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$949,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 8 Total Beds
  • 2 Car Garage
  • Updated 1 day ago
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Turnkey, classic Andersonville greystone offering three legal units on a wide lot. All units feature open-concept kitchens and granite baths. Bright and sunny throughout with high ceilings, hardwood floors, and gas-forced air heat. Extensive capital improvements include 2022 renovation of garden unit (new flooring, appliances, paint, etc.) New windows in 1st and 2nd floor units, refreshed common areas and 2nd floor main living spaces. The property also offers a landscaped, private fenced yard. Located on a quiet, tree-lined street just steps from Andersonville's dining and shopping district, Foster Beach, the Red Line, and Metra. Great opportunity for an investor or live-in owner in a prime location.

Full Property Details for 1427 W Winona St

General

  • Price: $949,000
  • Taxes: $16,273 (2024)
  • Status: Active
  • Type: Multi-Family
  • Source: MRED
  • MLS ID: 12602618
  • Updated: 4/13/2026
  • Added to Site: 2 day(s) ago

Interior

  • Basement: Finished, P

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Upper - Full Baths: 3

Bedrooms

  • Total Bedrooms: 8

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Yes, Garage Owned, Detached, Garage

Location

  • Area: CHI - Uptown
  • County: Cook
  • Township: Lake View
  • Driving Directions: Clark St to Winona (5150N) east to 1427 W Winona St

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

Structural Information

  • Construction: Brick, Stone
  • Exterior Const.: Brick, Stone
  • Basement: Yes
  • Basement Desc.: Finished, Partial
  • Year Built: 1905
  • Built Before 1978: Yes

Unit Information

  • Units in Building: 3

Lot Features

  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 30 x 129
  • Zoning: MULTI

Financial Considerations

  • Parking Included: Yes
  • Assessment Year: 1905
  • Tax Amount: $16,273.74
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 14083040190000

Listed by @properties Christie's International Real Estate

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— 1427 W Winona St —

  • @properties Christie's International Real Estate

  • @properties Christie's International Real Estate

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NMLS#: 1598647

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

Schools serving 1427 W Winona St

School District:Chicago Public School District 299
NameGradesDistance
Mccutcheon Elementary School
4865 North Sheridan Road, Chicago, IL 60640
PK-80.6 mi
Senn High School
5900 North Glenwood Avenue, Chicago, IL 60660
9-121 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 1427 W Winona St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/12/2026
Listed
$949,000
21.05%
MLS
12/17/2019
Sold
$784,000
—
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 1427 W Winona St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$12,811
3%
$60,718
—
2022
$12,489
-6%
$60,718
-8%
2021
$13,272
7%
$66,000
18%
2020
$12,427
-1%
$55,783
-11%
2019
$12,593
2%
$62,678
—
2018
$12,381
6%
$62,678
15%
2017
$11,703
13%
$54,365
—
2016
$10,389
10%
$54,365
—
2015
$9,481
10%
$54,365
11%
2014
$8,624
2%
$49,049
—
2013
$8,443
6%
$49,049
—
2012
$7,949
—
$49,049
—
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.

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1427 W Winona Street, Chicago, IL 60640 (MLS# 12602618) is a Multi-Family property with 3 units containing 8 bedrooms and 0 full bathrooms. 1427 W Winona Street is currently listed for $949,000 and was received on April 12, 2026. Want to learn more about 1427 W Winona Street? Do you have questions about finding other Multi-Family real estate for sale in Uptown? You can browse all Uptown real estate or contact a Coldwell Banker agent to request more information.

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