Properties

Features
: Gas , Forced Air
: Full , Exterior Entry , Storage Space , Finished , Sleeping Area , Concrete
: Wood , Fenced
: Patio , Porch
: Additional Parking , Garage Door Opener , Detached , Garage , Garage Owned , Yes
: Breezeway , Lighting
: Public Sewer
: Screens
Address Map
US
IL
Cook
Chicago
Forest Glen
60630
Winona
5037
Street
W88° 14' 44.5''
N41° 58' 26.9''
Foster to LeClaire (South) to Winona (East) to property.
CHI - Forest Glen
W
MULTI
Neighborhood
299
299
299
Additional Information
: Park , Curbs , Street Paved , Sidewalks , Street Lights
: Aluminum Siding
: Concrete Perimeter
2
31X126
https://www.zillow.com/view-imx/7a88709f-4b5d-4cdd-939b-8271ec5693d8?wl=true&setAttribution=mls&initialViewType=pano
: Lake Michigan
Option Premier LLC
Cory Tanzer
Financial
9044.28
Listing Information
Jamison Jordan
1014597
88528
Option Premier LLC
895458
88528
Contingent
2026-10-23T13:46:03Z
MRED
: List Broker Must Accompany
2026-10-23T13:45:04Z
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. 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!

Residential Income For Sale

5037 W Winona Street, Chicago, Illinois 60630

  • Bedrooms : 4
  • Bathrooms : 3
$569,999
Listing ID#12775522
QR Code
Basic Details
Property Type : Residential Income
Listing Type : For Sale
Listing ID : 12775522
Price : $569,999
Bedrooms : 4
Rooms : 16
Bathrooms : 3
Year Built : 1917
Listing Status : Active Under Contract
Roof : Asphalt
Contact Agent
Open Dates
  • 1. 2026-10-24 (Start time: 2026-10-24T16:00:00Z - End time: 2026-10-24T17:30:00Z)