Inside the North Shore: A Look at Luxury Living Along Chicago’s Lakefront
Chicago’s North Shore has long been synonymous with elegance, heritage, and lakefront living. Today, its appeal to luxury buyers is stronger than ever. Compass Luxury sat down with some of the region’s top agents to explore what continues to set this storied stretch of communities apart, from its architectural richness to its unrivaled access to Lake Michigan and downtown Chicago. Their insights reveal a market defined by sophistication, lifestyle, and enduring demand.
What distinguishes the North Shore as an exceptional destination for today’s discerning luxury buyer?
Paige Dooley | “The North Shore of Chicago is an exceptional destination for discerning luxury buyers thanks to its desirable towns that are community centric, full of scenic beauty along the beaches of Lake Michigan, with lake views, lush tree-lined streets and diverse historic architectural styles. Adding to the appeal is a legacy of top rated schools and cultural, recreational, art and music amenities plus an elegant lifestyle - all with easy access to downtown Chicago via train!”
Corey Green | “Chicago’s North Shore has always stood out to me as the perfect blend of sophistication, character, and lifestyle; the kind of place that truly speaks to today’s luxury buyer. From the lakefront estates and tree-lined streets to the architectural diversity that ranges from classic colonials to modern masterpieces, there’s a timeless quality and vibe here that you just don’t find elsewhere. Each community, whether it’s Lake Forest, Winnetka, or Glencoe—has its own personality, but they all share an unmatched sense of privacy, prestige, and connection. Add in top-rated schools, world class country clubs, and vibrant village centers filled with boutique shops and restaurants, and it’s easy to see why the North Shore continues to draw those who value both sophistication and substance.”
Are there particular neighborhoods or property types currently experiencing heightened demand?
Aaron Share | “Glenview has emerged as one of the North Shore’s most dynamic luxury markets. Demand remains intense, with sale-to-list ratios exceeding 100% and days on market steadily declining year over year. High-end single-family homes are achieving record prices, narrowing the long-standing gap with neighboring Wilmette and Winnetka as more buyers recognize Glenview’s exceptional value. The appeal is clear. Larger lots, relatively lower taxes, convenient commuter access, and top-rated schools continue to attract affluent buyers. The village’s ongoing downtown revitalization, which includes new restaurants, infrastructure improvements, and everyday amenities, is further adding to its momentum. Together, these factors are fueling sustained demand and elevating Glenview’s position among the North Shore’s premier luxury communities.”
Coco Harris | “On Chicago’s North Shore—and particularly within the New Trier Township communities—land continues to hold exceptional value due to its inherent scarcity. With Lake Michigan defining our eastern border, the availability of larger parcels is naturally limited. As home prices have risen in recent years, so too has the cost of land, which has significantly increased the overall price of new construction. Demand for newly built homes far exceeds the supply of larger lots available to build upon. To complement this trend, we’re also seeing remarkable demand for beautifully renovated homes. With time now considered the ultimate luxury, today’s buyers place immense value on properties that have been thoughtfully redesigned using premium materials and timeless finishes. These turnkey homes—those that far surpass “builder-grade” quality—offer a level of ease and sophistication that appeals deeply to North Shore buyers seeking a move-in-ready lifestyle without compromise.”
What upcoming opportunities should prospective buyers in the North Shore anticipate?
Jacqueline Lotzof and Stephanie Malk | “Luxury buyers on the North Shore can anticipate opportunities in quality — not just quantity. Many homeowners are upgrading or relocating, bringing some truly extraordinary properties to market. The focus this season is on homes with lifestyle value: outdoor space, design integrity, and proximity to the lake.”
Joanne Hudson | “I’m seeing many more upper-bracket homes ($3M+) hit the market this year, which is great for buyers. In 2024, 71 luxury homes were listed and sold in the North Shore; this year that number has risen to 124, giving my clients more options and stronger leverage.Today’s luxury buyers are even more discerning and feel less pressure to rush, knowing new listings are coming. Still, exceptional properties sell within days, so serious buyers must be ready to move quickly. Some clients are open to full renovations, but economic uncertainty and the associated trepidation has others waiting for turnkey homes in excellent condition. Across the board, buyers continue to prioritize top locations and quality—and are willing to wait for the right fit.”
