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5527 S Winchester Avenue

Chicago, IL 60636

5 beds
2 baths
– sqft
3,485 sqft lot
1907 build
– on site

Amazing opportunity in Chicago's New City neighborhood ready for the final touch to bring this building to its full potential. The building features 2 apartments and a full unfinished basement with 3 bed/1 bath unit and a 2 bed/1 bath unit. Both units have brand-new plumbing, electrical panels, and wiring, along with new 2x4 framing throughout. The second-floor unit has all new windows, HVAC and ductwork, insulation, recessed lighting setup, a new in-unit breaker box, and a flat new roof. The porch on the second floor has also been enclosed with new windows. The first-floor unit includes a rebuilt front porch with new windows and siding. Additional improvements include a completely redone back porch and partial brick tuckpointing. Plenty of materials are on-site for continued work, see additional info. The detached garage needs replacement, and the property is fully fenced. Great investment potential for rental income or live-in owner. Sold as-is.

Listing courtesy of MRED / Re/Max In The Village as distributed by MLS GRID

Last checked: Checking… • Last updated Jun 25, 2025 •

MLS# 12388546 —

The Building

Year Built:

1907
Rebuilt:

No
New Construction:

false
Construction Materials:

Brick
Roof:

Asphalt
Basement:

Cellar, Partial

Interior

Rooms Total:

11

Location

Directions:

55th St West to Winchester Ave
Location:

90706

The Property

Parcel Number:

20182010130000
Property Type:

Residential Income
Location:

A
Lot Features:

Landscaped
Lot Size Dimensions:

30X125
Lot Size Acres:

0.08
Zoning:

MULTI
Waterfront:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2023
Tax Annual Amount:

2109.9

Beds

Bedrooms Total:

5
Bedrooms Possible:

5

Baths

Baths:

2
Full Baths:

2

The Listing

Special Listing Conditions:

None

Heating & Cooling

Heating:

Natural Gas

Utilities

Sewer:

Public Sewer
Water Source:

Public

Schools

Elementary School District:

299
Middle Or Junior School District:

299
High School District:

299

The Community

Community Features:

Curbs, Sidewalks, Street Lights, Street Paved

Parking

Parking Total:

2
Parking Features:

Garage Door Opener, On Site, Garage Owned, Detached, Garage
Garage Spaces:

2

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Transit Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Sale history

Date	Event	Source	Price	% Change
6/25/25 Jun 25, 2025	Listed / Active	MRED	$250,000	443.5% (49.0% / YR)
6/10/16 Jun 10, 2016		MRED	$46,000

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This multifamily located in Southwest Side, Chicago, IL 60636 is currently for sale for $250,000. 5527 S Winchester Avenue is a – square foot multifamily with 5 beds and 2 baths that has been on Estately for 0 days. 5527 S Winchester Avenue is in the Southwest Side neighborhood of Chicago and has a WalkScore® of 64, making it somewhat walkable. This multifamily is in the attendance area of Charles R Henderson Elementary School and Englewood Stem High School.

Listing courtesy of MRED, Re/Max In The Village, and Erika Villegas as distributed by MLS GRID.

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Signal Real Estate are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
© 2025 Midwest Real Estate Data LLC
Information deemed reliable but not guaranteed by MLS GRID. Use of MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time.

Based on information submitted to MLS GRID as of Jun 25, 2025, 07:15 pm. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.