A 1907 house at 320 Melrose Ave in Kenilworth sold for $4.6 million, the highest-priced home sale publicly reported in the Chicago, Illinois metro area for the week ending August 16, 2026.
The week’s five highest reported sales combined for $19.68 million and span Kenilworth, Winnetka, Chicago and Lake Forest, with Winnetka appearing twice on the list. Build years run from 1907 to 2025, taking in two early-1900s houses by named architects, a custom-built Lake Forest estate and a new-construction residence in Lincoln Park.
No. 1 — $4,600,000 · 320 Melrose Ave, Kenilworth, Illinois
A 1907 house at 320 Melrose Ave in East Kenilworth sold for $4,600,000, the highest reported price in the Chicago metro area for the week. The five-bedroom, six-bathroom residence holds a reported 6,754 square feet, and the sale closed on August 12, 2026. The property previously changed hands for $2,229,500 in 2023.
Listing materials identify George Maher as the architect and credit designer Sarah Richardson with a renovation that reworked the second floor into four bedrooms and three baths, added a third-floor suite with a playroom and two offices, and finished an in-law suite above a new heated two-car garage. Original millwork, leaded glass windows and a central staircase came through the work, and an elevator serves every floor.
The kitchen has a quartzite island, Wolf and Sub-Zero appliances and a wall of windows over the terrace and patio, and the dug-out lower level, with nine-foot ceilings, holds a recreation room, fitness room and wine room. A coach house above the garage adds a one-bedroom guest suite with its own kitchen, and Sears School, New Trier High School, the Kenilworth beach and the train are within walking distance.
Jena Radnay of @properties Christie’s International Real Estate was the listing agent. The $4,600,000 closing placed her on the listing side of the highest-priced home sale reported in the Chicago metro area for the week ending August 16, 2026, and No. 1 in RealtyWire’s Chicago Metro Area Top 5. It is Radnay’s second appearance in a RealtyWire Top 5 roundup for the metro. Katie Hackett of @properties Christie’s International Real Estate represented the buyer.
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No. 2 — $4,300,000 · 605 Arbor Vitae Rd, Winnetka, Illinois
A 1915 residence at 605 Arbor Vitae Rd sold for $4,300,000, the second-highest reported price of the week and the first of two Winnetka sales on the list. The seven-bedroom, six-bathroom house occupies an elevated setting in East Winnetka; the transaction closed August 14, 2026, and the property previously changed hands for $2,550,000 in 2018.
Listing materials identify Otis & Clark as the architects and refer to the house as Winnetka’s βCastle on the Hill.β A barrel-vaulted reception gallery opens the interior, and a skylit atrium-style great room faces the grounds through a wall of French doors. The kitchen carries a La Cornue range, Sub-Zero and Miele appliances and radiant heated floors, and a renovated pool and built-in fire pit sit in landscaped grounds a short walk from downtown Winnetka and the Lake Michigan beach. The house has been featured in Luxe Magazine and on the Winnetka Community Housewalk.
Megan Panje-Wilson and Megan Mawicke Bradley of Jameson Sotheby’s International Realty were the listing agents. Their listing went under contract 5 days after the current listing date and closed $450,000 above its final asking price of $3,850,000, ranking No. 2 in RealtyWire’s Chicago Metro Area Top 5 for the week. Carrie McCormick of @properties Christie’s International Real Estate represented the buyer.
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No. 3 — $4,100,000 · 545 W Grant Pl, Chicago, Illinois
A newly built house at 545 W Grant Pl, one of the Residences at Grant Place in east Lincoln Park, sold for $4,100,000. Completed in 2025, it has seven bedrooms, seven bathrooms and a reported 6,300 square feet over four levels above grade. The sale closed on August 10, 2026.
Listing materials identify Merrion Development Group as the builder and JenMarie Design as the interior designer. The house has an elevator, an attached subterranean garage with parking for as many as five cars, high ceilings on every floor and a half-floor primary suite. A 27-foot-wide backyard and a roof deck adjoin direct access to the half-acre private park at Webster Square, with Oz Park, Lincoln Park Zoo, the Peggy Notebaert Museum and Lake Michigan a walk away.
Marc Zale of Compass was the listing agent. The house went under contract the same day the current listing went live and closed at its full asking price, ranking No. 3 in RealtyWire’s Chicago Metro Area Top 5 for the week ending August 16, 2026. Jeffrey Lowe of Compass represented the buyer.
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No. 4 — $3,510,000 · 566 Willow Rd, Winnetka, Illinois
A limestone and stone residence at 566 Willow Rd in East Winnetka, built in 2005, sold for $3,510,000. The six-bedroom, seven-bathroom house carries a reported 6,689 square feet across four levels beneath a slate roof, with a sight line to Lake Michigan from the front. The sale closed August 14, 2026, and the house previously changed hands for $2,585,000 in 2023.
Formal rooms off the reception foyer include a living room with a limestone fireplace and a paneled office with built-in bookcases, while the family room and a remodeled kitchen with a center island and window-wrapped breakfast room face the backyard and a sports court. A primary suite with dual walk-in closets and a spa bath anchors the second floor, and a third-floor suite opens to a private rooftop sun deck.
Carrie Tarzon of @properties Christie’s International Real Estate was the listing agent. The property went under contract 3 days after the current listing date and closed $485,000 above its final asking price of $3,025,000, ranking No. 4 in RealtyWire’s Chicago Metro Area Top 5. The same brokerage held the listing on the week’s top sale in Kenilworth. Kathryn Mangel of @properties Christie’s International Real Estate represented the buyer.
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No. 5 — $3,168,750 · 1150 W Keswick Ln, Lake Forest, Illinois
An all-brick Georgian estate at 1150 W Keswick Ln in Lake Forest completed the week’s top five at $3,168,750. Custom built and finished in 2016, it has five bedrooms, eight bathrooms and a reported 6,554 square feet. The sale closed August 13, 2026. The property previously changed hands for $2,150,000 in 2008, before the current residence was completed in 2016.
A bridal staircase and detailed millwork open the house, and a two-story great room draws light from tall windows facing the backyard. The white kitchen has a large center island, and a first-floor office with built-ins and a first-floor primary suite with a spa bath sit on the same level, with four more bedroom suites, each with an en-suite bath, upstairs. A screened porch overlooks a pool and spa, an outdoor fireplace and lounge areas, and the lower level holds a wine room and exercise room.
Nancy Adelman of Compass was the listing agent. The house went under contract 8 days after the current listing date and closed at $3,168,750, the No. 5 sale in RealtyWire’s Chicago Metro Area Top 5 for the week ending August 16, 2026; Compass also held the listing on the No. 3 sale in Lincoln Park. Thomas Kraley of Thomas Kraley represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 16, 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.
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