Find the Chicago home that speaks to you

Magnificent Masonry Estate with Private Basketball Court

This extraordinary 8,000-square-foot custom residence on prestigious North Park Avenue represents the pinnacle of luxury living in Chicago's coveted Old Town/Gold Coast neighborhood. Constructed from exquisite masonry brick and limestone, the home features seven bedrooms, a professional indoor basketball court, and a distinctive turret tower offering panoramic city views. From the chef's kitchen with Wolf appliances to the rooftop deck and geothermal heating, every detail reflects meticulous craftsmanship and thoughtful design.

Featured by Chaz Walters

Georgian Masterpiece with Hollywood Heritage and Modern Luxury

This magnificent 9,126-square-foot Georgian estate, built in 1921, seamlessly blends timeless architectural elegance with contemporary luxury across three thoughtfully designed levels. Featuring five bedrooms, six full bathrooms, and extraordinary entertaining spaces including a home theater, indoor basketball court, and multiple fireplaces, this iconic property offers unparalleled sophistication on over half an acre of meticulously maintained grounds.

Featured by Kevin McCalister

Lincoln Park Multigenerational Estate with Private Coach House

This extraordinary Lincoln Park estate redefines luxury family living on an exceptional double lot. Behind original wrought iron gates, the property features a meticulously renovated main residence connected to a private coach house above a five-car garage, creating unprecedented opportunities for multigenerational living. With six bedrooms, sophisticated entertaining spaces, and a wine cellar, this home has been the backdrop for countless family celebrations across its sun-drenched terraced grounds.

Featured by Emily Sachs Wong

Architectural Penthouse Commanding Chicago's Entire 64th Floor

An unparalleled achievement in residential design, this 8,500-square-foot penthouse occupies the entire 64th floor of the prestigious Park Tower, offering 360-degree views of Chicago's magnificent skyline. Meticulously crafted by Marvin Herman & Associates and interior designer Mitchell Turnbough, this extraordinary residence features hand-plastered walls, custom anegre wood paneling, and a dramatic salmon-pink velvet grand salon with polished black granite floors that create an atmosphere of refined luxury and architectural distinction.

Featured by Carrie McCormick

New-Construction North Shore Estate on Private Highland Park Acre

This exceptional new-construction residence commands nearly an acre in Highland Park's prestigious High Ridge neighborhood, offering 6,600 square feet of sophisticated living across three meticulously designed levels. Positioned on a private cul-de-sac, the home seamlessly blends contemporary luxury with timeless elegance, featuring premium Thermador appliances, custom millwork, and an entertainer's paradise lower level complete with wet bar and fitness facility.

Featured by Brandy Isaac

Historic Gold Coast Mansion by Renowned Architects Cobb & Frost

The Thompson House stands as one of Chicago's most significant architectural treasures, designed in 1888 by the legendary firm Cobb & Frost. This nationally registered Historic Landmark spans 13,400 square feet of meticulously restored grandeur, where original 19th-century craftsmanship meets sophisticated modern amenities. From hand-carved Italian marble fireplaces to Honduras mahogany millwork throughout, every detail reflects uncompromising artistry and timeless elegance.

Featured by Millie Rosenbloom

Prestigious Nantucket Estate on East Glenview's Pleasant Lane

This meticulously updated Nantucket-style estate commands nearly half an acre on coveted Pleasant Lane, surrounded by multi-million-dollar properties in East Glenview's most prestigious enclave. The sprawling residence seamlessly blends timeless coastal architecture with sophisticated modern amenities, featuring rich hardwood floors, soaring vaulted ceilings, and walls of windows that frame the resort-style backyard oasis with its stunning in-ground pool.

Featured by Anne DuBray

Extraordinary Duplex Estate Above Four Seasons Chicago

Perched atop the iconic Four Seasons Hotel and 900 North Michigan Avenue, this magnificent 6,700+ square foot duplex represents the pinnacle of Chicago luxury living. With soaring 20-foot ceilings, custom millwork throughout, and panoramic views spanning Lake Michigan to the city's architectural icons, this residence seamlessly blends artisanal craftsmanship with modern sophistication. The thoughtfully designed layout includes three bedrooms, multiple office suites, a private theater, and wine cellar, while residents enjoy exclusive access to world-class Four Seasons amenities and services.

Featured by Sophia Klopas

Tudor Grandeur on Ten Private Acres in Lake Forest

This meticulously restored Tudor estate commands nearly ten acres of award-winning gardens, bordered by pristine prairie preserve in prestigious Lake Forest. The century-old home showcases original walnut paneling, soaring ceilings, and masterful craftsmanship throughout nearly 6,000 square feet of refined living space. An extraordinary outdoor entertainment complex features a resort-style pool, complete outdoor kitchen, and multiple gathering areas for thirty guests.

Featured by Donna Mancuso