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$525,000
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Property Description
Step into timeless elegance at 5042 W Winnemac Ave, a meticulously renovated all-brick 1929 Jefferson Park 2-flat that masterfully fuses historic charm with contemporary luxury. This property is a rare gem, offering two distinct units that cater to both multi-generational living and investment opportunities. Every detail has been thoughtfully designed to create a harmonious blend of historic character and modern convenience. First-Floor Duplex-Down (Unit 1) The main level and fully reimagined lower level of Unit 1 provide a sophisticated sanctuary with 2 bedrooms and 2 baths. The living room, featuring custom built-ins and freshly painted walls, exudes warmth and charm. Gleaming hardwood floors flow throughout the first floor, which also includes a versatile exercise room that can double as a private office. The gourmet kitchen is a chef's dream, complete with granite countertops, stainless steel appliances, and crisp white cabinetry that enhances the bright and airy feel of the space. The first-floor bathroom features a tub and shower combo, an updated vanity, and a modernized design. The fully renovated basement bathroom offers a luxurious glass-enclosed shower with subway tile and a sleek, contemporary aesthetic. The fully renovated lower level also boasts new laminate vinyl plank flooring and features a spacious family room and additional living space. Step outside to your private yard oasis, perfect for entertaining or relaxing, and enjoy the convenience of in-unit laundry. Attic Penthouse (Unit 2) Unit 2 is a light-filled 1-bedroom, 1-bath penthouse that combines charm and functionality. The eat-in kitchen features white cabinetry, butcher block countertops, and a stainless steel stove, creating a clean and modern aesthetic. While hardwood floors are found in several rooms, the hallway and kitchen feature alternate flooring for added practicality. The bathroom is a serene retreat, complete with a soaker tub, elegant millwork, and white cabinetry. The convenience of a washer/dryer combo enhances everyday living, making this unit as versatile as it is beautiful. Located in the prestigious Jefferson Park neighborhood, this property offers unparalleled convenience for commuters and city explorers alike. The home is just a short walk to the Jefferson Park Transit Center, providing access to the Blue Line train, Metra rail, and multiple bus routes, making travel to downtown Chicago and beyond a breeze. For drivers, the property is ideally situated near the Kennedy Expressway (I-90) and the Edens Expressway (I-94), offering quick and easy access to major highways. Whether you're heading to O'Hare International Airport, downtown Chicago, or the suburbs, this location ensures seamless connectivity. The 2-car garage is a standout feature, with its very tall ceilings that can easily accommodate a work van or truck, making it ideal for professionals or those with larger vehicles. The property is equipped with dual furnaces (2018/2005) and a 2015 water heater, ensuring comfort and efficiency year-round. This property is a true masterpiece, offering a unique opportunity to own a home that combines historic charm, modern updates, and exceptional functionality. Whether you're seeking a luxurious multi-generational home or a prime investment property, 5042 W Winnemac Ave delivers on every level. Don't miss your chance to experience the pinnacle of refined living, schedule your private showing today.
Full Property Details
Full Property Details for 5042 W Winnemac Ave
General
- Sold For: $525,000
- Taxes: $6,757 (2023)
- Status: Closed
- Type: Multi-Family
- Source: MRED
- MLS ID: 12628249
- Added to Site: 57 day(s) ago
Rooms
Bathrooms
- Total Bathrooms: 3
- Bathroom Features: Soaking Tub
Bedrooms
- Total Bedrooms: 3
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Features: Garage Door Opener, Yes, Garage Owned, Detached, Garage
Location
- Area: CHI - Forest Glen
- County: Cook
- Driving Directions: Foster to Laramie. South on Laramie to Winnemac. East on Winnemac to property.
School Information
- School District: 299
- Midd School District: 299
Heating & Cooling
- Heating Type: Natural Gas
Utilities
- Water: Lake Michigan, Public
Structural Information
- Construction: Brick
- Exterior Const.: Brick
- Basement Desc.: Finished, Full
- Roof: Asphalt
- Year Built: 1928
- Built Before 1978: Yes
Unit Information
- Units in Building: 2
Lot Features
- Lot Size Range: Less than .25 Acre
- Lot Dimensions: 25 x 125
Financial Considerations
- Parking Included: Yes
- Assessment Year: 1928
- Tax Amount: $6,757
- Tax Year: 2023
Disclosures and Reports
- Ownership: Fee Simple
- Property ID: 13094090260000
Listed by Compass
Sold by Chicago Properties Firm
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Schools
Schools serving 5042 W Winnemac Ave
School District:Chicago Public School District 299
| Name | Grades | Distance |
|---|---|---|
Beaubien Elementary School 5025 North Laramie Avenue, Chicago, IL 60630 | PK-8 | 0.1 mi |
Taft High School 6530 West Bryn Mawr Avenue, Chicago, IL 60631 | 9-12 | 2.1 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 5042 W Winnemac Ave
Date
Details
Price
Change
Source
6/03/2026
Sold
$525,000
5.21%
MLS
4/29/2026
Listed
$499,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
5042 W Winnemac Avenue, Chicago, IL 60630 (MLS# 12628249) is a Multi-Family property that was sold at $525,000 on June 03, 2026. Want to learn more about 5042 W Winnemac Avenue? Do you have questions about finding other Multi-Family real estate for sale in Chicago? You can browse all Chicago real estate or contact a Coldwell Banker agent to request more information.

