Brick and limestone under a slate roof, the six-bedroom house at 794 Greenwood Ave in Glencoe was completed in 2026 with a three-stop elevator, a walnut library and a refrigerated wine cellar on its lower level, a short walk from the village’s downtown, its beach, its schools and the train.
Together the five highest-priced home sales reported in the Chicago, Illinois metro area for the week ending September 27, 2026 account for $18.62 million. They span Glencoe, Evanston, Hinsdale, the Midwest Club community in Oak Brook and Northbrook, and they range from a 1904 house on the Lake Michigan shoreline to new construction finished in 2025 and 2026. @properties Christie’s International Real Estate held the listing side in Glencoe, Evanston, Hinsdale and Northbrook, and Baird & Warner in Oak Brook.
No. 1 — $5,225,000 · 794 Greenwood Ave, Glencoe, Illinois
A newly finished house on Greenwood Avenue in Glencoe sold for $5,225,000 on September 23, 2026, the highest-priced home sale publicly reported in the Chicago metro area for the week. The transitional-style residence was completed in 2026 and holds six bedrooms and eight baths across a reported 9,000 square feet. The property previously changed hands for $1,625,000 in 2024, before the current residence was completed in 2026.
Brick and limestone form the exterior beneath a slate roof. Three fireplaces are set through the house, the Neff kitchen is fitted with Sub-Zero refrigerators and freezers, a Wolf range and a drawer-style microwave, and the walnut library carries a built-in desk and filing cabinets. A three-stop elevator serves the floors.
The finished lower level holds an entertainment room with a fireplace, a refrigerated wine cellar, a full-size wet bar and a media room with 4K video and surround sound, along with a sport court. An outdoor pool and Jacuzzi sit in the grassy rear yard, and the house carries a security system, a back-up generator and prewiring for smart-home controls.
Milena Birov and Leo Birov of @properties Christie’s International Real Estate were the listing agents. The $5,225,000 closing placed the pair on the listing side of the highest-priced home sale reported in the Chicago metro area for the week ending September 27, 2026, a transaction that ranked No. 1 in RealtyWire’s Chicago Metro Area Top 5.
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No. 2 — $3,700,000 · 90 Kedzie St, Evanston, Illinois
Michael Thomas, CRS, Green of @properties Christie’s International Real Estate was the listing agent. The listing went under contract 26 days after the current listing date, and the $3.7 million sale ranked No. 2 in RealtyWire’s weekly Chicago Metro Area Top 5. Kenton Girard of Kenton Realty Group represented the buyer.
A lakefront house at 90 Kedzie St in Evanston, built in 1904, changed hands for $3.7 million, with the sale recorded on September 22, 2026. The five-bedroom, six-bath residence measures a reported 5,865 square feet on a double lot of more than half an acre, with over 150 feet of private Lake Michigan shoreline, a boat dock and a boat lift.
Picture windows face the water from every first-floor room, where the living room, dining area, family room and breakfast room open into one another. The kitchen holds an oversized island with quartzite waterfall counters, Sub-Zero, Wolf and Miele appliances and a walk-in pantry, and the primary suite adds a fireplace, a dressing room and a new bath with a 280-degree lake panorama.
A fifth bedroom and a recreation room with lake views fill the third floor, the finished lower level adds an exercise room, and a deck and a second patio at the private dock face the water. Southeast Evanston places the house steps from Main Street’s shops and from Metra and CTA stations.
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No. 3 — $3,400,000 · 104 S Monroe St, Hinsdale, Illinois
New construction at 104 S Monroe St in Hinsdale, finished in 2025, closed on September 21, 2026 for $3.4 million. The house offers seven bedrooms and eight baths across a reported 7,500 square feet, and the property previously changed hands for $516,000 in 2022, before the current residence was completed in 2025.
The Belgian farmhouse-inspired design carries 12-foot ceilings, chevron white oak floors and a double-sided limestone fireplace. Its open main floor centers on a kitchen with a 10-foot waterfall quartzite island and a separate scullery, beside a great room lined with floor-to-ceiling windows, and the primary suite has cathedral ceilings, a fireplace and a bath with heated floors and a wet room.
Every second-floor bedroom is en suite, a third-floor bedroom has its own bath, and the lower level holds a media room, a recreation space with a custom wet bar, a seventh bedroom that can serve as a fitness room, and a full bath. Four patios wrap the exterior, one a covered terrace with a stone gas fireplace, and downtown Hinsdale and the Monroe Elementary, Hinsdale Middle and Hinsdale Central schools are within walking distance.
@properties Christie’s International Real Estate represented the listing side of the $3.4 million transaction, which ranked No. 3 in RealtyWire’s Chicago Metro Area Top 5 for the week ending September 27, 2026. The individual listing agent could not be verified.
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No. 4 — $3,312,500 · 1901 Midwest Club Pkwy, Oak Brook, Illinois
Inside Midwest Club, the gate-guarded Oak Brook community staffed around the clock, a 1987 house facing the main pond sold for $3,312,500. The transaction was completed on September 25, 2026. The two-story residence measures a reported 9,862 square feet with six bedrooms, nine baths, seven fireplaces and a four-car garage, and it previously changed hands for $3,250,000 in 2005.
Two-story ceilings rise over the main rooms, separate formal living and dining rooms sit off the hall, and a hardwood-paneled study has its own fireplace, built-ins and private bathroom. The kitchen carries extensive custom cabinetry, hardwood floors and a center island, with a sun room and a guest bedroom with fireplace and bath just off it.
Four second-floor bedrooms each have private baths, and the primary suite runs across two rooms, one a sitting area with a water view and fireplace. According to the listing, the lower level holds a bar room, a whirlpool, a sauna, television and game areas and a bowling lane, and an in-ground pool and hot tub sit outside.
Robert Briant of Baird & Warner represented the listing side of the $3,312,500 transaction, which ranked No. 4 in RealtyWire’s Chicago Metro Area Top 5 sales for the week ending September 27, 2026. The buyer was represented by Katherine Karvelas of @properties Christie’s International Real Estate.
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No. 5 — $2,980,000 · 2 Bridlewood Rd, Northbrook, Illinois
On more than an acre on a quiet Northbrook street, a custom-built contemporary house of limestone and stucco sold for $2.98 million, its closing dated September 25, 2026. The 2006 residence at 2 Bridlewood Rd holds five bedrooms and ten baths within a reported 6,901 square feet, and the property previously changed hands for $1,300,000 in 2005, before the current residence was completed in 2006.
Wood and glass double doors open to a foyer and a great room with volume ceilings, built-ins, a stone-clad fireplace and French doors to the pool and patio. The kitchen combines custom wood slab cabinetry, granite counters and a large island with a prep sink, alongside a formal dining room with a coffered ceiling and a butler’s pantry.
The first-floor primary wing, past an office with crown moldings and built-ins, has a bedroom with a sitting area and fireplace, two baths with heated stone floors and two skylit walk-in closets. Three bedrooms occupy the second floor, one en suite and two sharing a Jack-and-Jill bath, and the radiant heated lower level adds a wine cellar, a game room, an exercise room, a steam shower and a fifth bedroom with private bath. The fenced, landscaped yard holds a cedar pergola, a limestone patio, a pool and spa and an outdoor kitchen.
Beth Wexler and Liz Salinas, Sres of @properties Christie’s International Real Estate were the listing agents. Their $2.98 million Northbrook closing ranked No. 5 in RealtyWire’s Chicago Metro Area Top 5 for the week ending September 27, 2026. Vu Trieu of HomeSmart Connect LLC represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, September 27, 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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