Back 10188 S Winston Ave
Off Market

10188 S Winston Ave

Chicago IL 60643

6
3
5
Multi-Family
Last sold for $480,000
George FlannickGeorge Flannick, last sold this property on 16 September 2025 after 848 days on market.

Overview

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

6 bedrooms
3 bathrooms
5 carspaces
2 garage spaces
Multi-Family

Estimated Value

Based on this property and similar 6 bedroom multi families sold in Chicago over the last 12 months, the estimated median property value of 10188 S Winston Ave is $330k.

Median value
$330k
Estimated value range
$185k - $800k
Median days on market
11
Estimated value trend
-8%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Chicago. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 10188 S Winston Ave

2025
Sold
$480,000
16 Sep 2025 by George Flannick, of George Flannick

Happy sellers in Chicago

90%
90% of sellers in Chicago reported that their sale price either exceeded or met their price expectations.

Chicago stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 4 reviews in Chicago over the last 12 months.

Local market activity for 6 bedroom multi families in Chicago

In the last 12 months, 4 six-bedroom multi families similar to 10188 S Winston Ave, have been sold.

This represents a 25% decrease in six-bedroom multi families sales when compared to the previous 12 months.

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