Active

5037 Winona Street

Chicago, IL 60630
$599,999
3beds
3baths
sqft
Ask Dwello about this home
Anything from "is it priced right?" to "what's the catch?"

About this home

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.
MLS Description — as provided by the listing brokerage.

The facts

Property typeResidential Income
Year built1917
Garage spaces2
Lot size
SubdivisionForest Glen
Annual tax$6,756
CountyCook
MLS #MRD12584323
Days on market23

Features

Heating
Natural GasForced Air
Parking
Garage Door OpenerYesGarage OwnedDetachedGarage
Construction
Aluminum Siding
Sewer
Public Sewer
Listed by
Option Premier LLC
Cory Tanzer

Listing courtesy of mred MLS as distributed by MLS GRID.

Based on information submitted to the MLS GRID as of 3/27/2026, 11:47:05 PM. All data should be independently verified.

You + your agent

What do you think?

React below so your dwello agent knows how you feel. Leave a note to start a conversation about this home.

Loading…