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$2,800,000
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Property Description
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.
Full Property Details
Full Property Details for 1029 N Winchester Ave
General
- Sold For: $2,800,000
- Taxes: (2024)
- Status: Closed
- Type: Multi-Family
- Source: MRED
- MLS ID: 12534356
- Added to Site: 121 day(s) ago
Interior
- Appliances: Humidifier
Rooms
Bathrooms
- Total Bathrooms: 7
- Bathroom Features: Separate Shower, Steam Shower, Double Sink, Soaking Tub
Bedrooms
- Total Bedrooms: 7
Additional Information
- Equipment: Cable TV, Carbon Monoxide Detectors
Exterior
- Exterior Features: Roof Deck
Parking
- Garage: Yes
- Garage Spaces: 3
- Total Spaces: 3
- Parking Features: Yes, Detached, Garage
Location
- Area: CHI - West Town
- County: Cook
- Driving Directions: Chicago Ave to Winchester North
School Information
- School District: 299
- Midd School District: 299
Heating & Cooling
- Heating Type: Natural Gas, Forced Air
Utilities
- Water: Lake Michigan
Structural Information
- Construction: Brick
- Exterior Const.: Brick
- Basement Desc.: None
- Year Built: 2025
Unit Information
- Units in Building: 3
Lot Features
- Lot Size Range: Standard Chicago Lot
- Lot Dimensions: 25 x 125
Financial Considerations
- Assessment Year: 2025
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Property ID: 17064140130000
Listed by Compass
Sold by Jameson Sotheby's Intl Realty
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Schools
Schools serving 1029 N Winchester Ave
School District:Chicago Public School District 299
| Name | Grades | Distance |
|---|---|---|
Pritzker Elementary School 2009 West Schiller Street, Chicago, IL 60622 | K-8 | 0.5 mi |
Wells Community Academy High School 936 North Ashland Avenue, Chicago, IL 60622 | 9-11 | 0.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1029 N Winchester Ave
Date
Details
Price
Change
Source
3/27/2026
Sold
$2,800,000
-3.44%
MLS
12/17/2025
Listed
$2,899,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1029 N Winchester Avenue, Chicago, IL 60612 (MLS# 12534356) is a Multi-Family property that was sold at $2,800,000 on March 27, 2026. Want to learn more about 1029 N Winchester Avenue? Do you have questions about finding other Multi-Family real estate for sale in West Town? You can browse all West Town real estate or contact a Coldwell Banker agent to request more information.

