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. 1st floor unit availabe for owner occupancy now. Do not miss this chance to live and have others pay your mortage!
Active
$579,999
5037 W Winona St, Chicago, IL 60630
3beds
--sqft
Multi Family
Built in 1917
-- sqft lot
$571,000 Zestimate®
$--/sqft
$-- HOA
What's special
Finished basementGenerous bedroomFully fenced in yardPrivacy fenceWalk-in pantryEat-in breakfast areaSpacious kitchen
- 7 days
- 222
- 10
Zillow last checked:
Listing updated:
Listed by:
Cory Tanzer 312-500-5808,
Option Premier LLC,
Jamison Jordan 773-308-5324,
Option Premier LLC
Source: MRED as distributed by MLS GRID,MLS#: 12744009
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 3
Rooms
- Room types: Kitchen, Enclosed Porch
Heating
- Natural Gas, Forced Air
Features
- Windows: Screens
- Basement: Finished,Exterior Entry,Concrete,Sleeping Area,Storage Space,Full
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Garage Door Opener, Yes, Garage Owned, Detached, Additional Parking, Garage
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Patio, Porch
- Exterior features: Breezeway, Lighting
- Fencing: Fenced,Wood
Lot
- Size: 3,906 Square Feet
- Dimensions: 31X126
Details
- Additional structures: Garage(s)
- Parcel number: 13094060080000
- Zoning: MULTI
- Special conditions: List Broker Must Accompany
- Other equipment: Ceiling Fan(s)
Construction
Type & style
- Home type: MultiFamily
- Property subtype: Multi Family
Materials
- Aluminum Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1917
Utilities & green energy
- Sewer: Public Sewer
- Water: Lake Michigan
Community & HOA
Community
- Features: Park, Curbs, Sidewalks, Street Lights, Street Paved
- Security: Carbon Monoxide Detector(s)
- Subdivision: Forest Glen
Location
- Region: Chicago
Financial & listing details
- Tax assessed value: $450,000
- Annual tax amount: $9,044
- Date on market: 8/27/2026
- Ownership: Fee Simple
Estimated market value
$571,000
$542,000 - $600,000
$2,418/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/27/2026 | Listed for sale | $579,999 |
Source: MRED as distributed by MLS GRID #12744009 Report a problem | ||
| 8/27/2026 | Listing removed | $579,999 |
Source: MRED as distributed by MLS GRID #12714777 Report a problem | ||
| 8/11/2026 | Contingent | $579,999 |
Source: | ||
| 7/24/2026 | Listed for sale | $579,999-2.5% |
Source: | ||
| 7/24/2026 | Listing removed | $594,888 |
Source: MRED as distributed by MLS GRID #12688970 Report a problem | ||
| 6/26/2026 | Listed for sale | $594,8880% |
Source: | ||
| 6/26/2026 | Listing removed | $594,999 |
Source: MRED as distributed by MLS GRID #12649714 Report a problem | ||
| 5/15/2026 | Listed for sale | $594,999-0.8% |
Source: MRED as distributed by MLS GRID #12649714 Report a problem | ||
| 5/15/2026 | Listing removed | $599,999 |
Source: | ||
| 3/6/2026 | Listed for sale | $599,999+26.3% |
Source: | ||
| 10/21/2022 | Sold | $475,000-5% |
Source: | ||
| 9/13/2022 | Contingent | $499,900 |
Source: | ||
| 8/29/2022 | Price change | $499,900-2.9% |
Source: | ||
| 8/15/2022 | Price change | $515,000-1.9% |
Source: | ||
| 8/1/2022 | Listed for sale | $525,000+34.6% |
Source: | ||
| 4/6/2022 | Sold | $390,000+161.7% |
Source: | ||
| 11/4/1994 | Sold | $149,000 |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $9,044 +33.9% | $45,000 +40.6% |
| 2023 | $6,756 +27% | $32,000 |
| 2022 | $5,319 +32.4% | $32,000 |
| 2021 | $4,017 +0.3% | $32,000 +32.3% |
| 2020 | $4,006 -3.3% | $24,179 -12% |
| 2019 | $4,145 +1.8% | $27,477 |
| 2018 | $4,073 -14.4% | $27,477 -15.1% |
| 2017 | $4,755 -6.9% | $32,354 |
| 2016 | $5,105 +4% | $32,354 |
| 2015 | $4,907 +14.1% | $32,354 +17.4% |
| 2014 | $4,299 -14.3% | $27,555 |
| 2013 | $5,015 +9.7% | $27,555 -7.3% |
| 2012 | $4,571 -3.8% | $29,730 -14.3% |
| 2011 | $4,753 -15.9% | $34,693 |
| 2010 | $5,650 +81.1% | $34,693 -3.4% |
| 2009 | $3,120 +3.2% | $35,922 +0% |
| 2008 | $3,022 -26.9% | $35,915 -9% |
| 2007 | $4,136 +23% | $39,474 |
| 2006 | $3,363 +9.2% | $39,474 +49.8% |
| 2005 | $3,079 -3.7% | $26,352 |
| 2004 | $3,198 +4.4% | $26,352 |
| 2003 | $3,062 -5.4% | $26,352 +32.9% |
| 2002 | $3,237 +4.8% | $19,823 |
| 2001 | $3,088 +15.5% | $19,823 |
| 2000 | $2,674 | $19,823 +24.7% |
| 1999 | $2,674 | $15,894 |
Find assessor info on the county website
Monthly payment
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