Skyscraping penthouses, lakefront mansions, and palatial estates paint Illinois’ real estate market as a canvas of luxury, where old-world elegance meets cutting-edge design. The state’s blend of historic charm and modern extravagance attracts elite buyers seeking world-class architecture, stunning lakefront views, and unparalleled amenities. Whether it’s a Gold Coast mansion dripping in old-money elegance or a contemporary retreat with cutting-edge design, Illinois’ most luxurious homes redefine sophistication.
Now, let’s take a look at the five most expensive houses in the Land of Lincoln, where prestige comes with a hefty price tag.
5. Chicago, IL – $6,250,000
A 7,252 sq. ft. single-family home, listed for $6,250,000, sits on an extra-wide lot at Sedgwick and Dickens. Featuring 4 bedrooms and 7 bathrooms, the residence includes custom finishes, slab marble and hardwood floors, an elevator to all levels, and three powder rooms for convenience. The main level offers spacious formal areas, a library/family room with yard access, and a sun-filled kitchen and dining space. The primary suite includes a dressing room and a marble bath, while the top-floor atrium sunroom opens to a full roof deck with a fireplace. An attached 2-car garage and driveway complete the home, located near top schools.
Where is Chicago?
Chicago is a major Midwestern city known for its diverse neighborhoods and deep cultural influence. It played a key role in the development of modern architecture, with pioneers like Louis Sullivan and Frank Lloyd Wright shaping its skyline. The city is a transportation hub, with Union Station, major highways, and a vast public transit system, including the “L” train. Chicago is home to world-class institutions like the Art Institute of Chicago and the University of Chicago. It also has a rich history in politics, being the hometown of several U.S. presidents, including Barack Obama.
Kitchen
Sleek countertops and warm-toned cabinetry define the kitchen’s modern design. A large island with built-in seating offers additional prep space and casual dining. Stainless steel appliances, including a professional-grade range, add to the functionality. Large windows bring in natural light, complementing the bright and open layout.
Dining Room
Hand-painted murals depicting exotic landscapes wrap around the dining room walls. A long wooden table with matching chairs sits at the center, framed by decorative vases and sculptures. A chandelier hangs above, providing lighting that highlights the detailed furnishings. The room’s blend of artwork and classic furniture creates a formal yet inviting atmosphere.
Bedroom
Large windows framed by draped curtains brighten the spacious bedroom. A sitting area with a plush sofa and glass coffee table creates a cozy retreat. A decorative rug extends across the hardwood floor, connecting the sleeping and lounging spaces. Soft tones and elegant furnishings give the room a timeless feel.
Bathroom
Curved walls and mirrored panels shape the bathroom’s distinctive design. A walk-in shower with multiple showerheads provides a spa-like experience. A black stone countertop contrasts with the light-colored flooring and walls. An open doorway leads to a dressing area with built-in storage.
Sunroom
Glass ceilings and walls enclose a sunroom filled with natural light. A round glass window set into the checkered floor adds a striking feature. Sliding doors open to a terrace with outdoor seating and decorative lanterns. Views of greenery and city buildings create a balance between nature and urban surroundings.
Source: Emily Sachs Wong @ Properties Christie’S International Real Estate via Coldwell Banker Realty
4. Winnetka, IL – $11,999,900
Valued at $11,999,900, this lakefront estate in Winnetka spans 15,784 sq. ft. on 1.3 acres with 7 bedrooms and 8 bathrooms. Designed across four floors, the home features a boutique-level pool and spa overlooking a 100-ft-wide sandy beach, tiered patios, multiple garages, and an elevator. Architectural highlights include mahogany floors, Tiffany glass doors, a Chagall-inspired mosaic ceiling, and floor-to-ceiling windows with lake views. The gourmet kitchen opens to a great room and outdoor terraces with an alfresco kitchen. The lower level includes a theater, gym, steam shower, golf simulator, and bar with direct access to the pool and beach. Located near town, trains, and Village Green, this estate offers prime lakefront living.
Where is Winnetka?
Winnetka is a village on Chicago’s North Shore, known for its historic homes, tree-lined streets, and lakefront access. It has a strong public school system, including New Trier High School, one of the top-ranked schools in Illinois. The village features a walkable downtown with shops, restaurants, and the historic Winnetka Community House. Winnetka’s beaches and parks along Lake Michigan provide outdoor recreation for residents. The community has been used as a filming location for several well-known movies, including Home Alone .
Living Room
A spacious living area connects to an open kitchen, with wooden ceiling beams adding architectural interest. Multiple seating arrangements include sofas, armchairs, and an ottoman. A large rug covers the tiled floor, bringing warmth to the space. French doors along one wall open to an outdoor setting.
Dining Room
Long wooden tables and high-backed upholstered chairs define the formal dining room. A chandelier with crystal accents hangs from a curved ceiling, while wall sconces provide additional lighting. Large windows allow natural light to enter, complementing the neutral color scheme. A framed artwork and decorative details add refinement to the setting.
Study / Library
Wood-paneled walls frame a library lined with built-in bookshelves filled with books and decorative items. A fireplace with a marble surround acts as the focal point, with two upholstered chairs placed in front. A stained-glass lamp adds color to the room’s design. The detailed woodwork and rich tones give the space a classic study atmosphere.
Home Theater
Rows of black leather recliners face a large projector screen in the home theater. Patterned panels and geometric lighting fixtures line the walls, enhancing the cinematic atmosphere. A coffered ceiling with recessed lighting creates depth and dimension. The design reflects the feel of a traditional movie theater.
Bathroom
Curved windows surround a built-in soaking tub, allowing natural light to fill the space. A chandelier hangs above, adding a decorative element. Neutral tones and subtle geometric patterns on the tub’s base create a clean look. The view outside showcases trees, enhancing the open feel of the room…