The name Winnetka roughly translates to "beautiful land" in the Potawatomi tribe's language. This North Shore village bordering Lake Michigan has the benefit of beaches, parks and the surrounding Forest Preserves of Cook County. It's only about 15 miles to downtown Chicago, with access via multiple Metra train stations. "The area has always been the draw for those that work in the Loop," says Daniel O'Donoghue, a real estate broker with Compass.
O'Donoghue grew up here in Winnetka, and his grandparents lived in the neighboring village of Northfield, which shares some similarities and services with Winnetka. He's served the communities throughout his 20-year career in real estate.
The population is about 12,700, yet Winnetka, once farmland, maintains its small-town character, with community and school-based activities and a focus on local businesses. According to the CAP Index, Winnetka receives a crime score of 1 out of 10, less than the U.S. average score of 4.
Winnetka is named after the Native American phrase meaning “beautiful land.”
Centennial Park in Winnetka has a perfect view of Lake Michigan.
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Multimillion-dollar luxury, Cape Cods and condos
Since development sprang up from the lake, there are a greater number of older homes here than inland. Included are early 1900s to 1920s farmhouses, bungalows and Colonial Revival and Tudor Revival houses. Some are sizable, 3,000 to 6,000 square feet, with prices above $1.5 million. In addition to vintage properties, the multimillion-dollar price range includes newer but equally stylish and spacious homes built from the late 1990s until the present.
Generally, the closer to the waterfront, the higher the prices. Among the luxe properties are French-style chateaus and English-inspired manors. In 2023, a lakeside Spanish-style villa with five bedrooms and over 6,000 square feet on a lot of over two acres sold for more than $12 million. And that wasn't the only sale at that price.
A variety of homes built in the second half of the 20th century are more typical of suburbia, as Cape Cods, ranch-style houses and condominium buildings were set in place. A condo under 1,000 square feet might cost under $250,000, and three- to four-bedroom homes of 1,600 to 2,500 square feet go from about $750,000 to over $1 million. O'Donoghue says homeowners invest in remodels and renovations. "There's been a lot of redevelopment over the past several years."
Several streets like Oak, Cherry, Birch, Chestnut and Linden might appeal to families in particular. "A lot of folks in Winnetka like living on the tree streets because they are more walkable and close to schools," O'Donoghue says.
Winnetka's Cape Cod homes have attached garages with driveways for comfortable parking.
The Indian Hill neighborhood of Winnetka is full of large, beautiful homes with varying styles.
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Lloyd Beach, the Green Bay Trail and more
Water access is the main feature on the village's east side, with a handful of beaches just minutes from home. Lloyd Beach has a boat launch and paddleboard rentals. The Winnetka Waterfront 2030 included landscape restoration and a new breakwater system at the beach in 2020 and 2021. Season pass holders have daily access to the beaches from late May until early September.
Other outdoor enjoyment is found in the community parks and nearby nature preserves, like Erickson Woods, with a 4-mile trail linking the Skokie River. O'Donoghue says locals visit for fishing, kayaking and canoeing. "There are some really nice running and biking trails that go all around the lagoons," he says, noting that they extend as far as the Chicago Botanic Garden, about 5 miles away in Glencoe.
Another cyclist and hiker favorite is the Green Bay Trail, a paved path straight through the center of Winnetka. Other leisure and athletic sites include the public Winnetka Golf Club, the private country club Indian Hill, an ice arena and a platform tennis club. "A.C. Nielsen Tennis Center is where a lot of stuff happens," O'Donoghue says. Family friendly sports activities like community leagues are a cherished part of the Winnetka lifestyle.
Green Bay Trail in Winnetka is a great place for residents to enjoy the outdoors.
Lloyd Beach in Winnetka has a boat launch and paddleboard rentals.
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Downtown Winnetka and small businesses
In downtown Winnetka, along Elm Street and Green Bay Road, there's a focus on local businesses. "The downtown has been there a long time and is centered around the Metra," O'Donoghue says. "It's walking-friendly."
Spots for dining include Fred's Garage for sandwiches and tacos; Hometown Coffee & Juice for smoothies and bagels; and Pomeroy, offering French cuisine, brunch and wine tastings.
Ellen's on Elm is a spot to pick out gifts. The shelves are full at The Book Stall, which hosts author events onsite and at public libraries or other local venues. The Grand Food Center and Lakeside Foods stock stables and specialty items to fulfill many a shopping list. For big-box stores like Target and Costco, residents head west of Interstate 94.
Hometown Coffee is a popular spot in Winnetka, especially on a nice day.
Spirit Elephant is one of the fantastic restaurants available in Winnetka.
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Schools divided by levels; New Trier High
Kids may attend public schools in the Winnetka School District 36, which includes Crow Island School, serving prekindergarten through fourth grade; The Skokie School, for fifth through sixth grades; and Carleton W. Washburne School, for seventh and eighth grades. Each has an A grade from Niche. "Winnetka is a progressive education school district," O'Donoghue says. "There's a different philosophy behind the schools." For one, a letter-based grading system is not used until seventh grade.
Next up, A-plus New Trier Township High School enrolls students from Winnetka, Northfield and Glencoe. The upper-level campus is here in Winnetka, and Northfield has the one for freshmen.
Other public school districts in the area include Avoca School District 37, A-minus, and Wilmette School District 39, A. Also in Wilmette is a private option, Loyola Academy, a Jesuit Catholic high school graded A-plus.
New Trier Township High School is an excellent public school located in Winnetka.
Carleton Washburn School in Winnetka has close to 400 students in attendance.
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Three Metra stations, Pace bus routes
The village has the advantage of three Metra stations: Winnetka, Hubbard Woods and Indian Hill. All are on Green Bay Road, with rail service on the Union Pacific North Line, which goes from the city's Ogilvie Transportation Center to Kenosha Station, Wisconsin's only stop. To the west of the village, Interstate 94, or the Edens Expressway, is the quickest route to drive into Chicago.
Pace Suburban Bus Route 423 provides service from Wilmette to Chicago, with stops including Winnetka Station, Winnetka Library, and both New Trier High School campuses. The route goes through Northfield, Glenview, and Niles, and there are L station stops on either end. Route 213 – Green Bay Road hits Winnetka on the way from Highland Park to Howard CTA Station. A paratransit reservation system for portions of north suburban Cook County is also available.
John helps people accomplish their real estate goals. John simplifies the process for first time home buyers, finds off-market deals for seasoned investors and has the best marketing program for sellers. He's been honored by the National Association of Realtors as a "30 under 30" Realtor and has been recognized as a Top Producing Broker by the Chicago Association of Realtors since 2012. He is a contributor to the real estate section of Forbes and has been featured in WSJ, Crain's, Curbed, U.S. News & other publications.
His wife and he reside in the Gold Coast.
Avg. Days on Market: 21 Sales Price v. List Price: 98% Career Transactions: 580+ Est. 2009
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