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5037 W Winona Street

Chicago, IL 60630
  • $594,888
  • STATUS: Active
  • MLS #: 12688970
UPDATED: 95 min ago
$594,888
  • 4
    BEDS
  • N/A
    ACRES
  • 0
    BATHS
  • 0
    1/2 BATHS
Neighborhood:
Type:
Multi-Family
Built:
1917
County:

School Ratings & Info

School District:
299

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. 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.

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© 2026 Midwest Real Estate Data LLC. All rights reserved. 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. Information is deemed reliable but is not guaranteed accurate by MTP, MRED or Captivate Real Estate Group | eXp Realty LLC.

Based on information submitted to the MLS GRID as of 2026-07-17T15:27:47.833 UTC. 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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5037 W Winona Street Chicago, IL 60630

  • Price: $594,888
  • Status: Active
  • On Site: Days
  • Updated: 95 min ago
  • MLS #: 12688970
4
Beds
0
Baths
0
½ Baths
N/A
Acres
1917
Built
Neighborhood:
Forest Glen
County:
Cook
Area:
Chi - Forest Glen
School District:
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. 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.
Exterior Features

Exterior Features BreezewayLighting Foundation Details Concrete Perimeter Is Parking Included In Price Yes Lot Size Oversized Chicago Lot Multi Family Type 2 Flat Other Structures Garage(s) Parking Features Garage Door OpenerYesGarage OwnedDetachedAdditional ParkingGarage Parking Total 3 Roof Asphalt Waterfront YN No

Interior Features

Basement Details FinishedExterior EntryConcreteSleeping AreaStorage SpaceFull Bedrooms Below Grade 0 Bedrooms Total 4 Full Baths In Building 3 Half Baths In Building 0 Heating Natural GasForced Air Room Type KitchenEnclosed Porch Rooms Total 16

Property Features

Additional Parcels YN No Age 100+ Years Built Before1978 YN Yes Community Features ParkCurbsSidewalksStreet LightsStreet Paved Corporate Limits Chicago General Information Commuter BusCommuter TrainInterstate Access Mls Actual Status Active New Construction YN No Other Additional Income Garage/s Other Equipment CO DetectorsCeiling Fan(s) Ownership Fee Simple Rebuilt YN No Sewer Public Sewer Special Listing Conditions List Broker Must Accompany Tax Annual Amount 9044.28 Tax Year 2024 Total Numberof Unitsin Building 2 Township Jefferson Type Two to Four Units Water Source Lake Michigan Zoning MULTI

Listing courtesy of © 2026 Midwest Real Estate Data LLC as distributed by MLS GRID.
Listing provided courtesy of Option Premier LLC: 312-500-5808.



© 2026 Midwest Real Estate Data LLC. All rights reserved. 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. Information is deemed reliable but is not guaranteed accurate by MTP, MRED or Captivate Real Estate Group | eXp Realty LLC.

Based on information submitted to the MLS GRID as of 2026-07-17T15:27:47.833 UTC. 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Digital Millennium Copyright Act
 
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