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4 Beds
3 Baths

$569,999

5037 W Winona Street, Chicago IL, 60630

Built in1917
Property typeMulti-family
Listed by Cory Tanzer with Option Premier LLC 312-500-5808

Overview

Active

Listed Oct 2, 2026

Updated 17h ago

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. Unit 1 is empty perfect for owner occupancy, making rental income, ready now for you to move in. 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. Basement features full bedroom and bathroom. Significant exterior improvements include a newer roof, windows, siding, 2 car 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. Home has a 2 car garage and parking pad next to garage. Fully fenced in yard. Click on 3d tour to walk though unit. 1st floor unit availabe for owner occupancy now. Do not miss this chance to live and have others cover your mortage!

$3,792/mo

Est. mortgage payment based on a $569,999 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
12775522

Interior Features

Bedrooms
4
Bathrooms
3
Heating
Yes
Basement
Yes

Other Property Details

Taxes
$9,044
Tax Frequency
Annually
Garage
Yes
MLS provider logo

Listed by Cory Tanzer with Option Premier LLC 312-500-5808

The data relating to real estate for sale on this website comes in part from the Broker ReciprocitySM Program of Midwest Real Estate Data. Real estate listings held by brokerage firms other than The Wexler Gault Group are marked with the Broker ReciprocitySM logo or the Broker ReciprocitySM thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers.

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Data is refreshed every 3 hours. Listing last updated 8:06 AM UTC on 10/9/2026. 

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