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$1,500,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,000 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago
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Andersonville two-flat, reimagined as a single-family home. This one was taken down to the studs in a full 2023 rehab, so the big stuff is already done for you: new electrical, plumbing and gas lines, new windows, and a roof that is just over two years old with eight years of warranty left to transfer. What makes it special is what they saved. The original vintage woodwork was restored and vintage pieces were worked back into the design, so the home has the warmth of an older house with none of the old-house problems. Six bedrooms and three and a half baths give everybody room to spread out, with real options for a home office or guests. The primary suite has its own sitting area, a walk-in closet, and a bath with heated floors, separate vanities, and a large walk-in shower. The big front bedroom also has a sitting area, plus a private balcony looking out over the tree-lined street. Laundry is on the second floor, right where the bedrooms are, and Hunter Douglas cordless top-down, bottom-up shades are installed throughout. The main level is built for having people over. The open layout runs right into an eat-in kitchen centered on an oversized quartz island, with new countertops, a convection range, and a new dishwasher added in 2026. Up top there is a rooftop deck over the detached two-car garage, and out back a landscaped yard with a black porcelain tile patio that feels like a little escape. The lower level goes even further: a roomy recreation space plus a full kitchen added in 2026, so it works as a guest suite, an in-law setup, or the spot where everybody ends up on game day. Storage in both the garage and the basement. Steps from everything happening on Clark Street, and recently featured in Crain's "Before It Hits the Market."

Full Property Details for 1633 W Winona St

General

  • Price: $1,500,000
  • Taxes: $15,926 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12789652
  • Updated: 10/21/2026
  • Added to Site: 1 day(s) ago

Interior

  • Basement: Finished, F
  • Interior Features: Wet Bar, 1st-Floor Bedroom, Built-in Features, Walk-In Closet(s), High Ceilings, Historic/Period Mlwk, Separate Dining Room, Replacement Windows
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room, Electric
  • Appliances: Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Disposal, Stainless Steel Appliance(s), Wine Refrigerator, Range Hood, Gas Cooktop, Humidifier
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Basement Baths: Yes

Bedrooms

  • Total Bedrooms: 6
  • Bedrooms(Blw Grade): 1

Additional Information

  • Equipment: Ceiling Fan(s), Water Heater-Gas
  • Other Features: Commuter Bus, Commuter Train

Exterior

  • Exterior Features: Balcony, Roof Deck

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
  • Subdivision: Andersonville
  • Driving Directions: Ashland Ave North to Foster Ave West to Paulina South to Winona East to address

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299
  • Elementary School: Mcpherson Elementary School
  • Middle School: Mcpherson Elementary School
  • High School: Amundsen High School
  • Private School: Amundsen High School

Community

  • Assoc. Fees Include: None

Heating & Cooling

  • Cooling Type: Central Air Conditioning
  • Heating Type: Gas, Zoned, Radiant Floor

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • Basement Desc.: Finished, Full
  • Windows: Screens, Skylight(s)
  • Sub-Flooring: Hardwood
  • Square Feet: 3,000
  • Sq. Ft. Source: Plans
  • Year Built: 1905
  • Built Before 1978: Yes
  • Remodeled/Updated: 2024

Lot Features

  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 25 x 124

Financial Considerations

  • Parking Included: Yes
  • Assessment Year: 1905
  • Tax Amount: $15,926.73
  • Tax Year: 2025
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 14074080350000

Listed by Fulton Grace Realty

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Listing agents

— 1633 W Winona St —

  • Fulton Grace Realty

  • Fulton Grace Realty

jeffbushaw@fultongrace.com

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NMLS#: 1598647

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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 1633 W Winona St

School District:Chicago Public School District 299
NameGradesDistance
McPherson Elementary School
4728 North Wolcott Avenue, Chicago, IL 60640
K-80.5 mi
Amundsen High School
5110 North Damen Avenue, Chicago, IL 60625
9-120.5 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 1633 W Winona St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/21/2026
Listed
$1,500,000
9.89%
MLS
11/18/2024
Sold
$1,365,000
—
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 1633 W Winona St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$11,538
—
$82,272
42%
2023
$11,538
3%
$58,000
—
2022
$11,226
-4%
$58,000
—
2021
$11,663
4%
$58,000
15%
2020
$11,222
11%
$50,373
-11%
2019
$10,131
2%
$56,599
—
2018
$9,959
12%
$56,599
20%
2017
$8,855
3%
$47,210
—
2016
$8,598
10%
$47,210
—
2015
$7,827
15%
$47,210
15%
2014
$6,817
2%
$41,144
—
2013
$6,663
1%
$41,144
—
2012
$6,616
—
$41,144
—
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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1633 W Winona Street, Chicago, IL 60640 (MLS# 12789652) is a Single Family property with 6 bedrooms, 3 full bathrooms and 1 partial bathroom. 1633 W Winona Street is currently listed for $1,500,000 and was received on October 21, 2026. Want to learn more about 1633 W Winona Street? Do you have questions about finding other Single 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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