Kate Barnett Real Estate Team

Winnetka Market Trends

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Nestled along the shores of Lake Michigan, Winnetka is Native American for “beautiful land.”

Ivy-draped estates, quaint shops and cozy restaurants cluster the tree-lined streets of this North Shore hamlet.  Along the lake, a series of public beaches, boat launches, parks and athletic fields add to the ambiance.

Also home to New Trier High School, one of the nation’s most elite public schools, this bastion of tranquil, elegant living has a definite “old money” feel.

Accordingly, this kind of charm comes with a price tag.  Winnetka recently ranked #4 in Money Magazine’s 25 Top-Earning Towns, with a median household income of $195,879.


Winnetka is located approximately 16 miles north of downtown Chicago, along the shores of Lake Michigan.

To the south are Wilmette and Kenilworth, to the west are Northfield and Northbrook, to the north is Glencoe, and to the east is the Lake.


Population (2000)
Total 12,419
Density 3,242 people/square mile
White: 96.3 percent
Black: 0.2 percent
Hispanic: 1.3 percent
Asian: 2.4 percent
Other: 0.7 percent

Median per capita income: $84,134

Source: U.S. Census, Record Information Service


Winnetka’s first settlers, Erastus Patterson, his wife Zeruah and his five children, arrived in 1836.  The family built a tavern to serve stagecoach passengers traveling the Green Bay Trail between Fort Dearborn in Chicago and Fort Howard in Green Bay, WI. Open lumber wagons making the 500-mile round trip offered space for both mail and passengers, and wayside inns like Patterson Tavern were a welcome respite from the harsh conditions of the trail.  

In 1853, Charles and Sara Peck moved to the region.  Working in tandem with Chicago & Milwaukee Railway president Walter Gurnee, Charles platted and subdivided 300 acres of land.  Sarah named the new community Winnetka, after a Native American phrase meaning “beautiful land.”  Winnetka first incorporated as a village in 1869, with a population of 450.  

In 1855, the Chicago & Milwaukee Railway was built through the village, and Metra trains still operate along its lines today   A second railroad, the Chicago, North Shore & Milwaukee interurban was constructed in the early 1900s, but its tracks were removed in the 1950s and the land was repurposed as the 16-mile Green Bay Trail bicycle path.

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Winnetka is home to beautiful, sprawling lakeside manors and ivy-splashed villas.  Its shady lanes are home to estates designed by famous architects such as David Adler, Howard Van Doren Shaw and John S. Van Bergen.  The most expensive properties abut Lake Michigan, and offer private beaches and spectacular views.

Search Winnetka Real Estate.


Winnetka commuters can catch Metra’s Union Pacific North Line at Elm Street, Indian Hill or Hubbard Woods station.  The area is also served by Pace bus and the Edens Expressway (I-94).


Winnetka schools have long received national recognition for excellence.  Winnetka is served by Winnetka School District 36 and New Trier Township High School District 203.

Grades K-4 are served by public schools Crow Island School, Samuel Sewall Greeley School, and Hubbard Woods School. Grades 5-6: The Skokie School, Grades 7-8: Carleton Washburne Middle School.

Sacred Heart and Saints Faith, Hope and Charity are Catholic pre-K through 8.

Most of the area’s high school students attend renowned New Trier High School, with Freshmen Northfield campus and Sophomores, Juniors, Seniors at the Winnetka campus.

The North Shore Country Day School is a coeducational, college-prep school of 490 students Kindergarten through Grade 12.

Winnetka is also home to several specialized schools, including the French Institute of the North Shore, the Hadley School for the Blind and the Music Institute of Chicago.


Trifecta Grill (501 Chestnut St., (847-441-1700) is a great trendy restaurant and bar is new to the Winnetka area. They have outside seating, a great variety of vines, stylish decor, friendly staff and a hand crafted cocktail list full of refreshing drinks.


Avli Estiatorio (566 Chestnut St.) is Greek for “the courtyard restaurant.”  Enjoy delicious Greek food surrounded by friendly people in a relaxed atmosphere.  The menu offers classics like Saganki and Dolmades, but also some regional dishes you might only find in Athens, like fresh octopus and greens with oil and lemon.

Chicago Magazine calls Chef Michael Lachowicz of Restaurant Michael (64 Green Bay Rd.) the “last butter and cream man standing.” Seasonally inspired French fare abounds at this refined eatery, from a salad of warm pistachio-dusted goat cheese over honey truffle-dressed baby greens to a stunning sautéed foie gras medallion served with candied huckleberries. Upon request, the Chef can also produce dishes to suit younger palates.

The Original Green Bay Café (568 Green Bay Rd.) is the place to go for friendly service, rustic décor and great omelets and pancakes.  Seasonal specials also regularly appear on the chalkboard of this snug breakfast nook.  Must-haves include the bread pudding French toast and the tamale corn flapjacks.


Winnetka has 23 community parks, 3 swimming beaches, a boating beach, a dog beach, an 18-hole public golf course and an outdoor ice rink.  Details can be found on the Winnetka Park District website.

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