Idyllic in every sense of the word

Welcome to Winnetka

Perfectly perched on Lake Michigan, living in Winnetka offers a postcard perfect lifestyle. Beautiful in landscape and architecture, it's tree-lined streets and narrow roads perfectly frame its beautiful residential dwellings. Highly touted as the "tree streets," it's most central residential enclave with streets named after what else?...trees, features a beautiful array of homes stretching from Hibbard between Green Bay Roads. All throughout the village, you're to find homes of varying size with stately architectural. The homes and the lots become more sprawling and grand when heading east towards Sheridan Rd and the shores of Lake Michigan. Affluent Winnetka attracts a highly educated homeowner wanting a quiet suburban lifestyle.

Featuring a downtown shopping district which can simply be described as timeless, this town offers superb location amenities to the Edens Expressway, Sheridan and Green Bay Roads, and a downtown Metra station. You'd be hard pressed to find a more lovely fall landscape outside of New England that mirrors Winnetka's. Afforded the finest of most things, the K-12 school system rivals those of any across the nation. Basked in nature, its residents have direct access to wooded bike trails, quiet kayak rides in the Skokie Lagoons, and multiple public Lake Michigan beaches. This wealthy North Shore village is one of the most desirable suburban destinations perched nearby a large metropolitan city in the country. 

What to Love

  • Quiet, peaceful landscapes
  • Routinely voted at or near the top of best small towns in America
  • Superb public and private schooling
  • Picturesque throughout
  • Old world charm downtown commercial district

What to Do

Bordered by Erickson Woods to its west, there's ample nature trails and relaxation enjoyed year round. The North Shore boasts the Skokie Lagoons, one of Chicagoland's finest outdoor nature experiences which many recent transplants wouldn't know about. Maintained by Cook County and originally commissioned by the FDR administration to improve drainage for the benefit of its residents, this 894-acre man-made waterway consists of 7 lagoons connected by channels to the Skokie River and the Chicago Botanic Gardens to its north. A lovely landscape for any who enjoy a day full kayaking, fishing, biking, hiking, or just sitting peacefully in nature. It's not to be missed.

The village's park district itself, runs its own 240+ acres of parkland, much of which consists five beaches. With boat launches, rolling bluffs, pleasant walking trails, and even a dog beach, the taxpaying dollars - while significant - go towards the worthy cause of maintaining a timeless residential experience. 

And Winnetka's picturesque streets are displayed in full effect at its multiple shopping districts. With countless boutique shops, high-end retailers, and dining options, it's no surprise Hollywood has quietly filmed some of the last half century's most popular films using this quaint backdrop - most notably, Chicagoland's most famous director, John Hughes, whose affinity towards Winnetka and the North Shore was showcased all throughout his films. As this author writes these remarks a week before Thanksgiving kicks off the holiday season, it's impossible to not mention the all-time family classic Home Alone. Winnetka is a special town which its residents are proud to call home.


District 203's New Trier High School, which consists of two separate campuses in neighboring towns Wilmette and Northfield, is regularly acknowledged within the state and nationally as a top-tier education designation with a 98% graduation rate and a 96% college enrollment rate. Every school year, it welcomes its new students from junior highs not only from Winnetka's District 36, but also neighboring suburbs Wilmette, Kenilworth, Glencoe, Northfield, and small pockets of Glenview and Northbrook. 

District 36 is where the village's K-8 learners prepare for high school. Elementary: Hubbard Woods, Crow Island, Greeley / Middle: The Skokie School / JH: Washburne


Incorporated: 1869

Population: ~12,500

12-mo Median Home Price: $1,275,000 (as of 9/1/2021)

Search Homes

The Location

Work With Eric

Client-focused and well-educated in all things residential real estate, Eric successfully guides his clients throughout Chicago's Northside and the suburban North Shore, from start to finish. It's his passion. It's his purpose.

Let's Connect

Follow Me On Instagram