For residential real estate, 2025 was the year of the Chicago-area megasale.
Two mansions on the North Shore sold for more than $30 million each, setting new Chicago-area sales records.
The first was a French Renaissance Revival-style mansion at 419 Sheridan Road in Winnetka, which sold in September for $31.3 million, becoming the highest-priced home resale in Chicago-area history. But that record was eclipsed in November when another Winnetka mansion — at 609 Sheridan Road — sold for $34.5 million.
Those two sales were the tip of the spear for a year in which the high-end market saw 10 residential sales for $9.5 million or more.
The reasons why high-end homes are selling for increasing prices have been well-documented, including continued gains in the stock market and wealthy individuals’ general insulation from factors such as mortgage rates.
If there’s one thread that ties together the 10 highest-priced home sales in 2025, it’s Lake Michigan. Fully eight of the 10 highest-priced Chicago-area home sales involved single-family homes with frontage on Lake Michigan, in the communities of Winnetka, Kenilworth and Lake Bluff. A ninth property, in Lake Forest, sits within little more than shouting distance of the lake, while the final property is a Chicago penthouse with lake views.
While it’s a cliche to say that they’re not making any more lakefront land, what’s clear is that buyers are valuing Lake Michigan frontage on the North Shore in ways they never have before. Of 2025’s top 10 sales, six of the eight lakefront properties on the list — including four of the top five — are in Winnetka.
Real estate agent Jena Radnay of @properties Christie’s International Real Estate, who was involved in seven of the top 10 Chicago-area sales in 2025, attributed the growing interest in lakefront homes and their elevated prices to “protected luxury.”
“Protected luxury has never been more at the forefront,” Radnay said. “The Midwest is fortunately an area that doesn’t have catastrophic events happen from a weather perspective, and through the last couple years, people have seen what has happened with fires and flooding in places like Malibu and Texas.”
Radnay also said the North Shore’s great communities, educational institutions, and fine dining opportunities are appealing to buyers.
“Those are the things that attract people to the North Shore. That’s why we get the prices that we do,” she said. “This is like the Aspen of the Midwest — things on the lake just keep increasing in value. It’s a great investment.”
Here’s a look at the Chicago area’s top 10 residential sales in 2025, according to public records.
1. $34.5 million
609 Sheridan Road, Winnetka
This five-bedroom, 16,000-square-foot Georgian-style mansion with 151 feet of beachfront along Lake Michigan sold in November for $34.5 million. Records showed that the sale price included $2 million worth of personal property, which usually refers to furniture. Without the personal property, the recorded property sale price was $32.5 million. The mansion was built in 2016 and designed by architect Bill Fork.
2. $31.25 million
419 Sheridan Road, Winnetka
This seven-bedroom, 13,894-square-foot vintage French Renaissance-style mansion, known as Windsor House, sold in September for $31.25 million. Built in 1928 and designed by architect Ernest Mayo, the 22-room mansion has 223 feet of private beachfront. The sellers said they put between $65 million and $72 million into creating the estate, which included buying the mansion for $9.5 million in 2002 and spending another $4.1 million in 2013 for the property next door. The sellers first listed it for $35 million in 2024.
3. $14.5 million
219 Sheridan Road, Kenilworth
This six-bedroom mansion on the lake sold in October for $14.5 million — a record sale price for Kenilworth. The mansion was constructed by Paul Starrett, who also built the Empire State Building in New York and the Lincoln Memorial in Washington, D.C. The mansion has 115 feet of sandy beach.
4. $12 million
973 Sheridan Road, Winnetka
This seven-bedroom, 9,653-square-foot mansion on the lake in Winnetka sold in June for $12 million — which up to that point had been the year’s highest sale price. The mansion was built in 2020 and designed by architect Paul Konstant, on the site of an earlier, now-demolished mansion that had been built in 1991 for the late philanthropists Robert and Ann Lurie.
5. $11.4 million
765 Sheridan Road, Winnetka
This seven-bedroom, 15,784-square-foot mansion on the lake in Winnetka sold in July for $11.4 million. Built in 2005 by Orren Pickell Builders and once listed for $18 million, the mansion sits on a 1.3-acre parcel and has a Marc Chagall-inspired circular mosaic ceiling. The property has both stairs and an electric tram leading to the beach, along with more than 100 feet of sandy beach.
6. $11.25 million
700 Crabtree Lane, Lake Bluff
This six-bedroom, 9,990-square-foot mansion on fully 27 acres in Lake Bluff sold in December for $11.25 million. Once listed for $22.9 million, the estate has polo fields, equestrian stables with 13 stalls, and no less than 700 feet of private Lake Michigan beach access.
7. $11 million
930 E. Rosemary Road, Lake Forest
In October, a vintage eight-bedroom, 11,787-square-foot ivy-covered red brick Georgian-style mansion on 8.68 acres in Lake Forest — but not on the lake — sold for $11 million. Designed by architect Benjamin Marshall and known as Camp Rosemary, the estate, just southeast of Lake Forest College’s campus, sold to a Wisconsin-based developer who plans to renovate its interior and enhance its grounds. The estate is known for its extensive gardens, which include 21 outdoor garden “rooms.” Its landscaping was designed in the 1920s by noted landscape architect Rose Standish Nichols.
8. $10.125 million
4 E. Elm Street, PH23, Chicago
In March, the full-floor penthouse on the 23rd floor of the building at 4 E. Elm St. on the Gold Coast sold for $10.125 million. The four-bedroom unit’s build-out was designed by architect Paul Konstant — which marks his second appearance on this top 10 list — and the penthouse has 11-foot ceilings, wide-plank hardwood floors with a herringbone inlay, a 60-foot entertaining terrace, and views to the east, south and west. The recorded sale price was $9.78 million, which means that the remaining $341,000 included in the purchase price was personal property like furniture.
9. $9.575 million
381 Sheridan Road, Winnetka
In June, a six-bedroom, 8,086-square-foot mansion on the lake sold for $9.575 million. Built in 2015, the mansion, which has 88 feet of beachfront, actually sold in 2018 for $12 million and then sold again in 2022 for just $7 million. The mansion extends from Sheridan Road to the lakeshore, making it something of a rarity in Winnetka.
10. $9.499 million
139 Sheridan Road, Winnetka
This six-bedroom, 9,723-square-foot mansion on the lake sold in July for slightly less than $9.5 million. Built in 2021, the home, whose southern lot line is the Winnetka-Kenilworth border, is built into the bluff and sits on a 0.75-acre property. It has a boathouse whose zoning is grandfathered by the village.
Bob Goldsborough is a freelance reporter.
