5042 W Winnemac Avenue — Chicago, IL 60630
Closed
Chicago, IL 60630

5042 W Winnemac Avenue

$499,000
3 beds · 3 baths
Listed at $499,000 6 days on market $6,757/yr taxes
01About 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.

02Inside the home
03By the numbers
$499,000
List price
Square feet
3
Bedrooms
3
Bathrooms
1928
Year built
Lot size
2
Garage spaces
$6,757
Annual taxes
Two to Four Units
Style
6
Days on market
04Features
Heating
Natural Gas
Parking
Garage Door OpenerGarage OwnedDetachedGarage
Construction
Brick
Sewer
Public Sewer
05Neighborhood
  • Rabbit’s Bar and Grill 0.2 mi
  • Bust Outs 0.2 mi
  • Subway 0.3 mi
  • Chipotle 0.4 mi
  • Jollibee 0.4 mi
  • Teriyaki Madness 0.4 mi
  • Mobil Mart 0.3 mi
  • Eden's Food and Liquors 0.3 mi
  • BP Shop 0.3 mi
  • Marathon 0.4 mi
  • Seafood City 0.4 mi
  • 7-Eleven 0.4 mi
  • Roberts Square Park 0.3 mi
  • Forest Glen Park 0.3 mi
  • Grace Zwiefka Thuis Park 0.3 mi
  • Ashmore Park 0.4 mi
  • Jefferson Memorial Park 0.6 mi
  • North Mayfair Park 0.6 mi
  • Dunkin' 0.3 mi
  • Red Ribbon 0.4 mi
  • Starbucks 0.4 mi
  • Mr. B's Caribbean Grill 0.5 mi
  • Dunkin' 0.5 mi
  • Weston's Coffee & Tap Co. 0.5 mi
POI data via Mapbox · OpenStreetMap contributors
06History

Every event we have for this address, straight from the MLS.

Jun 3, 2026
SoldThis listing
$525,000
Apr 29, 2026
Listed for saleThis listing
Compass
$499,000
Sourced from MRED. Older events appear here as our history backfill completes.
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08See it for yourself

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09Similar homes
Listed by Compass · Elias Masud
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12628249
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