With its stunning lakefront views, historical charm, and proximity to Chicago, Highland Park, IL, has long been a sought-after suburb for luxury living. Known for its affluent residents and breathtaking estates, the city boasts some of the most exclusive and priciest neighborhoods in the North Shore area. Whether you’re looking to purchase a home, invest in real estate, or simply curious about the area’s luxurious enclaves, this guide will explore the most expensive neighborhoods in Highland Park, offering insights into their unique features and allure.

Why Highland Park Is a Hub for Luxury Living 

Highland Park has earned its reputation as a premier destination for affluent buyers thanks to its strategic location along Lake Michigan, highly rated schools, and vibrant community. Residents enjoy a blend of suburban tranquility and access to urban amenities like fine dining, high-end shopping, and cultural attractions. The city’s well-maintained parks, beaches, and recreational spaces further contribute to its appeal.

But what truly sets Highland Park apart are its neighborhoods, boasting stately mansions, architectural masterpieces, and modern estates built with luxury in mind. Let’s take a closer look at the most exclusive areas that dominate the real estate market.

1. Braeside 

The one and only Braeside is one of Highland Park’s most prestigious neighborhoods, with a rich history and a close-knit community feel. Located in the southern part of the city, the area is defined by tree-lined streets, sprawling lots, and an array of architectural styles, from Tudor to Georgian and mid-century modern homes.

Key Features of Braeside:

• Proximity to Ravinia Festival: This neighborhood borders the Ravinia Festival grounds, one of Highland Park’s cultural highlights, providing music and arts enthusiasts with unparalleled access to world-class performances.
• Top-tier Schools: Home buyers with young kids are drawn to this area for its highly regarded public schools, including Ravinia Elementary School, which has received accolades for its academic excellence.
• Average Home Prices: Expect home prices to range from $1.2 million to $3 million for larger estates on oversized lots.

2. Highland Park Estates 

True to its name, Highland Park Estates offers some of the most luxurious homes in the city. Situated in central Highland Park, this area combines convenience with exclusivity, making it a favorite for business professionals and families alike.

Key Features of Highland Park Estates:

• Luxury Homes: The neighborhood is dotted with custom-built mansions featuring amenities like home theaters, wine cellars, and outdoor pools.
• Shopping and Dining: Its central location means residents are minutes away from popular spots like Port Clinton Square and other downtown Highland Park attractions.
• Average Home Prices: Homes in this area often start at $1.5 million and can exceed $5 million for newly constructed estates.

3. Sheridan Road Corridor 

Sheridan Road is synonymous with luxury in the North Shore area, and the stretch that runs through Highland Park is no exception. This corridor offers some of the most exclusive homes, many of which are perched on Lake Michigan’s shores.

Key Features of Sheridan Road Corridor:

• Lakefront Properties: Homes with private beach access and panoramic lake views are common here, making it a prime location for water lovers.
• Architectural Significance: Several estates were designed by renowned architects, adding historical and artistic value to the neighborhood.
• Average Home Prices: Lakefront properties can range from $4 million to over $10 million, depending on the size and modernity of the estate.

4. Hybernia 

The Hybernia neighborhood brings a unique twist to Highland Park’s luxury market by combining upscale living with eco-conscious design. This neighborhood in the western part of the city features homes surrounded by natural beauty, including ponds, wetlands, and lush greenery.

Key Features of Hybernia:

• Environmental Design: Many homes here incorporate sustainable construction practices and blend seamlessly with the natural landscape.
• Private Community Atmosphere: Hybernia is a gated neighborhood, which adds to its exclusivity and ensures privacy for its residents.
• Average Home Prices: Properties range from $1 million to $3 million, with some exceeding these figures due to unique design elements.

5. East Highland Park 

This neighborhood has gained attention for its vibrant blend of historical charm and contemporary luxury. Located east of Green Bay Road, East Highland Park offers proximity to the lake as well as the city’s bustling downtown.

Key Features of East Highland Park:

• Historic Properties: Streets are lined with elegant estates, some dating back to the early 1900s, alongside newer construction.
• Walking Distance to Lakefront Parks: Residents can easily access Rosewood Beach and other scenic waterfront areas.
• Average Home Prices: Properties here typically range from $800k for smaller homes to $2.5 million for updated, larger estates.

6. Ravinia 

Ravinia is a favorite among Highland Park home buyers who value both luxury and a sense of community. Known for its proximity to the Ravinia Festival and charming village-like atmosphere, this neighborhood is as quaint as it is exclusive.

Key Features of Ravinia:

• Artistic & Musical Heritage: Hosting the country’s oldest outdoor music festival, the neighborhood pulses with creativity and culture.
• Charming Homes: Ravinia boasts a mix of quaint cottages, renovated historic homes, and modern builds that cater to various tastes.
• Average Home Prices: Homes in Ravinia range from $700k to $2 million, with occasional lakefront gems exceeding $3 million.

