10188 S Winston Avenue
Chicago, IL, 60643
$499,000
6 Beds
3 Baths
0 SqFt
0 Acres
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$499,000
10188 S Winston Avenue
Chicago, IL, 60643
MLS #MRD12412967 image #0MLS #MRD12412967 image #1MLS #MRD12412967 image #2MLS #MRD12412967 image #3MLS #MRD12412967 image #4MLS #MRD12412967 image #5MLS #MRD12412967 image #6MLS #MRD12412967 image #7MLS #MRD12412967 image #8MLS #MRD12412967 image #9MLS #MRD12412967 image #10MLS #MRD12412967 image #11MLS #MRD12412967 image #12MLS #MRD12412967 image #13MLS #MRD12412967 image #14MLS #MRD12412967 image #15MLS #MRD12412967 image #16MLS #MRD12412967 image #17MLS #MRD12412967 image #18MLS #MRD12412967 image #19MLS #MRD12412967 image #20MLS #MRD12412967 image #21MLS #MRD12412967 image #22MLS #MRD12412967 image #23MLS #MRD12412967 image #24MLS #MRD12412967 image #25
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!

Property Details

Price:
$499,000
MLS #:
MRD12412967
Status:
Active Under Contract
Beds:
6
Baths:
3
Type:
Multi Family
Neighborhood:
CHI – Washington Heights
Listed Date:
Jul 7, 2025
Year Built:
1886
Chi – Washington HeightsChi – Washington Heights

Schools

School District:
299

Interior

Heating
Natural Gas

Exterior

Construction Materials
Vinyl Siding
Parking Features
On Site, Garage Owned, Detached, Garage
Parking Spots
5

Financial

Tax Year
2023
Taxes
$2,749
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Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

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Current real estate data for Multi Family in Chicago as of Sep 05, 2025
1,481
Multi Family Listed
82
Avg DOM
$499,086
Avg List Price

Community

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Property Summary

    10188 S Winston Avenue Chicago IL is a Multi Family for sale in Chicago, IL, 60643. It is listed for $499,000 To schedule a showing of MLS#mrd12412967 at 10188 S Winston Avenue in Chicago, IL, contact your Compass / The Debra Dobbs Group agent at 3123074909.
10188 S Winston Avenue
Chicago, IL