Chicago’s North Shore Real Estate in 2025: A Town-by-Town Guide to Evanston, Wilmette, Winnetka, Glencoe, Kenilworth, Highland Park, Lake Forest & Lake Bluff

Thinking about moving to Chicago’s North Shore in 2025? Whether you’re dreaming of lakefront luxury, award-winning schools, walkable downtowns, or just more space for your family, Chicago North Shore real estate offers something for every lifestyle. In this updated 2025 guide, we’ll break down the differences between each North Shore suburb—from Evanston to Lake Bluff—with the latest average home prices, days on market, and local insights to help you choose the perfect fit.

What Is Chicago’s North Shore?

Chicago’s North Shore consists of a group of highly desirable suburbs hugging the Lake Michigan shoreline, just north of downtown Chicago. Known for their top-rated schools, beautiful homes, strong community vibes, and easy commutes to the city, the North Shore is one of the most popular areas for buyers relocating to Chicagoland.

Detailed Guide to North Shore Towns (2025 Market Data)

Evanston, IL

• Average Home Price (July 2025): $583,500

• Median Days on Market: 46 days

• Population: ~77,000

• School Districts: Evanston/Skokie District 65, Evanston Township High School 202

• Vibe: Urban-suburban mix with a lively arts scene, historic homes, and a vibrant downtown. Evanston is the only North Shore community with both Metra and CTA ‘L’ train access, making it incredibly commuter-friendly.

• Highlights: Home to Northwestern University, over 80 parks, extensive bike paths, and a bustling restaurant scene. Residents enjoy walkability, cultural diversity, and direct access to Lake Michigan beaches.

• Why Move Here: Perfect for those who want city excitement with a neighborhood feel. Offers condos, single-family homes, and historic lakefront properties.

Wilmette, IL

• Average Home Price (July 2025): $900,000

• Median Days on Market: 45 days

• Population: ~27,000

• School Districts: Wilmette District 39, New Trier Township High School District 203

• Vibe: Classic, charming suburb with top-ranked public schools, tree-lined streets, and a welcoming community.

• Highlights: Famous for its beautiful Gillson Park beach, the striking Bahá’í House of Worship, and a walkable downtown filled with boutiques and local eateries. Residents enjoy family-friendly festivals, summer concerts, and a robust park district.

• Why Move Here: If you’re looking for Chicago North Shore real estate with strong resale value, great schools, and an active lifestyle, Wilmette is a top pick.

Winnetka, IL

• Average Home Price (July 2025): $1,150,000

• Median Days on Market: 42 days

• Population: ~12,500

• School Districts: Winnetka District 36, New Trier Township High School District 203

• Vibe: Prestigious, elegant, and known for luxury lakefront estates and picture-perfect neighborhoods.

• Highlights: Winnetka offers three beautiful beaches, a historic downtown, and the famous “Home Alone” house. The village is filled with grand homes, lush landscaping, and top-tier schools.

• Why Move Here: Ideal for luxury buyers, executives, and those seeking a serene but social community with quick Metra access to the city.

Glencoe, IL

• Average Home Price (July 2025): $1,120,000

• Median Days on Market: 48 days

• Population: ~8,900

• School Districts: Glencoe District 35, New Trier Township High School District 203

• Vibe: Upscale, intimate, and tucked away among mature trees and green spaces.

• Highlights: Just minutes from the renowned Chicago Botanic Garden and the Writers Theatre. Glencoe boasts quiet residential streets, sandy beaches, a golf club, and a charming village center.

• Why Move Here: For those seeking privacy, small-town charm, and easy Metra access, Glencoe delivers classic North Shore tranquility.

Kenilworth, IL

• Average Home Price (July 2025): $1,400,000

• Median Days on Market: 38 days

• Population: ~2,400

• School Districts: Kenilworth School District 38, New Trier Township High School District 203

• Vibe: Ultra-exclusive and peaceful, Kenilworth is known for its legacy estates and secluded setting.

• Highlights: With only about 800 homes, Kenilworth offers some of the North Shore’s most coveted real estate. The village is almost entirely residential, with impressive historic mansions and easy lake access.

• Why Move Here: Perfect for buyers prioritizing privacy, prestige, and beautiful architecture in a small, tight-knit village.

Highland Park, IL

• Average Home Price (July 2025): $780,000

• Median Days on Market: 44 days

• Population: ~30,200

• School Districts: North Shore School District 112, Township High School District 113

• Vibe: Artistic and diverse, Highland Park combines suburban comfort with a strong creative spirit and community pride.

