1633 W Winona Street, Chicago, IL 60640 (MLS # 12789652)

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PRICE $1,500,000 dsIDX morgage calculator
BEDS 5
BATHS 3.5
HOME SIZE 3,000 sqft
LOT SIZE n/a

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."

DAYS ON MARKET 0 LAST UPDATED 10/21/2026
TRACT Andersonville YEAR BUILT 1905
COMMUNITY CHI - Uptown GARAGE SPACES 2.0
COUNTY Cook STATUS Active
PROPERTY TYPE(S) Single Family

SCHOOLS
School District Amundsen High School
Elementary School Mcpherson Elementary School
Jr. High School Mcpherson Elementary School
High School Amundsen High School


ADDITIONAL DETAILS
AIR Ceiling Fan(s), Central Air
AIR CONDITIONING Yes
APPLIANCES Dishwasher, Disposal, Dryer, Gas Cooktop, Humidifier, Microwave, Range, Range Hood, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
AREA CHI - Uptown
BASEMENT Finished, Full, Yes
CONSTRUCTION Brick
EXTERIOR Balcony
FIREPLACE Yes
GARAGE Yes
HEAT Radiant Floor, Zoned
INTERIOR Built-in Features, Entrance Foyer, High Ceilings, Walk-In Closet(s), Wet Bar
LOT 0
LOT DIMENSIONS 25 X 124
PARKING Garage Door Opener, Detached, Garage
SEWER Public Sewer
SUBDIVISION Andersonville
TAXES 15926.73
WATER Public
MORTGAGE CALCULATOR
   

TOTAL MONTHLY PAYMENT

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Listed with Fulton Grace Realty
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