Winnetka & Glencoe

Winnetka and Glencoe are the wooded, ravine-cut North Shore villages between Kenilworth and Highland Park, with estates that run down to the lake, the Chicago Botanic Garden on Glencoe’s west edge and Writers Theatre in Glencoe’s small downtown. Winnetka has three business districts along the Metra line and the house where Home Alone was filmed; Glencoe is smaller, with a village center on Park Avenue and a public beach at the foot of a ravine. Both have New Trier High School and property values that rank among the highest in Illinois.

Where it is

On the map, Winnetka runs from Kenilworth north to Glencoe between the lake and the Skokie Lagoons; Glencoe continues north to Highland Park, with the Botanic Garden and the Edens Expressway on its west side. Metra’s Union Pacific North line stops at Indian Hill, Winnetka and Hubbard Woods in Winnetka and at Glencoe, about 35 to 45 minutes to Ogilvie. Sheridan Road and Green Bay Road run north-south, Tower Road and Dundee Road cross east-west, and the Edens has exits at Tower, Willow and Dundee.

What to know if you’re moving here

Lots are large, teardowns are common, and the ravines shape what can be built.

• Housing is estates and large single-family homes built from the 1890s on, with typical prices of roughly $800,000 to $6 million and up as a broad editorial estimate as of September 2026.
• Parking is driveways and garages; the Metra lots are permit-only for residents on weekdays.
• Public schools are Winnetka District 36, Glencoe District 35 and New Trier Township High School District 203, with New Trier’s freshman campus in Northfield.
• Property taxes are high, and both villages have stormwater and ravine-protection rules that affect building near the bluffs.
• Metra is the commute, with four stations between the two villages and express trains at rush hour.
• The drawback is cost per square foot and a housing stock where even a modest house on a ravine lot carries an estate-scale tax bill.

What to do if you’re visiting

The Botanic Garden is the day trip; the downtowns are a short walk from the Metra stops and hold the theater, the bookstore and the restaurants.

• On Lake Cook Road in Glencoe, Chicago Botanic Garden has 385 acres of gardens, free admission with paid parking, and Lightscape each winter.
• Glencoe’s downtown pairs a play at Writers Theatre on Tudor Court, now in its 35th season, with dinner or happy hour at Guildhall on Vernon Avenue a block away.
• Coffee and a pressed juice at Hometown Coffee & Juice, the 2018 original at Park and Vernon, is the Glencoe morning routine.
• Glencoe Beach at the foot of Park Avenue has a ravine walk down to the sand, nonresidents pay in summer, and the Skokie Lagoons on the west edge of Winnetka have paddling and a paved loop trail through the forest preserve.
• Downtown Winnetka along Elm Street has The Book Stall, an independent bookstore open since 1940 with about 68,000 titles, and the Greek mezes and flaming saganaki at Avli Winnetka on Chestnut Street, expanded in 2026.
• Burgers and wings in a converted Mobil station at Fred’s Garage, on Green Bay Road at Spruce, come first come, first served, with a big patio in summer.