Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$384,500 -$15,000 (-3.75%) Price Reduced

  • For Sale
  • Active
  • Multi-Family
  • 4 Total Beds
  • Updated 19 hours ago
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 5445 S Winchester Ave

General

  • Price: $384,500
  • Taxes: $1,567 (2025)
  • Status: Active
  • Type: Multi-Family
  • Source: MRED
  • MLS ID: 12764451
  • Updated: 10/1/2026
  • Added to Site: 12 day(s) ago

Rental Information

  • Complex Features: Sidewalks, Street Lights, Street Paved

Interior

  • Basement: Other, Full

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Upper - Full Baths: 2

Bedrooms

  • Total Bedrooms: 4

Additional Information

  • Equipment: Security System, Carbon Monoxide Detectors, Ceiling Fan(s), Multiple Water Heaters
  • Other Features: Commuter Bus

Parking

  • Total Spaces: 2
  • Parking Features: Driveway, Enclosed, Yes

Location

  • Area: CHI - New City
  • County: Cook
  • Township: Lake
  • Driving Directions: ake I-90/I-94 to 55th St. Exit. Head west on 55th St., then south on Winchester Ave. Property is located on the west side of the street.

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299

Heating & Cooling

  • Heating Type: Natural Gas, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Lake Michigan

Structural Information

  • Construction: Vinyl Siding
  • Exterior Const.: Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Other, Full, Walk-Out Access
  • Foundation: Concrete Perimeter
  • Roof: Asphalt
  • Year Built: 1918
  • Built Before 1978: Yes
  • Remodeled/Updated: 2026

Unit Information

  • Units in Building: 2

Lot Features

  • Lot Size Range: Standard Chicago Lot
  • Lot Dimensions: 25 x 125
  • Lot Features: Corner Lot
  • Zoning: MULTI

Financial Considerations

  • Assessment Year: 1918
  • Tax Amount: $1,567
  • Tax Year: 2025
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 20074250180000

Listed by Elite Value Real Estate

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 5445 S Winchester Ave —

  • Elite Value Real Estate

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Get a Great Insurance Rate

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 5445 S Winchester Ave

School District:Chicago Public School District 299
NameGradesDistance
Fulton Elementary School, Chicago, IL
5300 South Hermitage Avenue, Chicago, IL 60609
PK-80.3 mi
Tilden Career Communty Academy High School
4747 South Union Avenue, Chicago, IL 60609
9-121.8 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 5445 S Winchester Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/25/2026
Price Reduced
$384,500
-3.75%
MLS
9/20/2026
Listed
$399,500
1231.67%
MLS
11/10/2009
Sold
$30,000
—
Public Record
Get Price Alerts and Save Property
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 for 5445 S Winchester Ave

Year
Property Taxes
Change
Tax Assessment
Change
2023
-100%
-100%
2022
$931
3%
$4,499
—
2021
$905
-42%
$4,499
-36%
2020
$1,566
-4%
$6,986
-13%
2019
$1,624
2%
$8,030
—
2018
$1,597
-41%
$8,030
-36%
2017
$2,715
7%
$12,528
—
2016
$2,526
9%
$12,528
—
2015
$2,312
-2%
$12,528
-1%
2014
$2,362
2%
$12,633
—
2013
$2,316
1%
$12,633
—
2012
$2,285
—
$12,633
—
View All
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 for 5445 S Winchester Ave

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Elite Value Real Estate

Similar Properties near 5445 S Winchester Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

6225 S Seeley Ave, Chicago, IL 60636 - Photo 1 Just Listed
$385,000

6225 S Seeley Ave  Chicago, IL 60636

  • Multi-Family
  • Active
  • Updated 3 days ago
  • 4
    Total Beds
4505 S Fairfield Ave, Chicago, IL 60632 - Photo 1
$390,000

4505 S Fairfield Ave  Chicago, IL 60632

  • Multi-Family
  • Active
  • 4
    Total Beds
7409 S Stewart Ave, Chicago, IL 60621 - Photo 1 Price Reduced
-$10,000 (-2.53%)
$384,999

7409 S Stewart Ave  Chicago, IL 60621

  • Multi-Family
  • Active
  • Updated 5 hours ago
  • 4
    Total Beds
3824 S Sacramento Ave, Chicago, IL 60632 - Photo 1
$380,000

3824 S Sacramento Ave  Chicago, IL 60632

  • Multi-Family
  • Active
  • Updated 8 days ago
  • 4
    Total Beds

Just Listed near 5445 S Winchester Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5122 W 30th Pl, Cicero, IL 60804 - Photo 1 Just Listed
$585,000

5122 W 30th Pl  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 3 days ago
  • 5
    Total Beds
1438 S 51st Ave, Cicero, IL 60804 - Photo 1 Just Listed
$330,000

1438 S 51st Ave  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 19 hours ago
  • 6
    Total Beds
2617 S 60th Ct, Cicero, IL 60804 - Photo 1 Just Listed
$389,900

2617 S 60th Ct  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 1 day ago
  • 6
    Total Beds
5431 W 30th Pl, Cicero, IL 60804 - Photo 1 Just Listed
$575,000
Open House

5431 W 30th Pl  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 17 hours ago
  • 6
    Total Beds

Price Reduced near 5445 S Winchester Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5326 W 31st St, Cicero, IL 60804 - Photo 1 Price Reduced
-$29,000 (-4.15%)
$670,000
Open House

5326 W 31st St  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 2 days ago
  • 6
    Total Beds
5431 W 25th St, Cicero, IL 60804 - Photo 1 Price Reduced
-$15,000 (-3.33%)
$434,900

5431 W 25th St  Cicero, IL 60804

  • Business
  • Active
  • Updated 5 hours ago
  • 1,750
    Sq. Ft.
1324 S 48th Ct, Cicero, IL 60804 - Photo 1 Price Reduced
-$14,900 (-3.92%)
$365,000

1324 S 48th Ct  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 19 hours ago
  • 6
    Total Beds
3611 S 55th Ct, Cicero, IL 60804 - Photo 1 Price Reduced
-$5,000 (-1.01%)
$489,000

3611 S 55th Ct  Cicero, IL 60804

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,181
    Sq. Ft.

Recent Sales near 5445 S Winchester Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5540 S Honore St, Chicago, IL 60636 - Photo 1 Sold
$400,000

5540 S Honore St  Chicago, IL 60636

  • Multi-Family
  • Closed
  • 9
    Total Beds
5515 S Oakley Ave, Chicago, IL 60636 - Photo 1 Sold
$336,000

5515 S Oakley Ave  Chicago, IL 60636

  • Single Family
  • Closed
  • 5
    Beds
  • 2
    Total Baths
  • 969
    Sq. Ft.
2101 W 51st St, Chicago, IL 60609 - Photo 1 Sold
$375,000

2101 W 51st St  Chicago, IL 60609

  • Multi-Family
  • Closed
  • 7
    Total Beds
5628 S Justine St, Chicago, IL 60636 - Photo 1 Sold
$360,000

5628 S Justine St  Chicago, IL 60636

  • Multi-Family
  • Closed
  • 10
    Total Beds

5445 S Winchester Avenue, Chicago, IL 60621 (MLS# 12764451) is a Multi-Family property with 2 units containing 4 bedrooms and 0 full bathrooms. 5445 S Winchester Avenue is currently listed for $384,500 and was received on September 20, 2026. Want to learn more about 5445 S Winchester Avenue? Do you have questions about finding other Multi-Family real estate for sale in New City? You can browse all New City real estate or contact a Coldwell Banker agent to request more information.

Tour this property