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$399,900
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Property Description
Two-Flat Opportunity with Owner-Occupant Potential! Looking for a two-flat with starter home potential? Look no further than 5239 S Troy St, Chicago, IL 60632! This beautifully maintained and updated property offers a great opportunity for both homeowners and investors - all while benefiting from low property taxes. This well-cared-for building features two units with a total of five bedrooms: Second Floor Unit * 3 Bedrooms | 1 Bathroom * Duplexed into the attic for additional living space * Washer & dryer hookups available * Freshly painted and move-in ready for the next owner First Floor Unit * 2 Bedrooms | 1 Bathroom * Cozy and comfortable layout Set back from the street, the property features a large fenced-in front yard, offering great outdoor space for relaxing, entertaining, or enjoying a bit of privacy. Major updates have already been completed, including: Whether you're a first-time buyer looking to live in one unit and rent the other or an investor seeking another strong addition to your portfolio, this property offers both flexibility and value. Schedule your showing today!
Full Property Details
Full Property Details for 5239 S Troy St
General
- Price: $399,900
- Taxes: $3,834 (2024)
- Status: Active
- Type: Multi-Family
- Source: MRED
- MLS ID: 12584673
- Updated: 3/11/2026
- Added to Site: 17 day(s) ago
Interior
- Basement: None
Rooms
Bathrooms
- Total Bathrooms: 2
- Upper - Full Baths: 2
Bedrooms
- Total Bedrooms: 5
Location
- Area: CHI - Gage Park
- County: Cook
- Township: Lake
- Driving Directions: HEAD SOUTH ON KEDZIE, LEFT ON 53RD ST, LEFT ON ALBANY, LEFT ON 52ND, LEFT ON TROY TO HOME
School Information
- School District: 299
- Elem School District: 299
- Midd School District: 299
- High School District: 299
Heating & Cooling
- Heating Type: Natural Gas, Forced Air
Utilities
- Sewer: Public Sewer
- Water: Lake Michigan, Public
Structural Information
- Construction: Vinyl Siding
- Exterior Const.: Vinyl Siding
- Basement Desc.: None
- Roof: Asphalt
- Year Built: 1918
- Built Before 1978: Yes
Unit Information
- Units in Building: 2
Additional Structures
- Other Structures: Shed(s)
Lot Features
- Lot Size Range: Less than .25 Acre
- Lot Dimensions: 3750 SQ FT
Financial Considerations
- Assessment Year: 1918
- Tax Amount: $3,834
- Tax Year: 2024
- Pays Sewer: Public Sewer
Disclosures and Reports
- Ownership: Fee Simple
- Property ID: 19123090140000
Listed by WE Realty
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Schools
Schools serving 5239 S Troy St
School District:Chicago Public School District 299
| Name | Grades | Distance |
|---|---|---|
Sawyer Elementary School, Chicago, IL 5248 South Sawyer Avenue, Chicago, IL 60632 | K-8 | 0.2 mi |
Curie Metropolitan High School 4959 South Archer Avenue, Chicago, IL 60632 | 9-12 | 1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5239 S Troy St
Date
Details
Price
Change
Source
3/05/2026
Listed
$399,900
81.77%
MLS
1/30/2023
Sold
$220,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 5239 S Troy St
Year
Property Taxes
Change
Tax Assessment
Change
2023
$2,054
4%
$12,999
—
2022
$1,981
2%
$12,999
—
2021
$1,944
6%
$12,999
15%
2020
$1,837
-6%
$11,297
-14%
2019
$1,963
2%
$13,137
—
2018
$1,929
-2%
$13,137
5%
2017
$1,976
-2%
$12,493
—
2016
$2,015
11%
$12,493
—
2015
$1,822
—
$12,493
1%
2014
$1,824
3%
$12,321
—
2013
$1,777
—
$12,321
—
2012
$1,778
—
$12,321
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5239 S Troy St
5239 S Troy Street, Chicago, IL 60632 (MLS# 12584673) is a Multi-Family property with 2 units containing 5 bedrooms and 0 full bathrooms. 5239 S Troy Street is currently listed for $399,900 and was received on March 05, 2026. Want to learn more about 5239 S Troy Street? Do you have questions about finding other Multi-Family real estate for sale in Gage Park? You can browse all Gage Park real estate or contact a Coldwell Banker agent to request more information.

