5042 W Winnemac Avenue
Chicago, IL, 60630 $ 499,000
Bedrooms3 Baths3.0 Monthly Estimate*
$ 3,072
for $499,000 with 3 bedrooms and 3 full baths. This home was built in 1928.
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.
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FeaturesGeneralSewer Public Sewer
Heating Natural Gas
Possession Closing
Roof Asphalt
Garage Spaces 2
Construction Materials Brick
Year Built 1928
Township Jefferson
Tax Year 2023
Ownership Fee Simple
Gross Income 16800
County Cook
New Construction N
Property Type Residential Income Two to Four Units
Contingency Attorney/Inspection
Total Rooms 12
Status Contingent
Directions Foster to Laramie. South on Laramie to Winnemac. East on Winnemac to property.
City Chicago
High School District 299
MLS Area CHI - Forest Glen
Tax Annual Amount 6757
Trash Expense 19
Standard Status Active Under Contract
Middle/Junior School District 299
Elementary School District 299
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InteriorBasement Finished Full
Total Bedrooms 3
Total Baths 3
Bedrooms Possible 3
Bathroom Soaking Tub
Full Baths Building 3
Half Baths Building 0
Total Number of Units 2
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ExteriorParking Features Garage Door Opener Yes Garage Owned Detached Garage
Water Source Lake Michigan Public
Total Parking 2
Lot Dimensions 25X125
Waterfront Y/N N
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* Excluded FeaturesList Byeli@secondcityagents.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $3,072
- Monthly Property Taxes
- $563
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbyMulti-family listings in Chicago, IL
Average List Price $613,490
Percent of Sale Price 23%
About Chicago, IL 2,755,380 Population
-4% Since 2002
$ 53,088 Median Income
36.07 Median Age
25% Households with Children
Trends Information provided by ATTOM Data Solutions.
566059 Elementary School
566846 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 4/29/2026 | $499,000 | | Listed Price |