5042 W Winnemac Avenue
Chicago, IL, 60630
$499,000
3 Beds
3 Baths
0 SqFt
0 Acres
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$499,000
5042 W Winnemac Avenue
Chicago, IL, 60630
MLS #MRD12628249 image #0MLS #MRD12628249 image #1MLS #MRD12628249 image #2MLS #MRD12628249 image #3MLS #MRD12628249 image #4MLS #MRD12628249 image #5MLS #MRD12628249 image #6MLS #MRD12628249 image #7MLS #MRD12628249 image #8MLS #MRD12628249 image #9MLS #MRD12628249 image #10MLS #MRD12628249 image #11MLS #MRD12628249 image #12MLS #MRD12628249 image #13MLS #MRD12628249 image #14MLS #MRD12628249 image #15MLS #MRD12628249 image #16MLS #MRD12628249 image #17MLS #MRD12628249 image #18MLS #MRD12628249 image #19MLS #MRD12628249 image #20
Open House May 02, 2026
11:00 – 01:00
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.

Property Details

Price:
$499,000
MLS #:
MRD12628249
Status:
Active
Beds:
3
Baths:
3
Type:
Multi Family
Neighborhood:
chiforestglen
Listed Date:
Apr 29, 2026
Year Built:
1928
Chi – Forest GlenChiforestglen

Schools

School District:
299

Interior

Heating
Natural Gas

Exterior

Construction Materials
Brick
Garage Spaces
2
Parking Features
Garage Door Opener, Yes, Garage Owned, Detached, Garage
Parking Spots
2
Parking Total
2
Roof
Asphalt

Financial

Tax Year
2023
Taxes
$6,757
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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 May 02, 2026
1,356
Multi Family Listed
78
Avg DOM
$513,577
Avg List Price

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Property Summary

    5042 W Winnemac Avenue Chicago IL is a Multi Family for sale in Chicago, IL, 60630. It is listed for $499,000 To schedule a showing of MLS#mrd12628249 at 5042 W Winnemac Avenue in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
5042 W Winnemac Avenue
Chicago, IL