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$1,595,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,068 Sq. Ft.
  • 2 Car Garage
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Space, character, and exceptional functionality come together in this stunning 5-bedroom, 3.5-bath home in the heart of Lincoln Square. Thoughtfully redesigned in a complete 2016 gut renovation, this home sits on an oversized lot and offers the perfect balance of everyday comfort and effortless entertaining. The main level features a bright, open floor plan where the living and dining areas flow seamlessly into the chef's kitchen and family room. Designed for gathering, the eat-in kitchen showcases quartz countertops, premium Thermador appliances, a generous island, and a wet bar. Rich hardwood floors, custom millwork, and elegant coffered ceilings add timeless sophistication throughout the space, while a convenient mudroom and French-style sliding doors leading to the deck complete the main floor.Upstairs, retreat to the spacious primary suite featuring a large walk-in closet and a spa-inspired bath with a freestanding soaking tub, separate glass-enclosed shower, and radiant heated floors. Two additional generously sized bedrooms, a full bath, and one of the home's two laundry areas complete the second level. The finished lower level offers incredible flexibility with a spacious recreation room, two additional bedrooms, a full bath, and a second laundry room, making it ideal for guests, a home office, gym, or playroom. Perfectly located just steps from Winnemac Park and within walking distance of Lincoln Square's beloved restaurants, cafes, and boutiques, this exceptional home offers the space, style, and location you've been waiting for.

Full Property Details for 2237 W Winona St

General

  • Price: $1,595,000
  • Taxes: $28,545 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12709262

Rental Information

  • Complex Features: Park, Tennis Court(s), Sidewalks, Street Lights

Interior

  • Basement: Finished, F
  • Interior Features: Wet Bar, Built-in Features, Walk-In Closet(s), Coffered Ceiling(s), Open Floorplan, Special Millwork, Pantry, Quartz Counters
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room
  • Appliances: Range, Microwave, Dishwasher, High-End Refrigerator, Disposal, Stainless Steel Appliance(s), Range Hood
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Basement Baths: Yes
  • Bathroom Features: Separate Shower, Double Sink, Garden Tub

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms(Blw Grade): 2

Additional Information

  • Equipment: Sump Pump
  • Other Features: Commuter Bus

Parking

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

Location

  • Area: CHI - Lincoln Square
  • County: Cook
  • Township: Lake View
  • Driving Directions: North on Leavitt to Winona, West to Property.

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299
  • Elementary School: Chappell Elementary School
  • Middle School: Chappell 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: Natural Gas, Forced Air

Utilities

  • Sewer: Public Sewer
  • Water: Lake Michigan

Structural Information

  • Construction: Vinyl Siding, Brick
  • Exterior Const.: Vinyl Siding, Brick
  • Basement: Yes
  • Basement Desc.: Finished, Full
  • Sub-Flooring: Hardwood
  • Square Feet: 3,068
  • Sq. Ft. Source: Plans
  • Built Before 1978: Yes
  • Remodeled/Updated: 2016

Lot Features

  • Lot Size Range: Oversized Chicago Lot
  • Lot Dimensions: 29 x 132

Financial Considerations

  • Parking Included: Yes
  • Tax Amount: $28,545.91
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: List Broker Must Accompany
  • Property ID: 14073050150000

Listed by Compass

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— 2237 W Winona St —

  • Compass

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NMLS#: 1598647

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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 2237 W Winona St

School District:Chicago Public School District 299
NameGradesDistance
Chappell Elementary School, Chicago, IL
2135 West Foster Avenue, Chicago, IL 60625
PK-80.1 mi
Amundsen High School
5110 North Damen Avenue, Chicago, IL 60625
9-120.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Tax History for 2237 W Winona St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$21,215
—
$145,379
40%
2023
$21,215
3%
$103,866
—
2022
$20,660
-6%
$103,866
-8%
2021
$22,054
11%
$113,000
22%
2020
$19,919
1%
$92,516
-9%
2019
$19,737
-5%
$101,666
-7%
2018
$20,863
3%
$109,052
15%
2017
$20,327
136%
$94,426
120%
2016
$8,598
9%
$42,927
—
2015
$7,866
20%
$42,927
13%
2014
$6,561
2%
$37,931
—
2013
$6,420
6%
$37,931
—
2012
$6,039
—
$37,931
—
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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2237 W Winona Street, Chicago, IL 60625 (MLS# 12709262) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 2237 W Winona Street is currently listed for $1,595,000 and was received on July 23, 2026. Want to learn more about 2237 W Winona Street? Do you have questions about finding other Single Family real estate for sale in Lincoln Square? You can browse all Lincoln Square real estate or contact a Coldwell Banker agent to request more information.

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