1029 North Winchester Avenue

Chicago IL 60622

Multi-Family

Last sold for $2,800,000

Melanie Giglio, last sold this property on 27 March 2026 after 98 days on market.

Overview

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.

Features

7 bedrooms

7 bathrooms

3 carspaces

3 garage spaces

Multi-Family

Estimated Value

Based on this property and similar 7 bedroom multi families sold in Chicago over the last 12 months, the estimated median property value of 1029 North Winchester Avenue is $1.13m.

Median value

$1.13m

Estimated value range

$619k - $2.8m

Median days on market

Estimated value trend

37%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Chicago. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1029 North Winchester Avenue

2026

Sold

$2,800,000

27 Mar 2026 by Melanie Giglio, of Compass

2007

Sold

$640,000

27 Oct 2007 by Patricia Blagojevich, of River Realty, Inc.

Happy sellers in Chicago

We have insufficient information to provide an overview of customer satisfaction for Chicago. Viewing the agent profiles, reviews and sales for Chicago can provide insights for this location.