Winnetka is one of those rare North Shore villages that immediately feels like home. Just 16 miles north of downtown Chicago, this lakeside gem blends timeless architecture, beautiful tree-lined streets, and a deep sense of community pride. Whether you’re drawn to its top-rated schools, walkable shopping districts, or peaceful lakefront, Winnetka is a place where every neighborhood feels special in its own way.
As a local Realtor who loves helping clients find their perfect corner of the North Shore, I often describe Winnetka as a “village of neighborhoods.” Each pocket has its own personality — from the quiet, wooded streets near Hubbard Woods to the stately homes near the lake. Let’s take a closer look at what makes each area shine — and where the local schools fit in.
Hubbard Woods
Hubbard Woods is one of Winnetka’s most vibrant and walkable areas. Centered around the Hubbard Woods Metra station and the charming shopping district on Green Bay Road, this neighborhood blends historic architecture with modern convenience.
You’ll find classic Tudor and Colonial homes alongside newer construction, all surrounded by tall trees and close to Hubbard Woods Park and Tower Road Beach. On weekends, locals love grabbing coffee at Hometown Coffee & Juice or exploring nearby boutiques.
Families here are zoned for Hubbard Woods Elementary School (K–4), part of Winnetka School District 36, known for its strong academics and whole-child philosophy.
East Winnetka and the Elm Street District
East Winnetka offers that quintessential “by-the-lake” feel — with winding streets, elegant homes, and a quiet charm that’s hard to beat. Many homes are within walking distance of Elder Lane Beach and Centennial Park, and you can stroll to the boutiques, cafés, and restaurants of the Elm Street business district.
This neighborhood captures the best of Winnetka living: lake breezes, local charm, and convenience.
Families here often attend Greeley Elementary School (K–4) before moving on to Skokie School (5–6) and Carleton W. Washburne School (7–8).
Indian Hill
Tucked near the southern edge of the village, Indian Hill offers a peaceful, residential feel with easy access to the Indian Hill Metra station and Indian Hill Country Club. Many homes here are classic Colonials and English manors set on wide lots with mature landscaping.
Residents enjoy proximity to both Winnetka’s village center and downtown Kenilworth — ideal for those who appreciate quiet surroundings with a touch of urban access.
Some areas near Indian Hill feed into Avoca School District 37, which includes Avoca West Elementary (K–5) and Marie Murphy School (6–8), before students continue on to New Trier High School.
Forest Glen
Forest Glen is a small, close-knit neighborhood known for its traditional Colonial-style homes and neighborly feel. Many homes were built in the 1930s and ’40s, creating a cohesive architectural story that feels timeless.
Tree-lined streets and a strong sense of community define Forest Glen — neighbors often know one another by name, and seasonal gatherings are a cherished tradition.
Most homes here are zoned to Crow Island Elementary School (K–4), one of Winnetka’s most architecturally unique schools and a National Historic Landmark for its innovative design.
Winnetka Heights
Situated between Pine and Westmoor, Winnetka Heights sits on some of the highest ground in the village — offering beautiful elevation and stately views. The area is defined by larger homes, deep setbacks, and mature landscaping. It’s quiet yet connected, just a short distance from both the village center and Hubbard Woods.
Like much of the village, Winnetka Heights feeds into Winnetka School District 36 schools and New Trier High School.
Schools That Define the Community
Winnetka is known across the North Shore for its outstanding public school system, innovative learning programs, and community support for education. Here’s how it’s structured:
Public Schools
Winnetka School District 36 (K–8)
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Greeley Elementary (K–4)
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Hubbard Woods Elementary (K–4)
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Crow Island Elementary (K–4)
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Skokie School (5–6)
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Carleton W. Washburne School (7–8)
After eighth grade, all District 36 students attend New Trier High School (District 203) — one of the top-ranked public high schools in the nation, located right here in Winnetka.
A few southern portions of Winnetka fall within Avoca District 37, serving Avoca West Elementary and Marie Murphy Middle School, both highly rated. A small southeastern pocket is part of Kenilworth School District 38 (Sears School).
Private and Parochial Options
Winnetka also offers excellent independent and parochial schools:
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North Shore Country Day School (JK–12) – A college-prep independent school emphasizing character and creativity.
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Sacred Heart School (PreK–8) – A Catholic community school in the Hubbard Woods area.
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Faith, Hope & Charity School (Preschool–8) – A beloved Catholic school in East Winnetka.
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La Petite École de Chicago (Winnetka Campus) – A bilingual French-English program.
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Hadley Institute for the Blind and Visually Impaired – Providing education and support to visually impaired learners worldwide.
Why People Love Living in Winnetka
Beyond its picture-perfect homes and excellent schools, Winnetka has a true sense of community. From the Fourth of July parade and local block parties to the Farmers Market and concerts in the park, there’s always something happening that brings people together.
Its three charming business districts — Indian Hill, Hubbard Woods, and Elm Street — are filled with independent shops, coffee spots, and restaurants, all designed to make everyday errands feel a little more enjoyable. And with several Metra stations running through town, getting to downtown Chicago is simple and stress-free.
Winnetka also boasts four stunning beaches, 11 parks, and a dedication to preservation that keeps its character intact year after year.
Final Thoughts
Whether you’re looking for a historic home near the lake, a family-friendly street close to schools, or a quiet cul-de-sac surrounded by trees, Winnetka offers something for everyone.
It’s a community that values connection, tradition, and a slower pace — while still being minutes from downtown Chicago. That’s what makes it one of the most sought-after places to live on the North Shore.
If you’re thinking about making Winnetka your home, I’d love to help you find the neighborhood that feels just right.
Reach out anytime — let’s find your perfect North Shore fit.
