5037 W Winona Street, Chicago, IL

$569,999

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About 5037 W Winona Street

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!

Open House

Sun, Oct 18th, 2026 @ 11am - 1pm

Features of 5037 W Winona Street

MLS® # 12775522
Price $569,999
Bedrooms 4
Bathrooms 0.00
Year Built 1917
Type Residential Income
Sub-Type Two to Four Units
Status Active

Community Information

Address 5037 W Winona Street
Area CHI - Forest Glen
Subdivision Forest Glen
City Chicago
County Cook
State IL
Zip Code 60630

Amenities

Parking Spaces 3
Parking Garage Door Opener, Yes, Garage Owned, Detached, Additional Parking, Garage
# of Garages 2
Is Waterfront No
Has Pool No

Interior

Heating Natural Gas, Forced Air
Fireplace No
Has Basement Yes
Basement Finished, Exterior Entry, Concrete, Sleeping Area, Storage Space, Full

Exterior

Exterior Aluminum Siding
Exterior Features Breezeway, Lighting
Roof Asphalt
Foundation Concrete Perimeter

School Information

District 299

Additional Information

Days on Market 8
Zoning MULTI
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeOption Premier LLC

Listing Map

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Listing information last updated on October 12th, 2026 at 7:07pm CDT.