Active

$569,999

5037 Winona Street, Chicago, IL 60630
4 Beds3 Baths7 days
5037 Winona Street·Chicago, IL 60630
4Bedrooms
3Bathrooms
1917Year Built
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. 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 availabe for owner occupancy now. Do not miss this chance to live and have others cover your mortage!

MLS# 12775522Listed October 2, 2026Residential IncomeSubdivision: Forest Glen
Property Details

Beds & Baths

Total Bedrooms4
Total Bathrooms3
Total Rooms16

Size & Structure

Garage Spaces2
Year Built1917
Lot Size31X126

Location

CountyCook
TownshipJefferson
SubdivisionForest Glen
Zip Code60630

Financial

List Price$569,999
Annual Taxes (2024)$9,044
Monthly Tax Est.$754
Parcel #13094060080000
Interior Features

Heating

Natural GasForced Air

Basement

FinishedExterior EntryConcreteSleeping AreaStorage SpaceFull
Exterior & Lot

Construction

Aluminum Siding

Roof

Asphalt

Foundation

Concrete Perimeter

Exterior Features

BreezewayLighting

Patio & Porch

PatioPorch
Utilities & Parking

Sewer

Public Sewer

Water Source

Lake Michigan

Parking

Garage Door OpenerYesGarage OwnedDetachedAdditional ParkingGarage
HOA & Community

Community Features

ParkCurbsSidewalksStreet LightsStreet Paved
Tax & Financial
Annual Taxes
$9,044
Tax Year 2024
Monthly Tax Est.
$754
per month
Property Location

5037 Winona Street, Chicago, IL 60630 — Cook County

$569,999
5037 Winona Street
4 bd3 ba
VL
Vittoria Logli
Top Glenview Agent

IL License 475.178467 · (847) 810-8438

Quick Facts
7 days on market
2-car garage
31X126
$9,044/yr taxes
$3,749
estimated monthly payment
Principal & Interest
$2,996/mo
Property Tax
$754/mo
$569,999
20% — $114,000
3%50%
6.875%
3%12%
Loan Amount
$455,999
Down Payment
$114,000

* Estimated payment only. Actual rates, taxes, and insurance may vary. Contact a lender for a personalized quote.

Listed by
Option Premier LLC
Agent: Cory Tanzer
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Listing Courtesy: MRED as distributed by MLS GRID | @properties Christie's International Real Estate

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