The large seven-bedroom, nine-bathroom home at 35 Indian Hill Road in Winnetka, Illinois, could be ideal for empty nesters looking to upsize.
Upsizing, rather than downsizing, is a seemingly contradictory trend that co-listing agents Nancy Nugent and Linda Levin of Jameson Sotheby’s International Realty say is on the rise.
“Instead of going to a resort location, they’re coming back to where they raised their kids and providing a central homestead so to speak,” said Nugent. “I’ve had three sales in the past 18 months where that was the case.”
It’s the route that the seller of 35 Indian Hill Road took herself, drawn in by the property’s 9,744 square feet and amenities, according to the agents. Rather than purchase a condominium in a beach town as many empty nesters tend to, the seller purchased this home, which includes a pool, pond, dock and large yard and is next door to the Indian Hill Club’s golf course. The agents say it’s one of the largest lots in Winnetka at 2.3 acres.

“She had a place where everyone can gather,” Nugent said of the seller.
The home is listed at $4.95 million, less than the $5.1 million the seller purchased it for in 2023 from the great-grandson of Motorola founder Paul Gavin.
The seller invested more than a million dollars worth of renovations between the infrastructure and outdoor landscaping, including stonework, since the purchase. She also converted the first-floor great room into a primary bedroom.
The agents say the “excellent value” price is due to the seller needing to relocate quickly for work.

The neighboring homes last sold between 2010 and 2019 for between $2.7 million and $4.25 million, according to Homes.com data. Ten homes priced above $5 million have sold in Winnetka in the past year, with two sold in January. The median home price of a single-family home in the Chicago suburb is $1,797,500, according to Homes.com.
Previous owners remodeled extensively between 2017 and 2021. The home features a four-car garage, three floors, a fountain, two laundry rooms, a bar, a walk-in pantry, a sunroom and an elevator.
According to the agents, Indian Hill Road is an “iconic” street in suburban Winnetka. The road features other English-style homes built in the 1920s, including this 1927 property.
“It is a very coveted street,” said Nugent. “There are five homes on the pond and our listing has the most land on the pond.”