1252 W Winona Street #1
Chicago, IL, 60640
$650,000
2 Beds
3 Baths
2,100 SqFt
0 Acres
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$650,000
1252 W Winona Street #1
Chicago, IL, 60640
MLS #MRD12781698 image #0MLS #MRD12781698 image #1MLS #MRD12781698 image #2MLS #MRD12781698 image #3MLS #MRD12781698 image #4MLS #MRD12781698 image #5MLS #MRD12781698 image #6MLS #MRD12781698 image #7MLS #MRD12781698 image #8MLS #MRD12781698 image #9MLS #MRD12781698 image #10MLS #MRD12781698 image #11MLS #MRD12781698 image #12MLS #MRD12781698 image #13MLS #MRD12781698 image #14MLS #MRD12781698 image #15MLS #MRD12781698 image #16MLS #MRD12781698 image #17MLS #MRD12781698 image #18MLS #MRD12781698 image #19MLS #MRD12781698 image #20MLS #MRD12781698 image #21MLS #MRD12781698 image #22MLS #MRD12781698 image #23MLS #MRD12781698 image #24MLS #MRD12781698 image #25MLS #MRD12781698 image #26
Meticulously appointed duplex down in an intimate six unit building in a prime Andersonville location. Set on a quiet, tree lined street this two bedroom & 2.5 bath unit features high ceilings, hardwood floors, crown molding throughout. The main level offers a spacious living room anchored by a gas fireplace with built-ins on either side that flows in to the sunroom with windows on two sides that provides the perfect spot to relax. The separate dining room is just off the the fully renovated kitchen (2019), featuring two-tone cabinetry, a stone tile backsplash, and upgraded appliances. An office nook just off the kitchen offers a convenient work from home space and leads directly to a large deck. Both bedrooms are located on the main level, including a primary suite with a private en suite featuring dual sinks and a soaking tub. The spacious second bedroom and full hall bath complete the main floor. The lower level adds more living space with a family room, half bath, and laundry room with utility sink. Originally configured with a third bedroom, the lower level was opened up to create additional common living space, offering flexibility for a future owner to reimagine the layout. One exterior parking space is included in the price. Additional highlights include a newer furnace (2023) and a well run self managed association. Enjoy easy access to the lakefront, beaches, shopping, and dining along Clark & Argyle with buses, the Red Line and Lake Shore Drive blocks away. A wonderful blend of character & convenience in one of Chicago’s most sought after neighborhoods!

Property Details

Price:
$650,000
MLS #:
MRD12781698
Status:
Active
Beds:
2
Baths:
3
Type:
Condo
Neighborhood:
chiuptown
Listed Date:
Oct 15, 2026
Finished Sq Ft:
2,100
Year Built:
1919
Parking TotalChi – UptownChiuptownMccutcheon Elementary SchoolMccutcheon Elementary SchoolSenn High School

Schools

School District:
299
Elementary School:
Mccutcheon Elementary School
Middle School:
Mccutcheon Elementary School
High School:
Senn High School

Interior

Appliances
Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Flooring
Hardwood
Heating
Natural Gas, Forced Air, Radiant, Sep Heating Systems – 2+, Radiant Floor
Interior Features
Built-in Features, Walk-In Closet(s), Separate Dining Room
Laundry Features
Washer Hookup, Gas Dryer Hookup, In Unit, Sink

Exterior

Construction Materials
Brick
Parking Features
Off Alley, Assigned, Yes, Other
Parking Spots
1
Parking Total
1
Patio And Porch Features
Deck
Roof
Asphalt

Financial

HOA Fee
$395
HOA Fee Frequency
Monthly
HOA Includes
Water, Parking, Insurance, Exterior Maintenance, Scavenger, Snow Removal
Tax Year
2024
Taxes
$9,428
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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 Condo in Chicago as of Oct 18, 2026
3,213
Condo Listed
65
Avg DOM
376
Avg $ / SqFt
$637,605
Avg List Price

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Property Summary

    1252 W Winona Street #1 Chicago IL is a Condo for sale in Chicago, IL, 60640. It is listed for $650,000 and features 2 beds, 3 baths, and has approximately 2,100 square feet of living space, and was originally constructed in 1919. The current price per square foot is $310. The average price per square foot for Condo listings in Chicago is $376. The average listing price for Condo in Chicago is $637,605. To schedule a showing of MLS#mrd12781698 at 1252 W Winona Street #1 in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
1252 W Winona Street #1
Chicago, IL