The Chicago suburb of Winnetka may look oddly familiar, even if you’ve never been there before. 

The suburb pops up in “Ferris Bueller’s Day Off” and has the home featured in “Home Alone.” If you happened to notice the prime real estate in those classics, it likely comes as no surprise that Winnetka is one of the more expensive suburbs in Chicagoland. The “Home Alone” house actually sold in 2012 for a total of $1.585 million, and that figure is hardly an outlier in this northern suburb.

If you’re seeking to settle down in the northern suburbs, take a look at what Winnetka has to offer. 

Upscale Homes

In 2018, Chicagoland had strong luxury home sales, and Winnetka was high on the list of places with multimillion-dollar home sales. Two homes on Sheridan Road, which runs right alongside Lake Michigan, sold for $12 million each. One home was 12,500 square feet and the other was 5,500 square feet, according to the report. A third home, also among the priciest sales of 2018, on Sheridan Road sold for $10 million, according to Crain’s. 

Large, luxury homes are common in Winnetka, but not all price tags sore into the millions of dollars. For example, Indian Hill has a median sale price in the high $800s, according to Neighborhoods.com data. 

Although single-family homes are the predominate style in the suburb, Winnetka also has attached homes. Oakhill, a residential building dating back to the 1980s, has a median sale price in the low $400s. Winnetka Mews, another multi-unit building, has a median sale price in the mid $400s.

New Development

New construction in Winnetka is fairly common. Older homes are often torn down in favor of larger, more upscale development. 

Developers are busy working on a plan to create a new luxury residential building on the corner of Elm Street and Lincoln Avenue in downtown Winnetka. One Winnetka, which received final approval last year, will feature luxury condos, townhomes, and apartments, according to Crain’s. The project will also include shops and restaurants. 

Buyers have already snagged six of the building’s 21 for-sale units, according to Crain’s. The building is primarily targeted at homeowners who want to downsize. "We believe One Winnetka is part of a bigger nationwide trend for affluent, aging baby boomers," developer David Trandel told Crain’s.

Lakefront Vibes

Winnetka can demand such high prices in part because of its desirable lakefront location. The entire eastern edge of the community runs along Lake Michigan. While a good chunk of that real estate is occupied by luxurious homes, all residents can enjoy the lake. 

The suburb has three park district beaches: Tower Road Beach, Maple Street Beach, and Elder Lane Beach. All three beaches are open for swimming during the summer. Tower Road Beach also has a playground and volleyball courts, while Elder Lane Beach has a boat launch.

Schools

The suburb’s younger school children attend elementary school and middle school in Winnetka Public Schools System District 36. Winnetka is known for its progressive approach to education. Carleton Washburne, appointed superintendent of Winnetka’s public schools in 1919, initiated an educational style now known as the “Winnetka Plan,” according to the Winnetka Historical Society. His focus on individualized learning continues to influence progressive education in the community.

District 36 includes Carleton W Washburne School, Crow Island Elementary School, Greeley Elementary School, Hubbard Woods Elementary School, and The Skokie School.

Winnetka is often a top choice for families with children because of New Trier Township High School, which has a 10 out of 10 rating on GreatSchools.

Getting Around

Winnetka is a little over 20 miles north of Chicago and conveniently offers multiple modes of transportation. Drivers can easily head west from central Winnetka and hit 1-94, which leads directly to the city.

The suburb is also served by the Metra’s Union Pacific/North Line. The train runs parallel to Green Bay Road and has three stations within Winnetka: Hubbard Woods, Winnetka, and Indian Hill. The train will typically deliver commuters to Ogilvie Station in the West Loop within about 40 minutes. 

As a suburb, driving is the easiest way to get around town within Winnetka. But, the community is served by a network of Pace buses, and the downtown area offers walkable shopping, eating, and entertainment options. 

Things to Do

Beyond the lakeshore, Winnetka has a wealth of entertainment options. The suburb has boutiques for those who love to shop. Look for secondhand treasure at Winnetka Thrift Shop, or find something designer at the Neapolitan Collection.

Winnetka also has a varied spread of restaurants. More casual diners will delight in the Original Green Bay Café (classic breakfast and lunch) and Fred’s Garage (American classics served in a rehabbed service station). For an indulgent night out, Restaurant Michael serves French dishes on a prix fixe menu.

This northern suburb has its fair share of greenspace to lure residents outdoors. Sports enthusiasts can golf the 18-hole course at Winnetka Golf Club, which opens each year in the early spring. The golf club also has a driving range open year-round.

The paved, 2.24-mile Green Bay Trail runs along the Metra train line. This space offers a place for people to walk, jog, stroll with their dogs.

Though the Skokie Lagoons bear the name of Winnetka’s neighbor, the lagoons serve as a major attraction for both suburbs. People can canoe, kayak, and fish the extensive water system. Plus, Winnetka Village President Chris Rintz is championing the addition of a new boathouse that would serve as the “gateway to Winnetka.”