10188 South Winston, Chicago IL 60643
- Units 3
- Total Beds 6
- Total Baths 3
- Taxes $2,749.34
- Payment Estimate View Mortgage Calculator
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Property Description
Discover Exceptional Living & Investment in This Fully Renovated, Owner-Occupant Gem! Welcome to 10188 S. Winston Ave, Chicago IL in lovely Longwood Manor, steps away from the historic Beverly Neighborhood. 10188 S. Winston is a truly remarkable opportunity to purchase a completely renovated 3 unit building while immediately beginning to generating income. This magnificent building, fully renovated from top to bottom, presents a unique layout featuring two spacious, independent units complemented by an additional private in-law apartment. Every detail has been thoughtfully updated, offering a seamless "move-in ready" experience. The upper unit is a 1,243sf 3 bedroom, one bath unit with washer and dryer in unit. First floor duplex down is a 968sf 2 bedroom and 1 bathroom, and the inlaw is a 675sf 1 bedroom 1 bathroom unit. All have separate entrances and egresses. All units have separate electric and gas meters. The building has one water meter. Step inside to find gleaming new flooring throughout, freshly applied paint in a contemporary palette, and kitchens boasting a full suite of brand-new appliances that elevate both style and functionality. Beyond the aesthetics, enjoy complete peace of mind with all new mechanicals and new roof, ensuring years of worry-free ownership. Beyond the stunning interiors, this property truly shines with its generous outdoor space. A large back and side lot offers ample room for recreation, gardening, or future expansion possibilities. Parking is an absolute breeze with a two-car garage and an additional three-car off-street parking area, providing abundant space for residents and guests alike. This isn't just a house; it's a meticulously crafted home and a smart investment awaiting its new owner. You truly must see it to appreciate the quality and care that has gone into every corner. Don't miss your chance to secure this unparalleled opportunity all with a convenient location in this rapidly gentrifying bedroom community!
Features & Information
Key Details
- List Price $499,000
- Property Taxes $2,749.34
- Price/ Sq. Ft. Unavailable
- Year Built 1886
- Parking Type Garage,Space/s
- Status Active
Rooms
- Total Rooms 15
- Basement F
Exterior Features
-
Parking
- Parking Details Garage,Space/s
- # of Cars: 5
Building Information
- Number of Units 3
- Age of Building 100+ Years
- Exterior Construction Vinyl Siding
- Heating & Cooling Gas
-
Units
- Unit 1 Stove, Refrigerator, Washer, Dryer, Microwave
- Unit 2 Stove, Refrigerator, Washer, Dryer, Dishwasher, Microwave
- Unit 3 Stove, Refrigerator, Washer, Dryer, Microwave
Location
- County Cook
- Township Hyde Park
- Corporate Limits Chicago
- Directions to Property South To 101st Street Left On Winston Ave
-
Schools
- Elementary School District 299
- Junior High District 299
- High School District: 299
-
Property Taxes
- Tax 2749.34
- Tax Year 2023
- Parcel Identification Number 25083080760000
Utilities
- Sewer Sewer-Publ
Listed by George Flannick for George Flannick | Source: MRED as distributed by MLS GRID
Based on information submitted to the MLS GRID as of 7/15/2025 11:32 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Explore Longwood Manor
Small in acreage but big on character, Longwood Manor is home to some of the most historic houses on Chicago's south side. Like its neighboring communities of Brainerd and Washington Heights, Longwood Manor built an identity based on working-class traditions tied to the once-thriving railroad industry and an immigrant past that still defines much of the area's legacy to this day. Community parks and recreation facilities provide residents with ample room for exercise, play, sports and amusement. In addition to housing the usual tennis courts and baseball fields, the parks in Longwood Manor host free live music concerts and movie screenings. The rest of the neighborhood encompasses long blocks of classic Chicago bungalows and a few rib houses and seafood shacks for the best in southern-style cooking.
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