1029 N Winchester Avenue
Chicago, IL, 60612
$2,899,900
7 Beds
7 Baths
0 SqFt
0 Acres
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$2,899,900
1029 N Winchester Avenue
Chicago, IL, 60612
MLS #MRD12534356 image #0MLS #MRD12534356 image #1MLS #MRD12534356 image #2MLS #MRD12534356 image #3MLS #MRD12534356 image #4MLS #MRD12534356 image #5MLS #MRD12534356 image #6MLS #MRD12534356 image #7MLS #MRD12534356 image #8MLS #MRD12534356 image #9MLS #MRD12534356 image #10MLS #MRD12534356 image #11MLS #MRD12534356 image #12MLS #MRD12534356 image #13MLS #MRD12534356 image #14MLS #MRD12534356 image #15MLS #MRD12534356 image #16MLS #MRD12534356 image #17MLS #MRD12534356 image #18MLS #MRD12534356 image #19MLS #MRD12534356 image #20MLS #MRD12534356 image #21MLS #MRD12534356 image #22MLS #MRD12534356 image #23MLS #MRD12534356 image #24MLS #MRD12534356 image #25MLS #MRD12534356 image #26
Introducing a rare opportunity to own an exceptional, brand-new three-unit all-brick building in the heart of Wicker Park offering a total of 7 bedrooms + office, unmatched outdoor spaces, premium finishes, and an A+ location. Thoughtfully designed with cohesive high-end aesthetics throughout, each residence features custom Scandinavian-inspired cabinetry, quartz countertops, designer lighting, and top-tier Thermador appliances, creating a seamless blend of luxury and modern functionality. The duplex-down (Unit 1) offers 3 bedrooms and 2.5 baths with all bedrooms on one level, an expansive main floor with floor-to-ceiling west-facing windows, a large family room that opens directly to a private terrace, and an additional private garage rooftop deck or you can give it to the middle unit because it already has massive outdoor space right off the living room. The simplex (Unit 2) features 2 bedrooms and 2 baths, an open-concept living space, abundant natural light, and impressive private outdoor space ideal for entertaining or relaxing. The duplex-up penthouse (Unit 3) includes 2 bedrooms, 2 baths, plus a dedicated office, soaring ceiling heights, and a private rooftop deck with breathtaking city views, an incredible extension of your living space. Perfectly positioned just steps from everything Wicker Park and Division Street have to offer: boutique shopping, award-winning dining, vibrant nightlife, and the Ashland Blue Line (0.6 miles). Situated in the coveted Pritzker School District with low assessments, this building is an exceptional opportunity for owners, investors, or those seeking a live-plus-rent lifestyle. Delivery expected end of Dec 2025. Urban luxury living at its finest.

Property Details

Price:
$2,899,900
MLS #:
MRD12534356
Status:
Active
Beds:
7
Baths:
7
Type:
Multi Family
Neighborhood:
chiwesttown
Listed Date:
Dec 17, 2025
Year Built:
2025
NewconstructionChi – West TownChiwesttown

Schools

School District:
299

Interior

Appliances
Humidifier
Heating
Natural Gas, Forced Air

Exterior

Construction Materials
Brick
Exterior Features
Roof Deck
Parking Features
Yes, Detached, Garage
Parking Spots
3

Financial

Tax Year
2024
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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 Multi Family in Chicago as of Dec 19, 2025
1,346
Multi Family Listed
89
Avg DOM
$483,956
Avg List Price

Community

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Property Summary

    1029 N Winchester Avenue Chicago IL is a Multi Family for sale in Chicago, IL, 60612. It is listed for $2,899,900 To schedule a showing of MLS#mrd12534356 at 1029 N Winchester Avenue in Chicago, IL, contact your Compass / The Debra Dobbs Group agent at 3123074909.
1029 N Winchester Avenue
Chicago, IL