A custom-built house on South Columbia Street in Naperville went under contract 12 days after the current listing date and closed at $3,025,000 on September 18, 2026. The sale led a week of five reported closings totaling $13.13 million across the Chicago, Illinois metro area, covering September 14 through September 20.
Naperville produced both that leading price and the No. 3 closing, on Jackson Avenue, while the other three sales were recorded inside Chicago, in Kenwood, Lake View and Lincoln Park. A 1909 residence in the South Kenwood Historic Landmark District and a 2020 house near the Southport Brown Line stop bracket the group’s build dates. Compass held the listing side on the Naperville leader and on the Lake View sale.
No. 1 — $3,025,000 · 471 S Columbia St, Naperville, Illinois
A custom-built Cape Cod on South Columbia Street, finished in 2013 for the owners who commissioned it, brought $3,025,000 when the sale closed September 18, 2026. The house carries a reported 9,967 square feet, five bedrooms and seven baths across four levels, with a HardiePlank exterior and hand-scraped hickory floors throughout.
The main floor centers on a kitchen with a Viking 60-inch range, Sub-Zero refrigeration, Cambria quartz counters and multiple oversized islands, with a formal dining room, family room, den, two offices and a guest suite with direct pool access alongside it. Rustic wood trussing crosses the vaulted primary suite, which opens to a wood-paneled three-season room with its own fireplace. Three more bedrooms each have a private full bath and heated flooring, and the fifth has a private staircase up to a third-level playroom.
A 3,200-square-foot English basement laid with Chicago brick tile holds a cedar-planked gym, a fireside lounge, a bar with a 36-inch Sub-Zero wine tower and a tiered theater seating 12. Outside, a saltwater pool with a waterfall wall and a jetted whirlpool sits behind a perimeter of mature arborvitae, with a covered porch under a cedar V-groove ceiling, a built-in Viking grill and a bluestone patio around a wood-burning fireplace. A four-car side-load garage keeps the Cape Cod frontage intact, and the property sits in District 203 within walking distance of downtown Naperville and the Riverwalk.
Oriana Van Someren of Compass represented the listing side of the $3,025,000 transaction, which ranked No. 1 in RealtyWire’s Chicago metro area Top 5 for the week ending September 20, 2026. The house went under contract 12 days after the current listing date. The property previously changed hands for $350,000 in 2010, before the current residence was completed in 2013. Emma Matuska of Compass represented the buyer.
See this property in Google Street View →
No. 2 — $2,725,000 · 4933 S Woodlawn Ave, Chicago, Illinois
In the South Kenwood Historic Landmark District, a three-story brick residence at 4933 S Woodlawn Ave sold for $2,725,000 on September 14, 2026. Records date its construction to 1909; listing materials identify George Beaumont as the architect and Chicago industrialist and philanthropist Bernard E. Sunny as the original owner, with a comprehensive Art Deco-era remodeling following in 1937. The house carries a reported 7,500 square feet, seven bedrooms and five baths.
An oval reception hall with a sweeping curved staircase opens onto a living room, formal dining room, kitchen with butler’s pantry and breakfast room overlooking the rear patio and garden. Off the living room is a library finished with leather-clad walls and a concealed bar. The second and third floors each hold three bedrooms and two full baths, with a sun porch, a private terrace and a semi-enclosed reading nook among the individual details.
At the rear of the lot, a recently renovated two-story coach house carries a three-car garage on its main level and a one-bedroom apartment above it. The University of Chicago campus and the Lab Schools are nearby, with Lake Shore Drive, Metra stations and downtown bus routes close at hand.
Robert Sullivan and Susan O’Connor of Berkshire Hathaway HomeServices Chicago were the listing agents. The sale placed Sullivan and O’Connor at the listing side of the No. 2 transaction in RealtyWire’s Chicago metro area Top 5 for the week, and the house previously changed hands for $710,000 in 1998. Norene Chip of Jameson Sotheby’s Intl Realty represented the buyer.
See this property in Google Street View →
No. 3 — $2,550,000 · 907 Jackson Ave, Naperville, Illinois
A 2017 house on Jackson Avenue went under contract the same day the current listing went live and closed at its full asking price, a $2,550,000 transaction recorded September 15, 2026. Built by Lenahan Builders, it holds five bedrooms and six baths across a reported 3,980 square feet on an 80-by-165-foot homesite at the end of a private cul-de-sac.
