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$1,350,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 6 Total Beds
  • 2 Car Garage
  • Updated 5 days ago
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ANDERSONVILLE brick 3-flat - turnkey investment property! All three units are classic 2-bedroom, 1-bath layouts featuring spacious kitchens, separate dining rooms, enclosed 3-season sunrooms off the kitchens, and hardwood floors throughout. Newer kitchens and baths. Beautiful backyard with patio and brick 2-car garage. Well-maintained property with numerous updates. Recent improvements include tuckpointing and a new garage roof in 2023, plus a new boiler in 2024. Unfinished basement offers potential for a 1st-floor duplex or new garden apartment through Chicago's ADU program. Don't miss the opportunity to invest in one of Chicago's hottest neighborhoods.

Full Property Details for 1461 W Winona St

General

  • Price: $1,350,000
  • Taxes: $18,260 (2025)
  • Status: Active
  • Type: Multi-Family
  • Source: MRED
  • MLS ID: 12774861
  • Updated: 10/4/2026
  • Added to Site: 6 day(s) ago

Interior

  • Basement: Unfinished

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 6

Parking

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

Location

  • Area: CHI - Uptown
  • County: Cook
  • Township: Lake View
  • Driving Directions: Glenwood to Winona. West on Winona to 1461.

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299
  • Elementary School: Mccutcheon Elementary School
  • High School: Senn High School
  • Private School: Senn High School

Heating & Cooling

  • Heating Type: Steam, Radiator(s)

Utilities

  • Sewer: Public Sewer
  • Water: Lake Michigan

Structural Information

  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • Basement Desc.: Unfinished, Full
  • Year Built: 1914
  • Built Before 1978: Yes

Unit Information

  • Units in Building: 3

Lot Features

  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 3868sf

Financial Considerations

  • Parking Included: Yes
  • Assessment Year: 1914
  • Tax Amount: $18,260.96
  • Tax Year: 2025
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 14083040080000

Listed by Windy City Realty Corp.

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Listing agent

— 1461 W Winona St —

  • Windy City Realty Corp.

info@windycityrealty.com

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NMLS#: 1598647

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Be ready to buy your new home!

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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 1461 W Winona St

School District:Chicago Public School District 299
NameGradesDistance
Mccutcheon Elementary School
4865 North Sheridan Road, Chicago, IL 60640
PK-80.7 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 1461 W Winona St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/04/2026
Listed
$1,350,000
64.13%
MLS
8/10/2021
Sold
$822,500
—
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 1461 W Winona St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$13,925
—
$87,941
33%
2023
$13,925
3%
$66,000
—
2022
$13,575
2%
$66,000
—
2021
$13,272
7%
$66,000
19%
2020
$12,370
-1%
$55,528
-11%
2019
$12,535
2%
$62,392
—
2018
$12,325
13%
$62,392
23%
2017
$10,917
7%
$50,714
—
2016
$10,157
9%
$50,714
—
2015
$9,293
—
$50,714
2%
2014
$9,256
2%
$49,888
—
2013
$9,073
1%
$49,888
—
2012
$8,952
—
$49,888
—
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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Listed by Windy City Realty Corp.

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1461 W Winona Street, Chicago, IL 60640 (MLS# 12774861) is a Multi-Family property with 3 units containing 6 bedrooms and 0 full bathrooms. 1461 W Winona Street is currently listed for $1,350,000 and was received on October 04, 2026. Want to learn more about 1461 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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