Chicago, IL 60630 5042 W Winnemac Avenue

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Presented By: Compass
  • MLS# 12628249
  • 04/29/2026
  • Request Tour
  • Request Info
  • Beds • 3
  • Baths • 3
  • Garage • 2

Home Details

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.
Presented By: Compass

Interior Features for 5042 W Winnemac Avenue

Bedrooms

Bedrooms Possible3
Total Bedrooms3

Bathrooms

BathroomSoaking Tub
Full Baths Building3
Half Baths Building
Total Baths3

Other Interior Features

BasementFinished, Full
Total Number of Units2

General for 5042 W Winnemac Avenue

CityChicago
Construction MaterialsBrick
ContingencyAttorney/Inspection
CountyCook
DirectionsFoster to Laramie. South on Laramie to Winnemac. East on Winnemac to property.
Elementary School District299
Garage Spaces2
Gross Income16800
HeatingNatural Gas
High School District299
MLS AreaCHI - Forest Glen
Middle/Junior School District299
New ConstructionNo
OwnershipFee Simple
PossessionClosing
Property TypeResidential Income
Property TypeTwo to Four Units
RoofAsphalt
SewerPublic Sewer
Standard StatusActive Under Contract
StatusContingent
Tax Annual Amount6757
Tax Year2023
Total Rooms12
TownshipJefferson
Trash Expense19
Year Built1928

Exterior for 5042 W Winnemac Avenue

BuyerOfficeFax(312) 525-9660
Lot Dimensions25X125
OwnerPhone999-999-9999
Parking FeaturesGarage Door Opener, Yes, Garage Owned, Detached, Garage
Total Parking2
Water SourceLake Michigan, Public
Waterfront Y/NNo

Additional Details

Price History

Client Care

Price $499,000
MLS#12628249
List Date 04/29/2026
Property Type Contingent
Phone 847.485.2500
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Request Info
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