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Old Town Chicago Luxury Homes for Sale

Old Town Luxury Homes for Sale


Luxury Homes Old Town Chicago

Luxury homes in Old Town, Chicago offer refined living with high-end craftsmanship and timeless design in one of the city’s most historically rich neighborhoods. These residences often feature expansive floor plans, soaring ceilings, and floor-to-ceiling windows that fill the interiors with natural light. Finishes include wide-plank hardwood flooring, natural stone or marble countertops, custom millwork, and designer lighting. Kitchens are equipped with integrated, panel-ready appliances, oversized islands, and bespoke cabinetry. Primary suites include dressing rooms, radiant-heated floors, and spa-level baths with soaking tubs and natural stone finishes.

Many luxury homes also offer private in-home elevators, heated attached garages, smart home systems, and multiple outdoor spaces such as rooftop decks, terraces, or private yards.

Set along tree-lined streets and surrounded by historic architecture, these homes blend modern elegance with classic charm. With close proximity to the lakefront, Lincoln Park, dining, and cultural destinations, Old Town offers upscale city living in a coveted residential setting.

Old Town Luxury Homes for Sale


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Midwest Real Estate Data LLC Logo The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Jameson Sotheby’s are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is 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. Information deemed reliable but not guaranteed. Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Listings courtesy of NEIRBR Northeast Iowa Regional Board of Realtors as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time.

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Listing information last updated on October 23rd, 2025 at 4:09am CDT.