When it comes to luxury living in the Chicago suburbs, affluent buyers seek more than just square footage or high-end finishes, they’re investing in a lifestyle. Whether it’s private golf courses, lakefront tranquility, or gated privacy, Chicagoland offers a remarkable variety of prestigious neighborhoods that cater to refined tastes and elevated expectations.
If you’re considering a luxury home purchase in the suburbs, here’s an inside look at some of the most sought-after communities where elegance and lifestyle intersect, plus what makes each one so desirable.
1. Hawthorn Woods Country Club: Resort Living in the Suburbs
Nestled in Lake County, Hawthorn Woods Country Club is more than a neighborhood, it's a private retreat. Designed around an Arnold Palmer Signature Golf Course, this gated community offers residents access to:
A full-service clubhouse with fine dining and social events
Tennis courts, fitness center, and aquatics complex
Breathtaking custom homes, many with golf course or wooded views
This is where you’ll find executive-style living with an active, family-friendly atmosphere. Whether you're entertaining on your patio overlooking the fairway or enjoying sunset walks on quiet tree-lined streets, Hawthorn Woods offers the perfect blend of luxury and leisure.
2. Lake Barrington & Barrington Hills: Space, Privacy, and Prestige
If you're seeking multi-acre estates, equestrian properties, or lakefront homes, the Barrington area is your answer.
Barrington Hills offers sprawling estates set on 5+ acre parcels with gated entries, private ponds, and room for horses. It's secluded yet just a short drive to downtown Barrington.
Lake Barrington combines luxury living with lakeside serenity, where buyers enjoy water access, wooded lots, and private docks.
This area is perfect for high-net-worth individuals who value privacy, prestige, and proximity to nature while remaining within commuting distance of the city.
3. Kildeer: Custom Homes in a Natural Setting
Known for its wooded lots, winding roads, and luxury custom homes, Kildeer appeals to buyers looking for architectural distinction and natural beauty.
Homes here often sit on 1+ acre lots, many backing to conservation land or small lakes.
There's no cookie-cutter feel, each estate tells its own story, with buyers able to customize finishes, layouts, and exteriors to match their unique lifestyle.
Despite the peaceful setting, Kildeer offers easy access to shopping, dining, and expressways, making it ideal for professionals and families alike.
4. Long Grove: Historical Charm Meets Upscale Living
Long Grove blends the timeless charm of a historic village with the appeal of luxury living. Buyers are drawn to:
Quiet neighborhoods of stately homes and manicured estates
A strong sense of community and award-winning schools
Proximity to the quaint shops, wineries, and festivals of downtown Long Grove
Long Grove is perfect for those who appreciate a slower pace, scenic beauty, and well-preserved history, all within a sophisticated, upscale environment.
5. North Shore Enclaves: Highland Park, Glencoe & Winnetka
For buyers seeking waterfront mansions, architectural pedigree, and access to the cultural pulse of Chicago, the North Shore delivers. From historic estates on Sheridan Road to modern masterpieces with Lake Michigan views, these neighborhoods offer:
Luxury with legacy, homes here often date back generations
Proximity to private clubs, elite schools, and downtown
A community of influential professionals, executives, and creatives
The North Shore is ideal for those who want it all, prestige, style, location, and amenities, in one of Chicagoland’s most iconic settings.
Why Work with a Luxury Specialist?
Buying in a high-end market demands more than MLS searches, it takes local expertise, private access, and strong negotiation. At Helen Oliveri Real Estate, we specialize in luxury transactions, offering:
Exclusive listings and pocket properties not publicly available
Deep local knowledge of zoning, development, and HOA regulations
Trusted relationships with attorneys, inspectors, lenders, and builders who specialize in luxury
We understand that buying a luxury home isn’t just a transaction, it’s a lifestyle investment. From private tours to tailored negotiations, we make your journey seamless and rewarding.
Ready to Find Your Luxury Dream Home?
Whether you're seeking a custom estate in Kildeer, a golf course gem in Hawthorn Woods, or a private lakefront sanctuary in Barrington, we’re here to help you discover what luxury living truly means in the Chicagoland suburbs.
Call or text Helen Oliveri at 847-967-0022
Explore luxury listings at helenoliveri.com