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5037 W Winona St , Chicago, IL 60630
$569,999
Est. Payment: $3,058.31/mo
4 Bed
3 Bath
Status: contingent | Days on site: 22
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88528 - 895458,1014597,170644
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House 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. 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 available for owner occupancy now. 2nd floor unit lease ends 12/1. Do not miss this chance to live and have others cover your mortgage!

Highlights

Listed by Cory Tanzer , 312-500-5808 and Jamison Jordan , (773) 308-5324 Option Premier LLC , 312-500-5808. Midwest Real Estate Data mls logo

Property Type

Multi-Family

Year Built

1917

County

Cook

Area

CHI - Forest Glen

Neighborhood

Forest Glen

School District

299

Listing ID

12775522

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Interior Features

Bedrooms and Bathrooms
  • ▪ Bedrooms:4
  • ▪ Bathrooms:3
Appliances:CO Detectors,Ceiling Fan(s)
Basement:Finished,Exterior Entry,Concrete,Sleeping Area,Storage Space,Full
Water:Lake Michigan

Exterior Features

Lot Dimensions:31X126
Garage Capacity:3
Zoning:MULTI
Roof:Asphalt
Others:
  • ▪ Additional:Breezeway, Lighting
Sewer:Public Sewer
Parking Features:Garage Door Opener,Yes,Garage Owned,Detached,Additional Parking,Garage
Principal Interest
$3,058
Taxes
$754

Home Price

$569,999

Loan Details

30 yrs
7.08%

Down Payment

20%
$114,000
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$3,058.31

Principal

Taxes

Principal Taxes HOA Total
Monthly $3,058.31 $753.69 $0.00 $3,812.00
Yearly $36,699.76 $9,044.28 $0.00 $45,744.04
Total $1,100,992.78 $271,328.40 $0.00 $1,372,321.18
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Master Chief
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Market insight data is pulled from the same city as the listing being viewed (Chicago, IL).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Based on information submitted to the MRED as of the date listed below. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively 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. Data is deemed reliable but is not guaranteed by MTP or MRED. The use of the MRED Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time.

Based on information submitted to the MLS GRID as of the date listed below. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers' personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability. Some listings have been excluded from this website.

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Data last updated: 2026-10-27T04:57:04.000Z

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