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.
Source: Jena Radnay @ Properties Christie’S International Real Estate via Coldwell Banker Realty
3. Chicago, IL – $21,000,000
Astor Court, a $21,000,000 estate in Chicago’s Gold Coast, spans 25,000 sq. ft. on nearly a third of an acre. Designed by Howard Van Doren Shaw, this neo-classical/Georgian Revival home features 5 bedrooms, 6 bathrooms, and a landscaped courtyard with gardens and fountains. The main residence offers over 10,000 sq. ft. of renovated living space with 13′ ceilings, Venetian plaster walls, intricate millwork, and marble fireplaces. Additional features include six rental units, totaling 45 rooms, 16 bedrooms, 17 bathrooms, and 18 fireplaces. Located steps from Michigan Avenue and the lakefront, this estate blends historic grandeur with modern luxury.
Where is Chicago?
Chicago is the third-largest city in the United States, located on the shores of Lake Michigan. It is a major center for finance, culture, and transportation, with O’Hare International Airport being one of the busiest in the world. The city is known for its iconic architecture, deep-dish pizza, and influential blues and jazz music scene. Chicago has a strong sports culture, home to teams like the Bears, Bulls, Cubs, White Sox, and Blackhawks. The city also features major landmarks such as Millennium Park, the Willis Tower, and the Museum of Science and Industry.
Foyer
A checkered marble floor leads to a red-carpeted staircase in the foyer. A large fireplace with a carved mantel sits against one wall. Ornate moldings and gold-trimmed accents line the ceiling and doorways. Antique furniture and a richly patterned rug complete the space.
Living Room
Painted ceiling beams, gilded moldings, and intricate wall detailing set a formal tone in this living room. Chandeliers hang over an assortment of upholstered seating. A grand fireplace with carved details serves as a focal point. Tall windows draped with luxurious fabric let in natural light.
Dining Room
A black dining table sits beneath a crystal chandelier in a room with large windows and high ceilings. Wall moldings and mirrored panels frame a marble fireplace. A red and blue area rug contrasts with the polished wood floor. Ornate drapery hangs from tall windows that overlook a garden.
Billiard Room
Intricate patterns cover the walls and ceiling in the billiard room. A carved wooden pool table stands at the center, surrounded by built-in bookshelves. Plush seating and detailed woodwork give the space a refined atmosphere. Large windows and elegant drapes complete the setting.
Bedroom
Hand-painted wall panels, gold accents, and draped fabric create an ornate bedroom. A grand bed with tufted upholstery and matching benches sits beneath a chandelier. Curved windows with decorative valances overlook the exterior. A custom inlaid floor design adds to the detailed craftsmanship.
Source: Natasha Motev @ Jameson Sotheby’S Intl Realty via Coldwell Banker Realty
2. Barrington Hills, IL – $22,000,000
Hidden Ponds, a $22,000,000 estate in Barrington Hills, spans 30,585 sq. ft. on 70+ private acres with rolling countryside, mature forests, two ponds, and gardens. The 8-bedroom, 14-bathroom English Country Manor features Brazilian walnut floors, limestone and vaulted ceilings, five fireplaces, multiple staircases, an elevator, and a slate roof. Highlights include a great room with a 30-ft ceiling, a chef-grade kitchen with a stone fireplace, and a first-floor primary suite with a private terrace. The lower level offers an English pub, wine cellar, billiards room, arcade, theater, guest suite, massage room, gym, and full-sized gymnasium. Outdoor amenities include a pool, spa, cabana, and a 4,400+ sq. ft. showroom building. Located near horse farms and a nature preserve, the estate combines privacy with accessibility, just 40 miles from Chicago and minutes from O’Hare Airport.
Where is Barrington Hills?
Barrington Hills is a village in the northwest suburbs of Chicago, spanning Cook, Lake, McHenry, and Kane counties. It is known for its large residential lots, equestrian properties, and extensive open spaces. The village has strict zoning laws to preserve its rural character, with many homes situated on five-acre or larger parcels. Barrington Hills is home to the Spring Creek Forest Preserve, offering trails for hiking, horseback riding, and wildlife observation. The community values conservation and maintains a quiet, low-density environment.
