Five of the highest-priced publicly reported home sales identified in the Chicago, Illinois metro area totaled $20.9 million for the calendar week ending Sunday, August 2, 2026 — an average of $4.18 million per transaction. The Chicago–Naperville–Elgin metro area includes Cook County and the surrounding collar counties.
The week’s top tier tells a story of vintage housing stock and repeat players. Two of the five properties date to the 1880s and two stand in Lincoln Park, while construction years span 1886 to 2012. One sale closed 14.1 percent over asking after just five days on the market — the week’s only bidding-war result — while the others closed between 2.6 and 14 percent below ask, and one lakefront estate sold without ever carrying a public asking price. Jameson Sotheby’s International Realty held the listing side of two transactions and the buyer’s side of a third, and Dawn McKenna of Coldwell Banker Realty appears twice — as listing agent on the week’s No. 1 sale and as buyer’s agent on its over-ask No. 3. Geographically, the five sales span Lincoln Park, Old Town, Winnetka’s North Shore and a Barrington Hills lakefront.
No. 1 — $5,600,000 · 1703 N Dayton St, Chicago, Illinois
The week’s highest-priced real estate transaction in the Chicago metro area closed July 31 at a publicly reported $5.6 million: a 2012-built Lincoln Park residence on an extra-wide 36-by-125-foot lot on North Dayton Street. The home was designed by architecture firm Booth Hansen, developed by LG Development and finished by interior designer Kara Mann. Across approximately 8,200 square feet, it offers six bedrooms, six full and two half bathrooms, formal living and dining rooms, an oversized chef’s kitchen and family room, a full-floor primary suite with a spa-inspired bath, a sun-filled top-level solarium and the rarity of a three-car attached heated garage.
The sale works out to about $683 per square foot. The marketing arc was brisk for the price point: listed June 17 at $5.75 million, under contract within sixteen days and closed July 31 at 2.6 percent below asking — 44 days from list to close. Public records show the home last traded for $4.275 million in October 2012, when it was newly built; this sale marks a 31 percent gain over that figure. The 2024 property tax bill was $91,004.
Dawn McKenna of Coldwell Banker Realty was the listing agent; Rachel Krueger of Jameson Sotheby’s International Realty represented the buyer.
See this property in Google Street View →
No. 2 — $4,300,000 · 936 Sunset Rd, Winnetka, Illinois
The runner-up closed July 27 at a publicly reported $4.3 million on Winnetka’s North Shore: a 1956 ranch on a 1.29-acre parcel on Sunset Road, sold with a Village-approved, subdivided 0.67-acre buildable lot included in the transaction. The single-level home features a first-floor primary suite, a circular drive, copper gutters, custom cabinetry and a new composite cedar-shake roof, with the included lot giving the buyer the option to expand the estate or build and sell a second residence.
At roughly $1,034 per square foot, this is the highest price per square foot in the report — a figure that reflects the land value as much as the house. Listed May 28 at $4,999,900 and under contract within fourteen days, the property closed 14 percent below its asking price. Public records show it last sold in May 2006 for $2.5 million.
Jena Radnay of @properties Christie’s International Real Estate was the listing agent; Joanne Hudson of Compass represented the buyer.
See this property in Google Street View →
No. 3 — $3,764,000 · 2514 N Burling St, Chicago, Illinois
The most competitive sale of the week was No. 3: an 1888 Lincoln Park home on Burling Street that closed July 31 at a publicly reported $3,764,000 — 14.1 percent above its asking price, the only over-ask closing in this report. Behind a carefully preserved Victorian facade, the residence was gut-renovated to a design by architect Seth Romig and built by GGC, blending Brooklyn-brownstone character with new construction: high ceilings, restrained millwork, Loewen windows, a front parlor with an oversized bay and a chef’s kitchen by Peter Harris of O’Brien Harris.
The bidding moved fast: listed May 13 at $3,299,000, the home went under contract in five days and closed $465,000 over ask. Public records show the property sold for $1.45 million in February 2015, before its transformation.
Linda Levin of Jameson Sotheby’s International Realty was the listing agent; the buyer was represented by Dawn McKenna of Coldwell Banker Realty — the same agent who listed this week’s No. 1 sale on Dayton Street.
See this property in Google Street View →
No. 4 — $3,650,000 · 1352 N La Salle Dr, Chicago, Illinois
No. 4 is an 1886 Old Town mansion on North La Salle Drive that closed July 30 at a publicly reported $3.65 million. Set on an oversized 33-by-149-foot parcel, the home was restored and reimagined in 2016 and refreshed in 2024 by Brianne Bishop Design. The roughly 9,200 square feet of living space — a figure that includes attached guest and in-law residences — carries 12-foot ceilings, intricate original millwork, a four-stop elevator, a full-floor primary retreat, whole-house technology and a five-car brick garage.
At about $397 per square foot, it is the value play of the five. The path to closing took two attempts: an earlier listing went contingent at $3.95 million in mid-May before coming off the market, and the property relisted May 22 at $3.9 million, went pending July 17 and closed 6.4 percent below the final ask.
Julie Harron of Jameson Sotheby’s International Realty was the listing agent; Meg Wood of Compass represented the buyer.
See this property in Google Street View →
No. 5 — $3,600,000 · 55 Otis Rd, Barrington Hills, Illinois
The list closes 35 miles northwest of the Loop, where a gated lakefront estate on Hawley Lake in Barrington Hills sold July 28 for a publicly reported $3.6 million. Built in 2008 on 6.7 acres with two separate gated entrances, the five-bedroom residence offers water views from nearly every room, a main-floor primary suite and an expansive walkout lower level opening toward the lake.
This was the quietest transaction of the five: the listing was recorded as sold during MLS processing, meaning it never carried a public asking price to measure against. The sale equals about $646 per square foot, and public records show the property last traded in November 2007 for $1.65 million — this closing more than doubles that figure. The 2024 property tax bill was $27,081.
Charles Evans of Coldwell Banker Realty was the listing agent; Dean Tubekis, also of Coldwell Banker Realty, represented the buyer — the report’s only transaction handled entirely within one brokerage.
See this property in Google Street View →
RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 2, 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.