7. Deere Park 

Deere Park stands out as one of Highland Park’s most picturesque neighborhoods, offering a tranquil setting with a strong sense of privacy. Nestled along the shores of Lake Michigan, this area is renowned for its stunning natural beauty and charming architectural designs. Residents in Deere Park enjoy the peaceful ambiance of living near expansive wooded areas and beachfront properties, making it a haven for those seeking respite from the bustle of city life.

Key Features of Deere Park:

• Lakefront Access: The neighborhood’s proximity to Lake Michigan allows residents to experience the serene beauty of the lake, with private access points and trails providing opportunities for walking, biking, and waterside relaxation.
• Spacious Estates: Homes here are typically large and well-appointed, with sprawling grounds that offer both luxury and seclusion. Many residences include features such as private tennis courts, gardens, and long driveways.
• Average Home Prices: Due to its desirable location and unique attributes, properties in Deere Park command premium prices, generally ranging from $2 million to $7 million, with some exclusive estates exceeding these figures based on size and amenities.

8. Fort Sheridan

Fort Sheridan offers a unique blend of history, luxury, and stunning natural landscapes, making it an attractive neighborhood within Highland Park. Located along the Lake Michigan shoreline, this area is characterized by its meticulously preserved former military base facilities and sprawling residential properties that combine historical significance with modern comfort.

Key Features of Fort Sheridan:

• Historic Charm: The neighborhood is rich in history, featuring preserved landmarks such as the iconic Tower and a variety of homes that were once officer’s quarters. These structures are now beautifully restored and offer a glimpse into the past.
• Nature and Recreation: With access to the Fort Sheridan Forest Preserve, residents enjoy outdoor activities ranging from hiking and bird watching to exploring the scenic trails that meander through the area’s prairies and woodlands.
• Community and Lifestyle: Fort Sheridan fosters a close-knit community atmosphere, with regular events and gatherings that enhance neighborly connections. Its proximity to both the beach and natural areas provides a serene lifestyle for those seeking tranquility.
• Average Home Prices: Properties in Fort Sheridan vary widely, with historical homes and modern residences ranging from $700k to $3 million, depending on location, size, and historical significance.

9. High Ridge 

High Ridge is a prestigious enclave known for its elevated views and distinguished properties. Nestled within the natural beauty of the surrounding landscape, this neighborhood offers an unparalleled sense of serenity and exclusivity in Highland Park. With its gently rolling hills and beautifully manicured landscapes, residents of the High Ridge neighborhood enjoy both privacy and convenience in a truly picturesque setting.

Key Features of High Ridge:

• Scenic Views: The elevated location affords panoramic views of the surrounding area, enhancing the aesthetic appeal of this distinguished community. Residents can relax in their homes while taking in breathtaking sunsets and lush vistas.
• Upscale Living: Homes in High Ridge are known for their luxurious designs and high-end features, catering to those who seek exceptional quality and design. Many properties include sophisticated interiors, expansive living spaces, and premium amenities.
• Community Amenities: The neighborhood encourages a tight-knit community vibe with amenities such as private parks, sports courts, and social clubs. Events hosted here foster a sense of belonging and engagement among residents.
• Average Home Prices: Reflecting its luxury market position, properties in High Ridge typically range from $1.5 million to over $5 million, depending on the size and exclusivity of the estate. Some homes may exceed these values due to their superb location and architectural significance.

What Drives Prices in These Neighborhoods? 

The premium price tags associated with Highland Park’s neighborhoods are justified by several factors, including access to pristine lakefronts, historical significance, top-tier schools, and unparalleled amenities. Additionally, proximity to Chicago and the area’s low crime rate attract affluent buyers seeking both security and convenience.

Architectural significance also contributes to these neighborhoods’ exclusivity. Many homes are custom-built, designed by famous architects, or renovated estates with a bespoke charm that’s hard to replicate elsewhere.

Final Thoughts on Highland Park’s Most Exclusive Neighborhoods 

Highland Park continues to set the standard for luxurious suburban living with its blend of cultural vibrancy, natural beauty, and family-friendly atmosphere. Whether you’re drawn to a lakefront property along Sheridan Road, the sustainable splendor of Hybernia, or the musical legacy of Ravinia, there’s no shortage of incredible neighborhoods to explore in Highland Park.

If you’re considering a move, Highland Park’s real estate market offers timeless elegance paired with modern amenities—a winning combination for discerning buyers.

Looking to make Highland Park your next home? Our team of local realtors specializes in luxury properties and can guide you through the process every step of the way. Get in touch today to learn more about your dream neighborhood!