🏡 Lake Forest vs. Winnetka: Which North Shore Suburb Wins the Luxury Showdown in 2025?

The Biggest News Jason Rosenberg
May 9
3 min read

So, you’re ready to drop seven figures on a house, but you’re torn between Lake Forest and Winnetka—two of Chicago’s swankiest, most scenic, and let’s be honest, most judgmental zip codes. One offers peaceful lakefront estates with serious old-money vibes. The other? A walkable, prestige-packed town where yoga pants are basically a status symbol.

Let’s pit them against each other in a friendly-but-fierce suburban showdown to help you decide which North Shore paradise is right for you.

🌳 The Vibe

Lake Forest is quiet, elegant, and has a deep appreciation for legacy—think ivy-covered estates, equestrian properties, and neighbors who still refer to Lake Michigan as “the lake.” It’s where privacy reigns, lawns are mowed by silent groundskeepers, and golf carts may outnumber Priuses.

Winnetka, on the other hand, has more of a "country club meets SoulCycle" energy. It’s buttoned-up but busier. You’ll spot Range Rovers doing the school drop-off, dogs in sweaters at farmers markets, and local moms with Peloton usernames more competitive than their kids' SAT scores.

🛍️ Downtown Scene

Lake Forest has Market Square, a charming and historic shopping district where you can buy cashmere, a $22 sandwich, or an antique globe you didn’t know you needed. It's cozy, curated, and very “we summer in Nantucket.”

Winnetka has a buzzing downtown with boutiques, trendy restaurants, and access to everything from eyebrow threading to overpriced acai bowls. Plus, it’s easier to walk from one shop to the next without getting hit by a landscaping truck.

💰 Real Estate Prices

Let’s talk money—because these two suburbs aren’t giving anything away.

Lake Forest: You get more house and yard for your buck. Think 6,000+ square feet, private driveways, and actual horse barns.Median Home Price (2025): ~$1.4MPrice Per Sq Ft: Around $330–$400
Winnetka: Homes are typically smaller but pricier per square foot thanks to walkability, prestige schools, and that New Trier glow-up.Median Home Price (2025): ~$1.6MPrice Per Sq Ft: Around $500–$600+

🚆 The Commute

Winnetka is a commuter’s dream, with multiple Metra stops and a ~30-minute train ride downtown. You’ll be home before your boss even leaves the Loop.

Lake Forest has a longer, ~50–60-minute train ride, which gives you just enough time to finish your audiobook, answer three emails, and mentally prepare to see no one for the next 12 hours.

🏫 Schools

This one’s a heavyweight battle.

Lake Forest High School is elite, well-funded, and known for arts, athletics, and a tight-knit environment.
New Trier High School in Winnetka is consistently ranked among the top public schools in Illinois—academic rigor, endless electives, and enough clubs to rival a Big Ten college.

🏘️ Architecture & Housing Styles

Lake Forest is home to sprawling estates and timeless architecture—Georgian Revivals, Shingle Style homes, and ivy-covered mansions that look like they should be in Town & Country magazine.

Winnetka mixes old-world elegance with new construction charm. You’ll see Tudors next to modern farmhouses, all impeccably maintained and usually with kitchen islands the size of Lake Michigan.

🎯 The Final Verdict

Choose Lake Forest if you want privacy, green space, and to live somewhere where “quiet luxury” is a way of life.
Choose Winnetka if you want walkability, public school prestige, and to feel like you're living in a Nancy Meyers movie with better Wi-Fi.

Either way, you’re winning. Just bring your checkbook and maybe a golden retriever.