7837 S Winchester Ave Chicago, IL 60620
Auburn Gresham NeighborhoodEstimated payment $1,661/month
About This Home
This well-maintained brick 2-flat in Auburn Gresham is exactly what smart buyers are looking for -- a chance to plant roots in an established neighborhood while building real wealth from day one. Live in one unit, rent the other, and let your tenant help cover your mortgage. Built in 1926 and thoughtfully updated of the years, this solid Chicago two-flat offers 2,278 square feet of living space across two units, four bedrooms, and two full baths. The big-ticket items have already been addressed -- new roof, gutters, and tuckpointing completed in 2025, along with updated flooring throughout. The full unfinished basement has good ceiling height, giving a future owner real options for additional living space, or storage. The boiler is 12 years old, functional and well maintained. Auburn Gresham is a neighborhood with deep roots and a strong sense of community, close to public transit, local dining, and everything the South Side has to offer. For the buyer who wants more than a house and is looking for a real asset, this one is worth a close look.
Property Details
Home Type
- Multi-Family
Est. Annual Taxes
- $1,484
Year Built
- Built in 1926
Home Design
- Flat Roof Shape
- Brick Exterior Construction
- Concrete Perimeter Foundation
Bedrooms and Bathrooms
- 4 Bedrooms
- 4 Potential Bedrooms
- 2 Bathrooms
Parking
- 2 Parking Spaces
- Parking Available
- Alley Access
- Off Alley Parking
Utilities
- Heating System Uses Steam
- Heating System Uses Natural Gas
- Lake Michigan Water
Additional Features
- Basement Fills Entire Space Under The House
- Lot Dimensions are 25x125
Community Details
- 2 Units
Listing and Financial Details
- Senior Tax Exemptions
- Homeowner Tax Exemptions
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $1,484 | $16,000 | $1,875 | $14,125 |
| 2024 | $1,484 | $16,000 | $1,875 | $14,125 |
| 2023 | $1,408 | $13,000 | $3,000 | $10,000 |
| 2022 | $1,408 | $13,000 | $3,000 | $10,000 |
| 2021 | $1,275 | $13,000 | $3,000 | $10,000 |
| 2020 | $1,317 | $13,501 | $3,000 | $10,501 |
| 2019 | $1,313 | $15,342 | $3,000 | $12,342 |
| 2018 | $1,293 | $15,342 | $3,000 | $12,342 |
| 2017 | $1,384 | $16,534 | $2,625 | $13,909 |
| 2016 | $1,790 | $16,534 | $2,625 | $13,909 |
| 2015 | $1,720 | $16,534 | $2,625 | $13,909 |
| 2014 | $2,582 | $13,919 | $2,437 | $11,482 |
| 2013 | $1,712 | $13,919 | $2,437 | $11,482 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 04/23/2026 04/23/26 | Pending | -- | -- | -- |
| 04/02/2026 04/02/26 | For Sale | $289,900 | -- | -- |
Source: Midwest Real Estate Data (MRED)
MLS Number: 12605788
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Listings courtesy of Midwest Real Estate Data (MRED) as distributed by MLS GRID.
Based on information submitted to the MLS GRID
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Ask me questions while you tour the home.