluded Features

List By

Timothy A. Witkowski

Broker

highenergybroker@aol.com

Affordability Calculator

$4,113

Per Month

Monthly Principal & Interest: $3,591
Monthly Property Taxes: $522
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 7.375% 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

Multi-family listings in Chicago, IL

Average List Price ^$644,790

Percent of Sale Price 24%

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.

566059 Elementary School

566846 Middle School

Unknown High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
10/16/2026	$519,900		Listed Price

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5349 W Winona Street, Chicago, IL, 60630 is a Multi-Family Home for sale at $519,900. 5349 W Winona Street has 4 bedrooms, 2.0 baths, and was built in 1925. 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 7.375% 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 10/17/2026.

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5349 W Winona Street

Multi-Family Home for sale in Chicago, IL

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