Communities · North Shore
Winnetka Real Estate
A lakefront village less than 20 miles north of Chicago, with three Metra stations and three business districts. Here's what housing costs, how the schools and the commute work, and where the market landed in 2025.
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Winnetka was incorporated in 1869. The village credits its name to Sarah Peck, who chose a Native American phrase thought to mean "beautiful land." It sits on Lake Michigan between Kenilworth and Glencoe, and its shops and restaurants are spread across three business districts, Elm Street, Hubbard Woods and Indian Hill, each with its own Metra station.
Much of the housing is older, much of it built before the Second World War, with newer houses mixed in, many of them built on older lots. Crow Island School, a public elementary school, was designated a National Historic Landmark in 1990. Film fans may know the village from Home Alone: the house used in the film is a private residence on Lincoln Avenue, one of several local houses in our iconic movie homes feature.
It is a smaller market than Wilmette or Evanston: about two hundred homes change hands in a typical year, nearly nine in ten of them detached houses. The snapshot below is the full 2025 closed record, not a sample.
2020 Census and 2020–2024 American Community Survey (5-year estimates). The Census Bureau reports Winnetka's median household income only as "$250,000+", its top category.
The market in brief
What Winnetka housing costs
Every closed sale recorded in Winnetka in 2025: detached houses, townhouses and condominiums. Two vacant-land sales excluded.
Source: MRED closed sales, January–December 2025. Current as of the 2025 year end.
With about two hundred sales a year, a handful of very large sales can move Winnetka's averages, so the medians are the better guide. Half of the detached houses sold in 2025 were built before 1940. For this month's prices, supply, showing activity and the age of homes selling now, and what they mean for buyers and sellers, use the market statistics page.
Winnetka market statistics
Current price, inventory, months of supply and showings, with live MRED charts and a plain-language read of what changed.
See the Market StatisticsThe best month to sell in Winnetka
667 Winnetka houses that went under contract from 2023 to 2026, sorted by the month they were listed.
Read the StudySchools
District 36, then New Trier
Most of Winnetka is served by Winnetka Public Schools District 36. Its three elementary schools, Crow Island, Greeley and Hubbard Woods, serve kindergarten through fourth grade, and each home is assigned to one of them by address. District 36 students then attend The Skokie School (grades 5–6) and Carleton Washburne School (grades 7–8).
Part of Winnetka, including the Woodley Woods area, is served by Avoca School District 37 instead (Avoca West, then Marie Murphy School).
Both are sender districts to New Trier Township High School District 203: first-year students attend the Northfield Campus, and grades 10–12 the Winnetka Campus on Winnetka Avenue. District-level results are on the Illinois Report Card for District 36, District 37 and New Trier.
Private options in the village include North Shore Country Day School on Green Bay Road, which runs from junior kindergarten through 12th grade, and Saints Faith, Hope and Charity, a Catholic parish school.
For more detail: preschools in Winnetka.
In Winnetka, the elementary school follows the address. Check it before you write an offer.
District 36 assigns its three K–4 schools by attendance boundary, and part of the village, including the Woodley Woods area, is in a different district. Boundaries can change, so confirm current attendance for a specific address with the district before you buy. Our Search by Elementary School tool helps you narrow the search first.
Watching Winnetka? Get Winnetka Coming Soon alerts →
Getting to the city
The Winnetka commute
Winnetka has three stations on Metra's Union Pacific North line: Indian Hill on Green Bay Road at the south end of the village, Winnetka on Elm Street downtown, and Hubbard Woods on Gage Street to the north. From the Elm Street station, scheduled weekday service to Ogilvie Transportation Center in downtown Chicago takes 37–42 minutes. Most trains take 42. Five weekday-morning trains skip stops and run in 37.
From Indian Hill the scheduled trip is 40 minutes, and from Hubbard Woods 45, but not every weekday train stops at those two stations. On weekends every train stops at all three, taking 40, 42 and 45 minutes from Indian Hill, Elm Street and Hubbard Woods. By car, the Edens Expressway is a short drive west, and downtown Chicago is less than 20 miles away.
Outside
Five beaches, a public course and year-round tennis
The Winnetka Park District runs twenty-five parks, five beaches and a boat launch.
The village's Lake Michigan beaches are Elder Lane, Maple Street, Tower Road, Lloyd and Centennial. The Park District's Waterfront 2030 plan, adopted in 2016, is its guide for future work on all five; check the Park District for each beach's current season before you plan a visit.
On Hibbard Road, the Winnetka Golf Club has a championship 18-hole course and a nine-hole par-3 course, and next door the A.C. Nielsen Tennis Center has eight indoor and twelve outdoor courts. The Park District also runs the Winnetka Ice Arena and platform tennis courts.