Living Room
Exposed wooden beams and a towering arched window define this living space with dark wood paneling. A large stone fireplace serves as a focal point, while plush seating is arranged around it. Potted trees and natural light contribute to an open feel. Polished wood floors reflect the warm glow from the fire.
Dining Room
Bold red walls and detailed crown molding frame a dining room with a long table and high-backed chairs. A fireplace with a white mantel anchors one side, with a large painting hanging above. Two chandeliers cast light across the herringbone-patterned floor. Large windows offer views of the greenery outside.
Rec Room
Exposed stone walls and wooden beams set a rustic tone in the rec room featuring a pool table at its center. Leather seating is arranged around a fireplace, creating a lounge area. A bar with high stools stands nearby, offering a place for drinks and conversation. Large windows and arched doorways connect the space to other areas.
Home Theater
Rows of reclining leather seats face a large screen in a home theater with an orange-accented ceiling. Acoustic panels line the walls, and recessed lighting illuminates the space. A raised platform ensures clear sightlines for every seat. A red curtain at the screen’s edge mimics a traditional cinema setup.
Bedroom
Sunlight streams through tall windows into a bedroom with high vaulted ceilings and white-paneled walls. A dark wooden bed sits against one wall, flanked by matching nightstands. Built-in shelves frame a central window, displaying decorative items. A sofa and a glass coffee table provide additional seating.
1. 595 Circle Ln, Lake Forest, IL 60045 – $27,500,000
This $27,500,000 Lake Forest estate spans 15,000 sq. ft. on 5.27 acres with 570 feet of Lake Michigan frontage. Completed in 2019 after four years of construction, the home includes 6 bedrooms and 9 bathrooms. Features include a protected cove beach, two boat launches, a pool, spa, and a boathouse. The estate offers 22-car garage space, with 16 underground, and an elevator connecting all four levels. Outdoor amenities include a full kitchen, multiple bluestone terraces, and three loggias. The interior boasts a Christopher Peacock kitchen, a home theater, a wine cellar, a spa room, and a billiards lounge. Smart home technology, geothermal heating, and radiant floors enhance this luxury waterfront property.
Where is Lake Forest?
Lake Forest is a city on the North Shore of Lake Michigan, about 30 miles north of Chicago. It is known for its historic estates, tree-lined streets, and strong commitment to conservation. The city is home to Lake Forest College, a private liberal arts school founded in 1857. Lake Forest has a vibrant business district, including Market Square, one of the country’s first planned shopping centers. Outdoor recreation is popular, with access to beaches, golf courses, and forest preserves.
Dining Room
A long dining table with high-backed chairs extends across a space lined with floor-to-ceiling windows. A modern chandelier hangs above, while light-colored tile flooring contrasts with dark wooden furniture. White curtains frame the doors leading outside, allowing views of the greenery beyond. A telescope stands near the windows, positioned to take in the distant landscape.
Study
Dark wood paneling and built-in bookshelves surround a fireplace in a study with arched windows and French doors. A large leather sofa and a wooden desk sit on a tiled floor, with books and framed photographs adding personal touches. A chandelier with multiple lamps hangs from the coffered ceiling, casting warm light throughout the space. Glass doors open to an outdoor area, bringing in natural light.
Bedroom
A spacious bedroom features a large upholstered bed with a matching bench at its foot. Floor-to-ceiling windows with white curtains lead to a balcony with a wrought iron railing. A wooden wardrobe and nightstands provide storage, while a chandelier hangs from a recessed ceiling. Light-colored flooring and walls create an open feel, complemented by soft lighting from bedside lamps.
Bathroom
In the bathroom, you’ll see a marble-topped soaking tub, a glass-enclosed shower, and a built-in sauna. Dual vanities with white cabinetry offer storage, and a massage table sits nearby. Stone flooring and neutral walls contribute to the spa-like atmosphere. Recessed lighting and a large window provide illumination, with a privacy shade covering the glass.
Pool
A rectangular pool sits on a stone patio overlooking a green lawn and a distant body of water. Lounge chairs and small tables are arranged along the poolside, providing seating options. A diving board extends over one end of the pool, while a low brick wall separates the area from the rest of the property. Trees and shrubs line the background, offering natural shade and privacy.
