The five highest-priced home sales reported in North Shore & North Suburbs, Illinois for the week ending October 25, 2026 came to a combined $12.07 million. Each one was a single-family home, and each was in a different town: Highland Park, Winnetka, Glencoe, Northbrook and Northfield.
Four of the five were in Cook County and one, the top sale, was in Lake County. The group spans nearly eight decades of building, from a 1920s home to one finished at the start of this century, and it runs from homes of seven bedrooms to three.
No. 1 — $4,375,000 · 1502 Sheridan Rd, Highland Park, Illinois
An English-style home on Sheridan Road in Highland Park, built in 1923 and since rebuilt and renovated, sold for $4,375,000, the highest price of the week. It is the oldest home among the five and also the largest, with 8,170 square feet, seven bedrooms and nine bathrooms, seven full and two half, on three stories and a 0.48-acre lot. Its exterior is brick and fiber cement.
The plan is built for a large household and frequent guests. An in-law or guest suite sits on the main level, and the third level has a loft or den for entertaining along with another suite for teenagers or visitors. On the second level, a generous playroom and recreation room rises under vaulted ceilings, and the primary bedroom has vaulted ceilings of its own. Its bath has a large steam shower and two separate water closets. Every bathroom in the home has heated floors. Beamed ceilings, special millwork, built-in bookcases and hardwood floors run through the interior, and the home also has an indoor pool and a wet bar.
The full finished basement has a recreation area, radiant heat and plenty of storage. Outside there is a partially covered patio and a fire pit, and the circular driveway and the attached garage are both heated. From the home, Millard beach, the Metra, the library and downtown Highland Park are a short walk away. The property last sold for $940,000 in 2024.
Kasia Kusznerko of Baird & Warner was the listing agent for the week’s top sale, and Ben Lalez of Compass represented the buyer.
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No. 2 — $2,800,000 · 64 Locust Rd, Winnetka, Illinois
Of the five sales, 64 Locust Road in Winnetka had the most land: one acre on a quiet lane, with towering mature trees and long-established landscaping. The home is a red brick Georgian built by Hemphill in 1965, and a gravel courtyard and a columned bluestone entrance lead into a travertine foyer of gallery proportions. It sold for $2,800,000.
Most of the living happens on one level. The primary suite and two more bedrooms are on the first floor; the primary has a large dressing room, a bath with a separate tub and shower, and doors that open directly to a bluestone patio. Upstairs, a self-contained suite has its own sitting area, bedroom, full bath and cedar closet. In all, the home has four bedrooms, five bathrooms, three full and two half, and 7,500 square feet on two stories.
There are three fireplaces. One is in a step-down living room, another in a paneled family room with bamboo floors, a wet bar and built-in bookcases that reach the ceiling, and the third in the kitchen, which also has an island, a breakfast area and a butler’s pantry. The dining room has a parquet floor. A sunroom with a slate floor and windows on three walls looks out over the grounds and has a built-in planter. Outside, a walled bluestone patio extends the living space, a brick shed handles garden and seasonal storage, and the attached three-car garage has an extra half bay.
The home went under contract five days after it was listed and sold at its full asking price. Monica Childs of @properties Christie’s International Real Estate was the listing agent, and Mary Grant of the same firm represented the buyer. It was one of two homes in this Top 5 listed by @properties Christie’s International Real Estate, which also had the No. 3 sale.
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No. 3 — $2,145,000 · 1035 Meadow Rd, Glencoe, Illinois
The setting comes first at 1035 Meadow Road, which sits on a third of an acre in the Ravine Bluffs neighborhood of East Glencoe. The brick and stucco home, built in 1997, sold for $2,145,000. It has six bedrooms, five bathrooms and 5,240 square feet over three stories, plus a two-car attached garage and a paver driveway.
The landscaped yard has a broad bluestone patio set up for cooking and gathering in every season, with a built-in Subzero refrigerator, a six-burner gas grill, a limestone fire pit with a gas starter and built-in LED lighting.
