Listing provided courtesy of Option Premier LLCMREDas Distributed by MLSGrid- MLS# 12688970MLS Provider

5037 W Winona StreetChicago, IL 60630

Multi-Family · 3 Beds
$594,888 New

5037 W Winona Street Overview

Time on Site:
4 days
Visits:
0

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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5037 W Winona Street Facts & Features

  • Type Multi-Family

Details

General

School Information

  • School District: 299

Building Information

  • New Construction: No
  • Year Built: 1917

Location/Region

  • County Or Parish: Cook
  • MLS Area Major: CHI - Forest Glen
  • Subdivision Name: Forest Glen
  • Township: Jefferson

Community/Development

  • Community Features: Park, Curbs, Sidewalks, Street Lights, Street Paved

Tax Information

  • Tax Annual Amount: $6,756.00
  • Tax Year: 2023

General Information

  • Ownership: Fee Simple
  • Parcel Number: 13094060080000
  • Property Type: Residential Income
  • Special Listing Conditions: List Broker Must Accompany
  • Zoning: MULTI

Interior

Parking Information

  • Half Baths Building: 0
  • Garage Spaces: 2

Beds/Baths

  • Bathrooms Total: 3
  • Bedrooms Total: 4
  • Bedrooms Possible: 4
  • Full Baths Building: 3

General Information

  • Basement: Finished, Exterior Entry, Concrete, Sleeping Area, Storage Space, Full
  • Foundation Details: Concrete Perimeter
  • Heating: Natural Gas, Forced Air
  • Other Equipment: CO Detectors, Ceiling Fan(s)
  • Rooms Total: 16
  • Window Features: Screens

Exterior

Parking Information

  • Parking Features: Garage Door Opener, Yes, Garage Owned, Detached, Additional Parking, Garage
  • Parking Total: 3

Lot Information

  • Additional Parcels: No
  • Lot Size Dimensions: 31X126
  • Water Source: Lake Michigan

Waterfront/View

  • Waterfront: No

Building Exterior/Construction

  • Construction Materials: Aluminum Siding
  • Roof: Asphalt

General Information

  • Exterior Features: Breezeway, Lighting
  • Other Structures: Garage(s)
  • Sewer: Public Sewer

Unit Information

Unit 1 Details

  • Unit Type: Unit 1
  • Actual Rent: 1850
  • Beds Total: 2
  • Baths Total: 1

Unit 2 Details

  • Unit Type: Unit 2
  • Actual Rent: 1700
  • Beds Total: 1
  • Baths Total: 1

5037 W Winona Street Neighborhood

Community

60630 (Chicago) Demographics

40
Median Age
11,662
Population Density (per sq. mile)
49%
College Educated
$78,703
Estimated Median Income
13,868
Estimated Total Home Owners
7,000
Estimated Total Renters
66% / 34%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

5037 W Winona Street Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

5037 W Winona Street Market Data

Based on the last 30 days in this zip code

$524,541
Average List Price
$355
Average Price per Square Foot
37
Properties Sold
32
Average Days on Market
83
Properties for Sale
Calculations provided by Reliance Network

5037 W Winona Street History

Date Event Value Agent
6/25/2026Source: MRED Added to Database
June 25, 2026
10/21/2022Source: MRED Status Change
Closed
9/13/2022Source: MRED Status Change
Contingent
9/3/2022Source: MRED Status Change
Active
8/29/2022Source: MRED Price Reduction
$499,900 -2.9%
8/29/2022Source: MRED Status Change
Price Change
8/20/2022Source: MRED Status Change
Active
8/15/2022Source: MRED Price Reduction
$515,000 -1.9%
8/15/2022Source: MRED Status Change
Price Change
8/6/2022Source: MRED Status Change
Active
8/1/2022Source: MRED Added to Database
August 01, 2022
6/20/2022Source: MRED Added to Database
February 22, 2022
4/7/2022Source: MRED Status Change
Closed