2237 W Winona Street
Chicago, IL, 60625
$1,575,000
3 Beds
4 Baths
3,068 SqFt
0 Acres
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$1,575,000
2237 W Winona Street
Chicago, IL, 60625
MLS #MRD12765309 image #0MLS #MRD12765309 image #1MLS #MRD12765309 image #2MLS #MRD12765309 image #3MLS #MRD12765309 image #4MLS #MRD12765309 image #5MLS #MRD12765309 image #6MLS #MRD12765309 image #7MLS #MRD12765309 image #8MLS #MRD12765309 image #9MLS #MRD12765309 image #10MLS #MRD12765309 image #11MLS #MRD12765309 image #12MLS #MRD12765309 image #13MLS #MRD12765309 image #14MLS #MRD12765309 image #15MLS #MRD12765309 image #16MLS #MRD12765309 image #17MLS #MRD12765309 image #18MLS #MRD12765309 image #19MLS #MRD12765309 image #20MLS #MRD12765309 image #21MLS #MRD12765309 image #22MLS #MRD12765309 image #23MLS #MRD12765309 image #24MLS #MRD12765309 image #25MLS #MRD12765309 image #26MLS #MRD12765309 image #27MLS #MRD12765309 image #28MLS #MRD12765309 image #29
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. Quick close possible.

Property Details

Price:
$1,575,000
MLS #:
MRD12765309
Status:
Active
Beds:
3
Baths:
4
Type:
Single Family
Neighborhood:
chilincolnsquare
Listed Date:
Sep 21, 2026
Finished Sq Ft:
3,068
TennisChi – Lincoln SquareChilincolnsquareChappell Elementary SchoolChappell Elementary SchoolAmundsen High School

Schools

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

Interior

Appliances
Range, Microwave, Dishwasher, High End Refrigerator, Disposal, Stainless Steel Appliance(s), Range Hood
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1192
Cooling
Central Air
Fireplaces Total
1
Flooring
Hardwood
Heating
Natural Gas, Forced Air
Interior Features
Wet Bar, Built-in Features, Walk-In Closet(s), Coffered Ceiling(s), Open Floorplan, Special Millwork, Pantry, Quartz Counters
Laundry Features
Upper Level, Multiple Locations

Exterior

Community Features
Park, Tennis Court(s), Sidewalks, Street Lights
Construction Materials
Vinyl Siding, Brick
Garage Spaces
2
Parking Features
Garage Door Opener, Yes, Garage Owned, Detached, Garage
Parking Spots
2
Parking Total
2
Patio And Porch Features
Deck

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2024
Taxes
$28,546
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Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

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Current real estate data for Single Family in Chicago as of Sep 29, 2026
2,764
Single Family Listed
69
Avg DOM
244
Avg $ / SqFt
$557,814
Avg List Price

Community

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Property Summary

    2237 W Winona Street Chicago IL is a Single Family for sale in Chicago, IL, 60625. It is listed for $1,575,000 and features 3 beds, 4 baths, and has approximately 3,068 square feet of living space.The current price per square foot is $513. The average price per square foot for Single Family listings in Chicago is $244. The average listing price for Single Family in Chicago is $557,814. To schedule a showing of MLS#mrd12765309 at 2237 W Winona Street in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
2237 W Winona Street
Chicago, IL