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
BEDROOMS
6
BATHROOMS
3
SQFT
N/A
YEAR BUILT
1886
PARKING SPOTS
2
MLS #
12412967
FULL ADDRESS
10188 10188 Winston Avenue
CITY
Chicago, IL
ZIP
60643

Listing Details

Listing Office
George Flannick
Listing Agent
George Flannick
Contact
773-372-2055
Last Data Update
2025-09-21T08:05:30Z

Interior

BATHROOMS
3 Full Bathrooms

Schools

School District
299
Elementary School
High School

Buy This Home With a Local Expert

22 years. 600+ Chicago closings. Individual, hands-on representation from first tour through close. Ken can be your buyer's agent on this property. Call 773.398.5585 or drop your details below.

MRED Logo
IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by MRED (Midwest Real Estate Data). Properties may or may not be listed by the office/agent presenting the information.

Some listings have been excluded from this website.

© 2026 At World Properties, LLC. All rights reserved

Other listings you might like

Let’s start the conversation!

Whether you’re buying, selling, or just exploring your options. I’m happy to share insights and expert guidance, no pressure, no obligations. Simply enter your contact below, and I’ll get back to you.

    By submitting this form, you acknowledge that no agency relationship is created by this submission; such a relationship requires a written agreement (Illinois Real Estate License Act of 2000). The personal information you provide will be used solely to respond to your inquiry and will not be sold or shared with third parties. See Privacy Policy for full details.

    NEWS & INFORMATION

    North Shore Market Sees Rising Competition

    The North Shore continues to see increased demand for luxury homes priced between $2 million and $3 million. Properties that once lingered on the market for six months or more are now selling within 60 days due to height...

    Read More

    Cirrus Penthouse Sale Reflects Downtown Condo Strength

    Downtown Chicago’s luxury condo market remains robust, as evidenced by the recent $4.1 million sale of a penthouse in the Cirrus condo tower. Located along the lakefront, this property offers breathtaking views and pre...

    Read More

    West Town Modern Home Highlights Buyer Preferences

    In Chicago’s West Town neighborhood, a contemporary single-family home listed at $1.5 million exemplifies the evolving tastes of luxury buyers. This five-bedroom, 3.5-bath property features modern amenities, sleek arch...

    Read More
    Office location - Ken JUNGWIRTH