Active
5042 Winnemac Avenue
Chicago, IL 60630
$499,000
3beds
3baths
—sqft
Anything from "is it priced right?" to "what's the catch?"
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About this home
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.
MLS Description — as provided by the listing brokerage.
Location
The facts
Property typeResidential Income
Year built1928
Age band91-100 Years
Garage spaces2
Total parking2
Lot dimensions25X125
AreaCHI - Forest Glen
Bedrooms (total)3
Annual tax$6,757
First listedApr 29, 2026
Parcel #13094090260000
CountyCook
MLS #MRD12628249
Days on market1
Photos21
Features
Heating
Natural Gas
Parking
Garage Door OpenerYesGarage OwnedDetachedGarage
Construction
Brick
Sewer
Public Sewer
Mentioned in description
dwello's AI pulled these details from the agent's listing description. Each is a direct quote — verify anything critical with the agent.
- ✨ Hardwood Floors “Gleaming hardwood floors flow throughout the first floor”
- ✨ Finished Basement “The fully renovated lower level also boasts new laminate vinyl plank flooring and features a spacious family room and additional living space”
- ✨ Updated Kitchen “The gourmet kitchen is a chef's dream, complete with granite countertops, stainless steel appliances, and crisp white cabinetry”
- ✨ Recent Roof/HVAC/Windows “The property is equipped with dual furnaces (2018/2005) and a 2015 water heater”
Listed by
Compass
Elias Masud
Listing courtesy of mred MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID as of 4/29/2026, 6:22:03 PM. All data should be independently verified.
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