Inside, hardwood floors cover the main level. The living room has a fireplace and custom built-ins, and the kitchen, with granite counters and custom cabinets, opens to the family room, which has the second fireplace. A wall of windows brings in the morning light, and there is a breakfast room as well as a separate dining room. A main-level office that can serve as a bedroom has a full bath nearby. The second floor has four bedrooms, among them a primary suite with a walk-in closet, an adjoining room that could be a nursery or office, and a bath with a jetted tub, a walk-in shower and two sinks. The third floor adds room for play or study, and the partly finished lower level has a recreation room with built-in cabinetry, a bedroom or gym and another full bath.
Glencoe and Braeside Metra stations and the Green Bay Trail are close by, and The Botanic Garden, Ravinia and Glencoe Beach are a few minutes away. The property last sold for $1.275 million in 2001.
Kimberly Ann Hoegler of @properties Christie’s International Real Estate was the listing agent, giving the firm its second listing in this Top 5. Scott Ottenheimer of Compass represented the buyer.
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No. 4 — $1,400,000 · 2341 Catherine St, Northbrook, Illinois
Downtown Northbrook, local schools and the train are all a short walk from 2341 Catherine Street, a brick traditional home on a landscaped corner lot of 0.26 acres in the Highlands neighborhood. Built in 2002, it is the newest of the five homes. The property last sold for $1.175 million in 2013, and this time it sold for $1,400,000.
The home has five bedrooms, five bathrooms, four full and one half, and 4,910 square feet on two stories, with hardwood floors and volume ceilings. Two of the bedrooms are primary suites, and two others share a bath that connects them. A large kitchen is open to the family room, which has a gas fireplace and sliding doors to the patio. The first floor also has a den, a living room and a dining room. Downstairs, the finished basement adds a bedroom, a full bath, a recreation room, a playroom and the home’s second fireplace. There is a dog run outside and a heated three-car attached garage.
The home went under contract 13 days after it was listed and sold for $105,000 above its asking price of $1.295 million. Kim Schnoor, ABR,SFR of Re/Max Advantage was the listing agent, and Anne Hardy of Berkshire Hathaway-Chicago represented the buyer.
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No. 5 — $1,350,000 · 22 Regent Wood Rd, Northfield, Illinois
At the back of a cul-de-sac in the Courts Of Regent Woods, 22 Regent Wood Road backs to woods and looks out on a pond. The brick Georgian home, built in 1989, sold for $1,350,000 at its full asking price, 13 days after it was listed.
Its most unusual room is a sunroom with a glass roof and slate tile floor, where windows on nearly every side look into mature trees and, past them, toward the pond and its lily pads. The sunroom opens off the living room, which has vaulted ceilings, a crystal chandelier and a fireplace set between arched doorways topped with transoms. Black and white checkerboard tile runs through the space on the other side. The kitchen pairs glossy white cabinets with a black granite island and counters and has a built-in double wall oven, with a window over the sink facing the trees.
The home has three bedrooms, five bathrooms, four full and one half, and 3,574 square feet on two stories, on a lot of 5,619 square feet. The primary suite is on the first floor, with a walk-in closet and its own bath, and an office off the foyer has a bay window and a full wall of cherry built-ins. Upstairs, a loft-style hallway overlooks the floor below and passes Dutch doors on the way to two bedrooms, each with a full bath and a walk-in closet. The finished basement has a large recreation room, an exercise room, a second office, a full wet bar, two storage rooms and a full bath with a steam shower. The home has a brick driveway and a heated three-car attached garage. Schools, shopping, dining and Metra service into the city are all within easy reach of Northfield. The property last sold for $1.05 million in 2000.
Justin Greenberg of Jameson Sotheby’s International Realty was the listing agent, and Anne DuBray of Coldwell Banker Realty 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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