The five highest-priced home sales reported in Chicago, Illinois for the week ending October 25, 2026 came to a combined $14.76 million. Two of them were in the Gold Coast, and the other three were in North Center, Bucktown and Ravenswood.
The group runs from a single-family home built in 1888 to one completed in 2018, and it includes the only condominium on the list, a residence in a Gold Coast hotel tower. Carrie McCormick of @properties Christie’s International Real Estate was the listing agent on three of them.
No. 1 — $4,020,000 · 1434 N Dearborn St, Chicago, Illinois
The oldest home in this group is also the largest. Built in 1888, the limestone single-family home on North Dearborn Street sold for $4,020,000, and it has about 6,815 square feet across three stories on a 3,725-square-foot lot, with five bedrooms and seven bathrooms, five full and two half.
Its interiors keep the period bones, including tall ceilings and original millwork, and set them against a restrained Scandinavian-influenced design. The kitchen and family room share a modern fireplace and a wall of glass that opens to a large terrace at the back. Formal living and dining rooms sit apart from that everyday space, and the home has five fireplaces in all, among them one in the den and one in the primary bedroom.
The primary suite takes the whole top level. Its bath was redone in slate and travertine with hemlock accents, and a soaking tub sits under a skylight. A sauna and a room for yoga or workouts are part of the suite, and a private terrace opens off this floor among the tree canopy. Three more bedrooms and a family room are on the second level, a guest suite is on the lower level, and a private elevator connects the floors. The home also has an attached three-car garage, and the lakefront, parks and the Latin School of Chicago are a short walk away.
The property last sold for $2.6 million in 2012.
Carrie McCormick of @properties Christie’s International Real Estate was the listing agent, and Emily Sachs Wong, also of @properties Christie’s International Real Estate, represented the buyer. It was the first of three listings by McCormick in this week’s Top 5, and @properties Christie’s International Real Estate was the listing brokerage on three of the five sales.
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No. 2 — $3,500,000 · 11 E Walton St Apt 4402, Chicago, Illinois
Lake Michigan is the draw at this residence in the Waldorf Astoria Chicago, which sold for $3,500,000. The unit was built in 2008 and has about 3,436 square feet, with three bedrooms and four bathrooms, three full and one half, plus one garage parking space.
The plan departs from the building’s usual layout. The foyer leads straight into the living room, and the kitchen faces east, so the kitchen and family room both look out to the lake. The kitchen has been upgraded and is fitted with a La Cornue stove. The owner added custom millwork, automated shades and three fireplaces, and an office also has a view of the lake. There are formal living and dining rooms for entertaining, and terraces face both east and west, one for the sunrise and one for the sunset. The primary suite has a double-door entry, a spa-style bath and two walk-in closets.
Owners have the use of the hotel’s services, including a door staff and concierge, a fitness center, an indoor pool, a spa and in-residence dining. The property last sold for $2.89 million in 2010.
Susan Miner and Marina Prodanovic of Premier Relocation, Inc. were the listing agents. Lisa Petrik of Jameson Sotheby’s Intl Realty represented the buyer.
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No. 3 — $2,975,000 · 2107 W Bradley Pl, Chicago, Illinois
With six bedrooms, this custom North Center home on Bradley Place has more than any other in this week’s group. It was built in 2018, sold for $2,975,000, and has about 6,300 square feet across three stories, with six bathrooms, four full and two half, on a 4,464-square-foot lot. The exterior is brick and limestone.
Floor-to-ceiling windows on two exposures bring light into the open main floor. The living room has a gas fireplace with a marble surround and a picture window looking out on Bradley Place, and a study sits just off the dining room. At the center of the floor is an eat-in kitchen with an oversized island and breakfast bar and two sinks. Beside it are a butler’s pantry fitted with a wine fridge and a breakfast room where a banquette is built in. The kitchen opens to a family room with built-ins, a second fireplace and windows on two walls.
The primary suite fills half of the second floor, with a sitting room, two custom walk-in closets and a bath with a steam shower, a soaking tub and heated floors. Three more bedrooms share that level. The front one has a vaulted ceiling and a loft above it that is also reached from the third floor, where a roof deck has a hot tub. The lower level has a recreation room with a movie screen, a gym, a temperature-controlled wine room and two more bedrooms.
A breezeway with heated floors leads to a heated three-car garage, and a deck with a pergola sits over the garage. The property last sold for $2.5 million in 2022.
Carrie McCormick of @properties Christie’s International Real Estate was the listing agent, the agent’s second listing in this Top 5. Jeffrey Lowe of Compass represented the buyer.
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No. 4 — $2,162,500 · 2029 N Hoyne Ave, Chicago, Illinois
Glass, steel and porcelain define this modern Bucktown home on a corner lot on Hoyne Avenue, which sold for $2,162,500. Built in 2015, it is wrapped on three sides in a ventilated Porcelanosa porcelain facade set within a Kawneer curtain wall, and tall glass brings in light from the south and west. Walnut floors run through the interiors and warm up the harder materials.
The home has about 3,400 square feet across three stories on a 2,400-square-foot lot, with four bedrooms and four bathrooms, three full and one half. The main floor moves from the living and dining areas to an open kitchen with quartz counters, a Wolf range and Sub-Zero refrigeration, and on to a family room with a gas fireplace and custom built-ins. The primary suite is upstairs with a travertine bath, and the lower level has radiant heat, a recreation room with a wet bar and a fourth bedroom with its own bath.
The top floor is built for the outdoors. Two NanaWall systems open the den on its east and west sides to a pair of rooftop terraces with a wet bar, a sink and a gas hookup. Another outdoor space, laid with turf and topped with a pergola, sits on the roof of the attached two-car garage. The 606 Trail, Walsh Park, Churchill Park and the Blue Line are all close by.
The property last sold for $417,000 in 2013, before the current home was built.
The home went under contract 16 days after it was listed. Carrie McCormick of @properties Christie’s International Real Estate was the listing agent, which made three listings in this week’s Top 5 for McCormick. Lance Kirshner of Compass represented the buyer.
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No. 5 — $2,100,000 · 2109 W Sunnyside Ave, Chicago, Illinois
Built in 2013, this Ravenswood home on Sunnyside Avenue sold for $2,100,000. It has stone and fiber cement on the outside and about 3,800 square feet inside, with five bedrooms and six bathrooms, four full and two half, on a 3,250-square-foot lot.
Its outdoor spaces get as much attention as the rooms. A covered front porch is heated, with radiant floors and overhead heaters. The backyard has a wood-burning fireplace, and the roof of the detached two-car garage is a deck with a television and room for a dining table.
Inside, the kitchen was renovated with a butcher-block island, marble counters and Wolf and Sub-Zero appliances, and a walk-in butler’s pantry connects it to a family room with a gas fireplace and built-ins. Upstairs, three of the bedrooms have their own baths, including the primary, which has radiant floor heat, a soaking tub, a multi-head shower and a walk-in closet. The finished lower level adds a second family room with a wet bar and a fireplace, a guest suite and a room that can serve as an office or a bedroom. The property last sold for $1.28 million in 2013.
The home went under contract 15 days after it was listed and sold at its full asking price. Holly Futrell of Compass was the listing agent, and Tommy Choi of Keller Williams ONEChicago represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 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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