5037 W Winona Street Chicago, IL $ 599,999
5037 W Winona Street
$ 599,999
Open House 3/28 11am - 1pm
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5037 W Winona Street

Chicago, IL, 60630
$ 599,999
Bedrooms3 Baths3.0

Monthly Estimate*

$ 3,694

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Multi-Family Home for sale in Chicago, IL

for $599,999 with 3 bedrooms and 3 full baths. This home was built in 1917.

Excellent opportunity to own a well-maintained 2-flat in the highly desirable Jefferson Park neighborhood, offering strong rental potential and an ideal setup for owner-occupants. This classic Chicago multi-unit features two spacious units, a finished basement, and shared laundry, making it a versatile investment in one of the city's most commuter-friendly areas. The first-floor unit offers 2 bedrooms and 1 bathroom with hardwood floors throughout, a bright and spacious living room that flows into a separate dining room, and a well-appointed kitchen with an eat-in breakfast area. This unit also includes central heating and air conditioning, providing year-round comfort. The second-floor unit features 1 bedroom and 1 bathroom with 9-foot ceilings. All wood floors throughout the first/Second floor. The layout includes a large living room, separate dining room, and a spacious kitchen with a walk-in pantry, along with a generous bedroom featuring a large walk-in closet. The finished basement offers additional living, recreation, or storage space and includes shared laundry and mechanicals, including the furnace, A/C, and water heater. Significant exterior improvements include a newer roof, windows, siding, garage, concrete patio, and privacy fence, creating a low-maintenance investment with appealing outdoor space. Located in the heart of Jefferson Park, the property offers exceptional access to transportation and neighborhood amenities, including nearby **CTA Blue Line stations and multiple Metra lines for easy commuting to downtown Chicago. Residents are also within walking distance to everyday conveniences such as Mariano's, Target, and Starbucks, with quick access to Interstate 90 and Interstate 94. Jefferson Park is known for its strong rental demand, neighborhood charm, and unmatched transit connectivity, making this property an excellent choice for investors seeking steady income or buyers looking to live in one unit while generating rental income from the other.

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Open House

3/28/2026 11:00 AM - 1:00 PM
5037 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

$ 599,999

Bedrooms

3

Full Bath

3

Property Type

Multi-Family

Taxes

$ 6,756

Style

Year Built

1917

Town/City

Chicago

County/Region

Cook

MLS | Web ID

12584323

Features
General
Sewer Public Sewer
Heating Natural Gas Forced Air
Possession Closing
Roof Asphalt
Zoning MULTI
Garage Spaces 2
Construction Materials Aluminum Siding
Year Built 1917
Township Jefferson
Tax Year 2023
Ownership Fee Simple
Community Features Park Curbs Sidewalks Street Lights Street Paved
County Cook
New Construction N
Property Type Residential Income Two to Four Units
Subdivision Name Forest Glen
Other Structures Garage(s)
Total Rooms 16
Status Active
Directions Foster to LeClaire (South) to Winona (East) to property.
City Chicago
High School District 299
MLS Area CHI - Forest Glen
Tax Annual Amount 6756
Additional Parcels Y/N N
Virtual Tour https://www.zillow.com/view-imx/7a88709f-4b5d-4cdd-939b-8271ec5693d8?wl=true&setAttribution=mls&initialViewType=pano
Standard Status Active
Middle/Junior School District 299
Elementary School District 299
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Interior
Basement Finished Exterior Entry Concrete Storage Space Full
Total Bedrooms 3
Room Type Kitchen Enclosed Porch
Total Baths 3
Bedrooms Possible 3
Full Baths Building 3
Half Baths Building 0
Total Number of Units 2
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Exterior
Exterior Amenities Breezeway Lighting
Parking Features Garage Door Opener Yes Garage Owned Detached Garage
Water Source Lake Michigan
Total Parking 2
Foundation Details Concrete Perimeter
Lot Dimensions 31X126
Waterfront Y/N N
Other Equipment CO Detectors Ceiling Fan(s)
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* Excluded Features
List By
Option Premier Llc

Broker

cory@optionpremier.com

Email

Affordability Calculator

$4,257
Per Month
87%
13%
0%
Monthly Principal & Interest
$3,694
Monthly Property Taxes
$563
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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
566059 Elementary School
566846 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
3/6/2026$599,999 Listed Price

Map


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5037 W Winona Street, Chicago, IL, 60630 is a Multi-Family Home for sale at $599,999. 5037 W Winona Street has 3 bedrooms, 3.0 baths, and was built in 1917. The property's zip code is 60630 which is in Chicago, IL