1633 W Winona Street
Chicago, IL, 60640
$1,500,000
5 Beds
4 Baths
3,000 SqFt
0 Acres
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$1,500,000
1633 W Winona Street
Chicago, IL, 60640
MLS #MRD12789652 image #0
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.”

Property Details

Price:
$1,500,000
MLS #:
MRD12789652
Status:
Active
Beds:
5
Baths:
4
Type:
Single Family
Subdivision:
Andersonville
Neighborhood:
chiuptown
Listed Date:
Oct 21, 2026
Finished Sq Ft:
3,000
Year Built:
1905
Chi – UptownChiuptownAndersonvilleMcpherson Elementary SchoolMcpherson Elementary SchoolAmundsen High School

Schools

School District:
299
Elementary School:
Mcpherson Elementary School
Middle School:
Mcpherson Elementary School
High School:
Amundsen High School

Interior

Appliances
Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Disposal, Stainless Steel Appliance(s), Wine Refrigerator, Range Hood, Gas Cooktop, Humidifier
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1080
Cooling
Central Air
Fireplaces Total
1
Flooring
Hardwood
Heating
Gas, Zoned, Radiant Floor
Interior Features
Wet Bar, 1st Floor Bedroom, Built-in Features, Walk-In Closet(s), High Ceilings, Historic/Period Mlwk, Separate Dining Room, Replacement Windows
Laundry Features
Upper Level, In Unit, Sink

Exterior

Construction Materials
Brick
Exterior Features
Balcony, Roof Deck
Garage Spaces
2
Parking Features
Garage Door Opener, Yes, Garage Owned, Detached, Garage
Parking Spots
2
Parking Total
2
Patio And Porch Features
Deck
Window Features
Screens, Skylight(s)

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2025
Taxes
$15,927
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Debra Dobbs is one of Chicago’s top realtors with more than 42 years in the real estate business.

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Current real estate data for Single Family in Chicago as of Oct 25, 2026
2,753
Single Family Listed
69
Avg DOM
246
Avg $ / SqFt
$556,515
Avg List Price

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Property Summary

    Located in the Andersonville subdivision, 1633 W Winona Street Chicago IL is a Single Family for sale in Chicago, IL, 60640. It is listed for $1,500,000 and features 5 beds, 4 baths, and has approximately 3,000 square feet of living space, and was originally constructed in 1905. The current price per square foot is $500. The average price per square foot for Single Family listings in Chicago is $246. The average listing price for Single Family in Chicago is $556,515. To schedule a showing of MLS#mrd12789652 at 1633 W Winona Street in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
1633 W Winona Street
Chicago, IL