$899,900
1355 W Winnemac Avenue #3
Chicago, IL, 60640
Meticulously maintained and perfectly positioned, this rare 3BD/2BA simplex penthouse in the heart of Andersonville offers the ultimate blend of modern luxury and expansive private outdoor living. Built in 2018, this all-brick residence retains its “like-new” luster with high-end finishes and an intelligent, open-concept layout. The light-filled interior features a stunning living area anchored by a gas fireplace, flowing into a chef’s kitchen with premium Thermador appliances and a dedicated dining space. Step out onto the wide front balcony to enjoy morning coffee overlooking a quiet, tree-lined one-way street. The primary suite is a true retreat, featuring a private back balcony, a large walk-in closet, and a spa-inspired ensuite bath with heated floors and steam shower. Two additional generous bedrooms are located on the main level. Ascend to the versatile upper-level bonus space-ideal for a high-performance home office-which opens to a massive private rooftop deck with breathtaking, unobstructed views of the Chicago skyline. This location is a commuter’s dream, offering effortless access to both the Red Line and the UP-N Metra, placing the entire city within reach. Includes 1 garage space and storage. This is a pristine, move-in-ready asset in one of Chicago’s most coveted walk-to-everything pockets.
Property Details
Price:
$899,900
MLS #:
MRD12592014
Status:
Active Under Contract
Beds:
3
Baths:
2
Type:
Single Family
Neighborhood:
chiuptown
Listed Date:
Mar 16, 2026
Year Built:
2018
Schools
School District:
299
Elementary School:
Mccutcheon Elementary School
Middle School:
Mcclellan Elementary School
High School:
Senn High School
Interior
Appliances
Microwave, Dishwasher, High End Refrigerator, Washer, Dryer, Stainless Steel Appliance(s)
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Fireplaces Total
1
Flooring
Hardwood
Heating
Natural Gas, Forced Air, Radiant Floor
Interior Features
Storage, Walk-In Closet(s), Dining Combo, Pantry
Laundry Features
In Unit
Exterior
Construction Materials
Brick
Garage Spaces
1
Parking Features
Garage Door Opener, Yes, Detached, Garage
Parking Spots
1
Parking Total
1
Financial
HOA Fee
$190
HOA Fee Frequency
Monthly
HOA Includes
Water, Insurance, Exterior Maintenance, Scavenger
Tax Year
2024
Taxes
$15,422
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 Apr 10, 2026
2,718
Single Family Listed
68
Avg DOM
232
Avg $ / SqFt
$559,412
Avg List Price
Community
- Address1355 W Winnemac Avenue #3 Chicago IL
- CityChicago
- CountyCook
- Zip Code60640
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Property Summary
- 1355 W Winnemac Avenue #3 Chicago IL is a Single Family for sale in Chicago, IL, 60640. It is listed for $899,900 and features 3 beds, 2 baths, and has approximately 0 square feet of living space, and was originally constructed in 2018. The average price per square foot for Single Family listings in Chicago is $232. The average listing price for Single Family in Chicago is $559,412. To schedule a showing of MLS#mrd12592014 at 1355 W Winnemac Avenue #3 in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.

Copyright 2026. All rights reserved.
1355 W Winnemac Avenue #3
Chicago, IL





