Real Estate Agent Teresa Shreve
Teresa Shreve
(815) 289-3362
Rockford
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5037 W Winona Street, Chicago, IL 60630

$599,999
  • 5037 W Winona Street, Chicago, IL 60630 Main Photo

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Active
BEDS3 BATHS3 full MLS#12584323
STATUSActive PROPERTY TYPEMulti Unit - Multiple SUBDIVISIONForest Glen SCHOOLDistrict 299

Property Description

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.

5037 W Winona Street | MLS# 12584323

This multi-family property located at 5037 W Winona Street, Chicago, IL 60630 is currently listed for sale with an asking price of $599,999. W Winona Street is located within the District 299 school district. Search Chicago real estate on tshreve.gogambino.com today.

Upcoming Open Houses

Open House Saturday April 25th, 11:00am - 1:00pm

Property Features

Property Type: Multi Unit - Multiple
Basement: Finished, Exterior Entry, Concrete, Storage Space, Full
Basement: Yes
Garage: 2
Heating: Natural Gas, Forced Air
Lot Size: 0.09 Acres
Roof Type: Asphalt
Taxes: $6,756
Year Built: 1917

Feature Descriptions

Additional rooms: Kitchen, Enclosed Porch
Additional Structures: Garage(s)
Exterior: Aluminum Siding
Lot Dimensions: 31X126
Other Equipment: CO Detectors, Ceiling Fan(s)
Parcel#: 13094060080000
Parking: Garage Door Opener, Yes, Garage Owned, Detached, Garage
Sewer: Public Sewer
Total Rooms: 16
Township: Jefferson
Water: Lake Michigan

Local Schools

School District: District 299

Listed By / Shown By

Listed By

Agency Name: Option Premier LLC
Agency Phone: 312-500-5808

Shown By

Agent Name: Teresa Shreve
Agent Phone: (815) 289-3362
Agency Title: Gambino Realtors

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Estimated Payment

$ 3,463.39 per month $2,725.39 Principal & Interest $563.00 Property Tax $175.00 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 04/24/2026. The listing information on this page last changed on 04/24/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 04/24/2026 12:00:46 AM EST) or MRED MLS (last updated Thu 04/23/2026 11:58:08 PM EST) or Rockford Board of Realtors (NWIAR) (last updated Thu 04/23/2026 10:15:31 PM EST) or Northern Illinois Commercial Association Realtors (last updated Thu 04/23/2026 2:10:09 PM EST). Real estate listings held by brokerage firms other than Gambino Realtors may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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