For Sale
New4 days ago
Multi family home for sale at 5445 S Winchester Ave, Chicago, IL 60621 | MLS# 12764451 | Listing updated on 2026-09-21
Photo 1 of Multi family home for sale at 5445 S Winchester Ave, Chicago, IL 60621 | MLS# 12764451 | Listing updated on 2026-09-21
Photo 2 of Multi family home for sale at 5445 S Winchester Ave, Chicago, IL 60621 | MLS# 12764451 | Listing updated on 2026-09-21
Photo 3 of Multi family home for sale at 5445 S Winchester Ave, Chicago, IL 60621 | MLS# 12764451 | Listing updated on 2026-09-21
Photo 4 of Multi family home for sale at 5445 S Winchester Ave, Chicago, IL 60621 | MLS# 12764451 | Listing updated on 2026-09-21
15+
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Street View

$399,500

Monthly Est:$1,988

  • Beds Icon4 Beds
  • Beds Icon
    2 Baths
  • Beds Icon--sqft

5445 S Winchester Ave, Chicago, IL 60621

$1,988/moEst:

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  • Multi Family

  • Built in 1918

  • $-- HOA

  • -- sqft lot

  • --/sqft

Description

Completely gut-rehabbed and fully renovated, this property is truly move-in ready with extensive new construction and upgrades throughout. The renovation includes all-new appliances, individual new HVAC systems for each unit, new electrical, new plumbing, new windows, a new roof, new siding, and a new fence. The property also features hard-wired security cameras for added peace of mind. From the major mechanical systems to the exterior improvements, virtually every aspect of the property has been newly updated. A rare opportunity to own a property with the benefits of a brand-new renovation without the uncertainty and expense of an older, partially updated building.

  • Houzeo last checked: 7 minutes ago
  • Listing updated: September 21, 2026 at 4:58 pm
  • Listing Provided by: Vanessa Carlson | Illinois Discount Realty (800) 403-8716
  • Source: MRED MLS-IL | MLS#: 12764451 MRED MLS-IL

Part of

Building
5445 S Winchester Ave
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Property Details

  • Status

    Active

  • Type

    Multi Family

  • No. of Stories

    -

  • County

    Cook County

  • City

    Chicago

  • Neighborhood

    New City

  • Year Built

    1918

  • HOA Fees

    -

  • Finished Area

    - sqft

  • Lot Size

    -- sqft lot

  • Basement Area

    - sqft

  • MLS Name

    MRED MLS

  • MLS Number

    12764451

  • MLS Status

    New

  • Days on Market

    4

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Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 2

Interior

  • Heating

    Natural Gas, Electric

  • Sewer

    Public Sewer

Construction

  • Year Built

    Year Built: 1918

  • Home type

    Multi Family

  • Roof

    Asphalt

  • Foundation Details

    Concrete Perimeter

  • Construction Materials

    Vinyl Siding

Utilities & Energy

  • Water Source

    Lake Michigan

  • Basement

    Other, Full, Walk Out Access

  • Parking Features

    Driveway, Enclosed, Yes

Other Features

  • Community Features

    Sidewalks, Street Lights, Street Paved

  • Lot Features

    Corner Lot

Price History

DateEventPrice

09/20/2026

Source: mls_logoMRED MLS-IL #MRD12764451

Listed for Sale

$399,500 +66.46%

$0/sqft

11/06/2013

Source: mls_logoMRED MLS-IL #MRD08460713

Listing Removed

$240,000

$0/sqft

New City Ranks #144 in Chicago, IL

Homes for sale
70

Homes

Rental prices
$988

Rental Prices

Median Home Price
$255K

Median Home Price

New City, Chicago, IL neighborhood guide

This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC through Sep 24, 2026, 06:01PM. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.

Based on information submitted to the MLS GRID as of Sep 24, 2026, 06:01PM. All data is obtained from various sources and has not been, and will not be, 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. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. Some IDX listings have been excluded from this website. Information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID, MRED or Houzeo. The use of the MLS GRID Data may be subject to an end user license agreement. Properties displayed may be listed or sold by various participants in the MLS,

Listings courtesy of MRED as distributed by MLS GRID. ©2026 Midwest Real Estate Data LLC. All Rights Reserved

Advertising Broker: Jorge Romero | Realty One Group Inc.

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