The open main floor runs to high ceilings, hardwood flooring and extensive millwork, with a white kitchen at its center fitted with Thermador appliances, quartz counters and an oversized island that opens to the family room. The primary suite is on the first floor, with two walk-in closets and a bath holding dual vanities, a soaking tub and an oversized shower, and a first-floor office sits nearby.
A 15-by-15-foot three-season room has a fireplace and motorized retractable screens that close it in on cool evenings, and the walkout lower level opens directly to a fenced, landscaped backyard. A vehicle lift is fitted in the three-car garage. Downtown Naperville, the Riverwalk, District 203 schools and the Metra station are all within walking distance.
The same-day contract and full-price close put Bridget Salela and Walter Burrell of Coldwell Banker Realty at the listing side of the No. 3 reported sale in RealtyWire’s Chicago metro area Top 5 for the week. The property previously changed hands for $1,364,000 in 2018.
See this property in Google Street View →
No. 4 — $2,550,000 · 1219 W Roscoe St, Chicago, Illinois
Thady Construction completed the six-bedroom house at 1219 W Roscoe St in 2020, on a tree-lined block in the Southport Corridor section of Lake View. It changed hands September 17, 2026 for $2,550,000 and carries a reported 4,200 square feet and six baths.
White oak floors run through the main level, where two wood-burning fireplaces with gas starters anchor the public rooms and the kitchen holds maple cabinetry, quartz counters, an oversized island, a built-in banquette and a butler’s pantry set with brass grill inserts. A mudroom off the family room is laid with heated Unilock pavers, keeping the path between house and garage clear in winter.
Four bedrooms, three full baths and a laundry room occupy the upper level, where the primary suite rises to cathedral ceilings with dual walk-in closets and a marble bath. Radiant heated floors warm a lower level holding two more bedrooms and a recreation room with a wet bar. The garage roof deck is built from Azek PVC under a privacy pergola, and the detached two-car heated garage carries 220-volt service for EV charging and snowmelt paver access. The Southport Brown Line stop, Southport Corridor restaurants and Wrigley Field are all close by, and the house is in the Hamilton Elementary district.
The transaction ranked No. 4 in RealtyWire’s Chicago metro area Top 5 for the week and was listed by Tony Mattar of Compass. The house previously changed hands for $1,850,000 in 2020. Melissa Siegal of @properties Christie’s International Real Estate represented the buyer.
See this property in Google Street View →
No. 5 — $2,275,000 · 1032 W Montana St, Chicago, Illinois
Two blocks from the L in Lincoln Park, a five-bedroom house on West Montana Street closed on September 15, 2026 for $2,275,000, $75,000 above its final asking price of $2,200,000. Completed in 1998, it carries a reported 4,500 square feet and four baths.
The first floor sets the living and dining rooms around a marble-clad, gas-started wood-burning fireplace, one of three wood-burning fireplaces in the house. The kitchen is finished with white cabinets, quartzite counters and a matching backsplash, with room for a table seating six, and a step down leads to a family room with the second fireplace and built-ins. Light oak floors run throughout.
Three bedrooms and two baths sit on the second floor, where the primary bedroom has its own fireplace and a spa-style bath with a whirlpool tub and a double-bowl sink. The third level is arranged as a combined office and gym and opens to a large private Trex deck, and two more bedrooms and a bath occupy the lower level beside a family space with room for a pool table. A private patio, a second deck and a two-car garage with an EV charger fill the rear of the lot; DePaul University is a neighbor and the house is in the Oscar Mayer school district.
The house went under contract 5 days after the current listing date and closed above its final asking price, the No. 5 reported sale in RealtyWire’s Chicago metro area Top 5 for the week, with Eileen Brennan and Karen Peterson of Baird & Warner as the listing agents. The property previously changed hands for $1,440,000 in 2004. Heather Seidelman of @properties Christie’s International Real Estate represented the buyer.
See this property in Google Street View →
RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, September 20, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
Were you involved in one of these transactions? Contact RealtyWire to verify or correct your professional credit or submit information for a future edition.
See full market data on our Chicago, Illinois market page.