• Highlights: Famous for the Ravinia Festival (summer music under the stars), a walkable downtown, 800+ acres of parks, and direct Metra service. The city has a variety of home styles, from vintage bungalows to stunning lakefront estates.

• Why Move Here: Families, music lovers, and anyone wanting a dynamic, walkable North Shore lifestyle love Highland Park.

Lake Forest, IL

• Average Home Price (July 2025): $749,000

• Median Days on Market: 46 days

• Population: ~19,400

• School Districts: Lake Forest School District 67, Lake Forest High School District 115

• Vibe: Historic, grand, and distinctly elegant, with classic estates and rolling lawns.

• Highlights: Beautiful beaches, historic Market Square, elite private and public schools, country clubs, and Lake Forest College. The community is known for stunning architecture and a “retreat from the city” feel while still being Metra-accessible.

• Why Move Here: Ideal for those who value space, quiet, and a strong sense of tradition, with quick access to outdoor recreation.

Lake Bluff, IL

• Average Home Price (July 2025): $670,000

• Median Days on Market: 49 days

• Population: ~5,500

• School Districts: Lake Bluff School District 65, Lake Forest High School District 115

• Vibe: Friendly, laid-back, and artistic, with a classic small-town atmosphere.

• Highlights: A historic downtown, popular farmers market, lakeside parks, summer events, and a thriving arts scene make Lake Bluff truly special. It offers both charming vintage homes and newer construction, all close to the lake.

• Why Move Here: For buyers who want a relaxed lifestyle, a welcoming village feel, and easy access to Lake Michigan and Lake Forest amenities.

Chicago North Shore Real Estate Market Comparison (July 2025)

Town	Avg Home Price	Median Days on Market	Notable Features
Evanston	$583,500	46 days	Urban vibe, university, walkability
Wilmette	$900,000	45 days	Beaches, schools, charming downtown
Winnetka	$1,150,000	42 days	Luxury estates, lakefront, prestige
Glencoe	$1,120,000	48 days	Botanic Garden, small-town charm
Kenilworth	$1,400,000	38 days	Ultra-exclusive, historic mansions
Highland Park	$780,000	44 days	Arts, Ravinia Festival, diverse homes
Lake Forest	$749,000	46 days	Grand estates, Market Square, history
Lake Bluff	$670,000	49 days	Laid-back, artsy, lakeside village

Which North Shore Town Fits You?

• Evanston: For those who want big-city amenities, walkability, and cultural diversity.

• Wilmette: For buyers seeking the best schools, beach access, and a lively family scene.

• Winnetka: For luxury, privacy, and architectural elegance.

• Glencoe: For buyers seeking a quiet, upscale neighborhood with easy train access and gorgeous nature.

• Kenilworth: For those who desire exclusivity and a serene, legacy-oriented lifestyle.

• Highland Park: For creatives, music lovers, and anyone who values walkable neighborhoods and festivals.

• Lake Forest: For lovers of space, tranquility, and classic Midwestern beauty.

• Lake Bluff: For those wanting a relaxed, artsy village by the lake with a strong community spirit.

Chicago North Shore Real Estate Trends 2025

• Prices Are Up: North Shore home values have climbed by about 13% in the past year, with low inventory keeping demand high.

• Quick Sales: Most homes are selling in under 50 days, especially those close to the lake or within walking distance to downtowns.

• Changing Priorities: Buyers want home offices, bigger yards, and green features more than ever.

• Lakefront & Walkability Are Premium: Homes near Lake Michigan or close to vibrant main streets command the highest prices.

Ready to find your dream home on the North Shore?Every town here has a distinct personality—let’s work together to find your perfect match! Contact me for up-to-date pricing, a custom tour, or tailored advice.

Jason RosenbergChicagoland & North Shore Real Estate Expert JasonRosenbergRealEstate.com

References

• Redfin: Evanston Market, North Shore Market

• Realtor.com: Lake Forest Overview

• Home Stratosphere: Most Expensive Towns in Illinois 2025

• Wikipedia: North Shore (Chicago), Wilmette, Winnetka, Kenilworth

• John Nash Homes: Lake Forest Market

• MLS, Midwest Real Estate Data (MRED): Market trend data, July 2025

• Author’s experience as a North Shore Realtor