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5037 W Winona St
Multi-Family
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$599,999

5037 W Winona St, Chicago

49% below median
3 bd·3 ba·0 sqft
Built 1917Forest Glen

5037 W Winona St, Chicago, IL

3 bd · 3 ba · 0 sqft Multi-Family listed at $599,999, built in 1917 in the Forest Glen neighborhood.

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.

Property details

Price
$599,999
Bedrooms
3
Bathrooms
3
Year built
1917
Type
Multi-Family
Days on market
51
Est. property tax
$12,480/yr · $1,040/mo · 2.08% IL avg
Last sold
$475,000 · Oct 2022

Estimated monthly payment

Down payment20% ($120,000)
Interest rate6.75%
Principal & Interest$3,113
Property Tax$550
Insurance$150
Total$3,813/mo

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Price history

$621K$495K$369K$390K on Feb 22 (Initial list)$390K on Apr 22 (Sold)$525K on Aug 22 (Initial list)$515K on Aug 22 (Price change)$500K on Aug 22 (Price change)$475K on Oct 22 (Sold)$600K on Mar 26 (Initial list)
$390K · Feb 22$600K · Mar 26
  1. Mar 6, 2026$599,999Initial list price
  2. Oct 21, 2022$475,000Sold
  3. Aug 29, 2022$499,900Price change
  4. Aug 15, 2022$515,000Price change
  5. Aug 1, 2022$525,000Initial list price
  6. Apr 6, 2022$390,000Sold
  7. Feb 22, 2022$390,000Initial list price

Location

This home is located in Chicago, IL. Browse more Chicago listings on the Chicago market page or explore the full Chicago market report.

About Chicago: Chicago is the most populous city in the U.S. state of Illinois and in the Midwestern United States. Located on the western shore of Lake Michigan, it is the third-most populous city in the United States, with a population of 2.74 million at the 2020 census. The Chicago metropolitan area has 9.41 million residents and is the third-largest metropolitan area in the country. Chicago is the seat of Cook County, the second-most populous county in the U.S. (source: Wikipedia)

Climate: Average year-round temperature is 51°F with 211 dry days per year and 39.9 inches of annual rainfall.

Location

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Home Intelligence

Neighborhood (zip 60630)

Median age is 40.6; 29% hold a bachelor's degree; 68% of homes are owner-occupied; median household income is $91,135.

Median income
$91,135
Median age
40.6
Owner-occupied
67.6%
Bachelor's degree
28.8%
Census median home value
$358,000

Source: US Census Bureau American Community Survey 5-year estimates.

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