How do you foresee the luxury home market evolving in the North Shore over the coming year?
Meg McGuinness and Katie Hauser | “We have noticed that our buyers searching in the luxury market, and some have been searching for a few years, have heightened expectations. They prefer homes that are turn-key. Even understanding the low inventory, they are less likely to settle for a luxury price tag on a home that needs extensive updates and work. We are advising our sellers to prepare for more competition and prepare their homes. This often involves staging, painting, refinishing floors, and extensive decluttering. Houses that are well maintained and presentable will earn the luxury price tag. Our communities on the north shore continue to grow with luxury retail and restaurants drawing people to the neighborhoods. The schools remain excellent, access to the city is great and of course proximity to the lakefront remain hallmarks of Chicago’s North Shore. Buyers are willing to invest in this desirable lifestyle for a home that is truly move-in ready.”
Noah Leavy | “I expect the North Shore luxury market to remain tight over the coming year, driven by limited inventory and steady demand. Buyers continue to come from the city, other suburbs further west, and within the North Shore itself as many look to move up. With lifestyle and convenience top of mind, well-presented, move-in-ready homes in desirable locations will continue to attract strong interest. Even if the market does stabilize, I anticipate that premium luxury properties will remain competitive and hold their value.”
How would you characterize the lifestyle of a North Shore resident? How do they typically spend their time?
Meredith Pierson | “The North Shore offers a seamless shift from the city’s energy to a more grounded, family-centric rhythm—without sacrificing sophistication. Residents gravitate toward the lakefront, local boutiques, and standout dining, spending their days in a community where supporting local businesses and enjoying time with family is simply part of the culture.”
Alissa McNicholas | “The North Shore lifestyle is all about balance – connection to nature, community and convenience. We are surrounded by the lake, open lands, and tree line streets, yet just a quick train ride from the city. It’s a place where families thrive, neighbor’s wave and people genuinely care the beauty of where we live.”
Which local events, traditions, or cultural experiences contribute to the North Shore’s unique character?
Janet Borden | “The best North Shore experience, tradition / event that comes to mind is Ravinia Festival in Highland Park. World class music under the stars with a glass of wine in hand and a gourmet picnic spread! This is a beloved summer tradition on the North Shore since 1904 and a range of artists from Tony Bennett, to 50 Cent, Yo-yo Ma to Santana, there is just nothing like it.”
Beth Alberts | “I think Ravinia Festival in Highland Park defines the North Shore’s unique character. It’s so special to be able to see world renowned acts literally in our backyard. Close contenders would be our lakefront and the botanic gardens.”
Elizabeth Wieneke | “The North Shore offers a unique lifestyle filled with culture, community, and natural beauty. From lectures at Northwestern, summer concerts at Ravinia, and leisurely days at Lake Michigan's pristine beaches or exploring the Chicago Botanic Garden, local art festivals and farmers markets to holiday tree lighting ceremonies and dinners at many fine restaurants. The North Shore seamlessly blends sophistication with small-town charm, embodying the essence of refined living on Chicago's lakefront.”
Are there any favorite restaurants, destinations, or hidden gems in the area that you would recommend?
Dave + Amy Chung | “We have so many hidden gems it is hard to pick just one. We love heading up to La Plancha Loca in Highwood for the best tacos on the north shore. Or Ami Jerusalem that has the fluffiest rice. Non-Food related hidden gems: I love to take a break from the cold winters by booking an hour in the Infrared Sauna at Sol Luna in Winnetka. It’s great to book with a friend for a cozy catchup or bring a book. I always feel warmed from the inside out and ready to face the cold again.”
The Marina & Andy Team | “Favorite restaurants, Le Colonial, Folia, Elawa Farm Café. Hidden gems are Elawa Farm, Lake Forest Open Lands, & Forest Park!”
What aspects of working in North Shore luxury real estate inspire you most?
Sally Mabadi | “I specialize in selling historic homes so the stunning architecture, the natural beauty of the North Shore, and the wonderful lifestyle the North Shore provides inspire me the most. The homes are incredible; each historic property is unique so you can really make your home something special that reflects you and how you live. In addition, the quality of the schools, community amenities, proximity to Chicago, the arts, and natural beauty of our beautiful lake, beaches and forest preserves make this the best place in the world to live!”