Landmarks and the arts
A community house, a landmark school and a history museum
The Winnetka Community House on Lincoln Avenue, founded in 1911, hosts classes, events and programs, and its second floor is home to most of the North Shore Art League's programming. The Winnetka Historical Society runs a museum on Linden Street, open Tuesday and Thursday afternoons, and the Winnetka branch of the Winnetka-Northfield Public Library District is on Oak Street. Crow Island School, still a District 36 elementary school, is a National Historic Landmark.
The Music Institute of Chicago has a campus on Green Bay Road. Nearby, the North Shore Center for the Performing Arts is a short drive into Skokie, and Ravinia is up the Union Pacific North line in Highland Park.
Downtown and around
Three business districts and a Saturday market
Winnetka's shops and restaurants are spread across its three business districts, so this is a sample, not a directory. Around Chestnut Street are Soupicurean for breakfast and lunch, True Juice for smoothies, soups and salads, Fred's Garage, Avli for Greek food, Tocco for casual Italian and Spirit Elephant, which is vegan. Near Lincoln Avenue and Elm Street are Stacked & Folded, Hometown for coffee, breakfast and lunch, and 501 Local, with patio dining. In Hubbard Woods: Grateful Bites for pizza, Once Upon a Bagel, Kyoto for sushi and Mino's for Italian.
From June through October, the Winnetka farmers market runs on Saturday mornings in the Elm Street train station lot.
Tools and resources
Built for how people actually buy here
Six things worth using before you write an offer in Winnetka.
Before it reaches the market
Coming Soon listings are marketed before their broader public-market launch, giving buyers an earlier opportunity to learn about a home. Buyers can express interest and make offers during this stage; whether a seller considers an offer before the broader launch is up to the seller. Compass Private Exclusives are not publicly marketed while they are offered as Private Exclusives; some later come to the open market. The two are different, and neither guarantees access to a particular home.
Search Coming Soon → How Private Exclusives work →Search by elementary school
In Winnetka the elementary school follows the address. Start with homes listed by elementary school, then confirm the current boundary with the district.
Search Now →Walk to train
Homes within genuine walking distance of Winnetka's three Metra stations, not "close-ish by car."
View Homes →New construction guide
Finishes, builder reputations and which locations hold value on the North Shore, Winnetka included.
View the Report →Market Ready Concierge
Compass's current program for financing pre-sale preparation, through Notable. Fees and interest apply and approval isn't guaranteed. We'll walk you through whether it fits.
The Insider's Guide
Our own guide to the North Shore, Winnetka included: schools, commutes, taxes and what each town is actually like to live in. Free.
Get the Guide →Working with us
The 6-Point Strategic Buyer Program
What we actually do between "I like this house" and "here are the keys."
Pre-market access
We monitor multiple sources — including our professional networks, Top Agent Network, Compass Coming Soon and other permitted pre-market opportunities — so your search is not limited to active public listings.
Comprehensive value analysis
A detailed read on both comparable sales and current market conditions, so you know what a house is worth before you name a number.
Strategic negotiating
Lisa is a licensed attorney and former litigator. In multiple-offer situations, we focus on both price and the terms that can affect a seller's decision.
Extra intel
We vet every home and its location for flooding history, walkability, commuting and anything else that could affect your enjoyment or your resale. Nothing is ever guaranteed, but you'll go in informed.
Innovative techniques
When nothing on the market fits, we go looking. Handwritten notes to owners in the streets and buildings you want, and geographically targeted advertising to reach homeowners who are thinking about selling but haven't listed.
Local expertise
We live on the North Shore, drive these streets daily, sit on community boards and have children in local activities. That produces the kind of anecdotal knowledge that never makes it into a listing sheet — and it means we can preview homes quickly for busy or out-of-town buyers.
Thinking of selling
Four steps, in order
- Start with the online estimate — it shows recent closed prices for homes near yours.
- Then get a real price analysis — a strategic, complimentary read on your specific house, which is a different thing from an algorithm's guess.
- Look at whether Market Ready Concierge or a private launch helps — financing for pre-sale work (fees and interest apply), or testing the market before the clock starts.
- Then go to market — photography, staging and a launch timed to the week that suits your house, not the calendar.
New on the market
New Winnetka listings added in the past 7 days
Residential listings added in the past 7 days · $100K–$15M · with photos
Listings courtesy of Midwest Real Estate Data, LLC (MRED) as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and is deemed reliable but not guaranteed. Some listings have been excluded from this website. Full disclosures
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