Illinois real estate is a dynamic blend of metropolitan luxury and suburban charm, with Chicago’s skyline anchoring the state’s high-end housing market.
This collection highlights four standout properties, each with its own architectural rhythm. Two are in Lake Forest, a town where old trees, formal gardens, and lakefront vistas still shape the residential landscape. One estate offers over 500 feet of private shoreline; another unfolds across 9 acres with a conservatory, guest house, and a series of secluded garden rooms.
A stately Barrington Hills manor channels English countryside tradition across more than 70 acres, while a Gold Coast landmark in Chicago reflects the city’s gilded-age elegance with 25,000 square feet of preserved craftsmanship.
Now, let’s take a look at the four of the most expensive houses currently making waves in the Prairie State.
4. Lake Forest, IL – $14,975,000
This Lake Forest estate, built in 1912, spans 11,787 square feet and includes 8 bedrooms and 10 bathrooms. Priced at $14,975,000, the property covers nearly 9 acres and features a main house, guest house, coach house, pool, pool house, conservatory, and 21 uniquely designed garden rooms. The estate has undergone major renovations and expansions since 1988 and includes elevator access to all four levels.
Where is Lake Forest?
Once a lakeside haven for Chicago’s wealthy in the 19th century, Lake Forest, Illinois, grew into a city of preserved landscapes and classic planning. It includes parts of the Lake Forest Open Lands Association, protecting over 1,000 acres of nature. Market Square, built in 1916, is often called the first planned shopping center in the country. The city offers both public and private education, including Lake Forest High School.
Sunroom
Full-height windows line this sunroom, bringing garden views inside to a space furnished with striped upholstered seating, slender chairs, and a chandelier above. Curtains are pulled to each side, revealing a patio area outside with wrought iron furniture. Polished dark flooring contrasts with the pale walls and ceiling, anchoring the room in soft light.
Media Room
Floral wallpaper wraps around this cozy room, where a large sectional sofa faces a built-in bookcase with a central TV. A doorway connects to a brighter room beyond, and framed artwork hangs neatly between corners. Neutral tones dominate the furniture and carpet, creating contrast with the detailed wall print.
Library
Bookshelves stretch floor-to-ceiling across this library, wrapping around floral-upholstered seating and a wood coffee table in the center. A writing desk and globe sit beneath framed prints, while an open doorway overlooks the chandelier-lit stairwell. The double-height room uses warm tones and traditional furniture to create a compact yet layered reading space.
Conservatory
Glass walls and a vaulted ceiling define the greenhouse, which holds sculpted topiary trees, ferns, and potted plants across a brick floor. Wicker seating and iron tables provide places to rest beneath the natural light. Dark green framing and open doors connect the space directly to the surrounding garden.
Aerial View
Surrounded by manicured lawns and dense tree cover, the property sits near a large body of water with a curved driveway leading to a symmetrical brick motor court. Multiple chimneys, dormers, and ivy-covered walls give structure to the sprawling main house. Defined lawn stripes and hedges divide the landscape into formal garden spaces and open grassy areas.
Source: Ann Lyon @ @Properties Christie’S International Real Estate via Coldwell Banker Realty
3. Chicago, IL – $21,000,000
Located in Chicago’s Gold Coast and built in 1914, this estate offers 25,000 square feet of living space with 5 bedrooms and 6 bathrooms. Priced at $21,000,000, it occupies nearly one-third of an acre and includes a main residence and six additional rental units for a total of 45 rooms. The property spans 80 feet across Astor Street and features a central courtyard, original architectural details, and two parking spaces with potential for expansion.
Where is Chicago’s Gold Coast Neighborhood?
Chicago’s Gold Coast neighborhood stretches along Lake Michigan, just north of downtown and the Magnificent Mile. It’s known for its historic mansions, tree-lined streets, and proximity to Oak Street Beach. The area blends quiet residential charm with walkable access to high-end boutiques, dining, and landmark architecture.
Living Room
Gold trim outlines the walls and ceiling beams of this formal living room, which features multiple seating areas and large crystal chandeliers. Patterned armchairs and classic sofas cluster atop layered rugs, anchored by candelabras and framed mirrors. The room connects to others through wide gold-framed openings and borders a windowed alcove at one end.
Dining Room
Ornate plasterwork and mirrored fireplace define the dining room, where a black dining table and wood chairs sit atop a red oriental rug. Full-length windows and carved drapes line one side, opening up to the garden views beyond. Crystal chandeliers and brass sconces complement the fireplace and traditional millwork around the perimeter.
Office
Gold trim and green-paneled walls frame this office, where a black desk with brass latticework sits beside a velvet chair and carved armchair. Twin chandeliers hang from the ceiling, while windows bring in natural light over floral drapes and potted plants. A fireplace anchors one wall with symmetrical mirrors, flanked by deep purple lounge seating and a low table.
Billiard Room
Painted in vibrant blue and red, the ceiling of this library and billiard room contrasts with wood-paneled bookshelves filled with volumes. A carved pool table stands in the center, surrounded by antique chairs, reading lamps, and heavy window treatments. Open doorways connect the space to the formal living room and reveal matching decorative themes throughout.
Courtyard
Brick and wrought iron define this inner courtyard enclosed by the home’s multi-story walls, with curved stairs leading to a second-level entry. A stone-paved path winds between garden beds, water features, and a dense mix of tropical and flowering plants. Upper floors feature black-framed windows, blending historic structure with lush landscape elements.
Source: Natasha Motev @ Jameson Sotheby’S Intl Realty via Coldwell Banker Realty
2. Barrington Hills, IL – $22,000,000
On over 70 acres in Barrington Hills, this 30,585 square feet English Country Manor estate offers 8 bedrooms and 14 bathrooms. Built in 2004, the residence includes a full-sized gymnasium, two ponds, a pool with cabana, and a separate 4,400 square feet showroom building. Listed at $22,000,000, the gated property also features a 6-car attached garage, elevator, multiple entertaining spaces, and a 9,000 square feet lower level with an English pub, wine cellar, and movie theater.
Where is Barrington Hills?
Barrington Hills, Illinois, spans across four counties northwest of Chicago and is known for its large residential lots and equestrian-friendly zoning. The area blends rural character with forest preserves, trails, and private horse farms. It operates under a village government and enforces five-acre minimum zoning for homes. Barrington Hills shares community ties with the nearby Village of Barrington.
Great Room
Cathedral ceilings with exposed trusses rise above the great room, where a carved stone fireplace and wood-paneled walls add scale and warmth. Potted trees frame a large arched window wall, letting light pour into the seating areas split across the polished wood floor. Sofas and a marble-topped coffee table gather along a decorative rug to the left of the fireplace.
Dining Room
Red walls wrap around this formal dining room, where a long black dining table and high-backed chairs sit beneath two iron chandeliers. A fireplace and decorative mantle add a focal point on one end, crowned by a large framed artwork. Herringbone hardwood floors continue through arched openings into the adjoining hallway.
Bedroom
Natural light spills into this primary bedroom through tall mullioned windows and skylights cut into the vaulted ceiling. A dark wood bed and matching nightstands sit against a paneled wall, while a pale carpet extends across the entire room. Built-in shelves cover the far wall, balancing display space with cabinetry under a large central window.
Bathroom
Arched windows and cream tile floors define the bathroom, where a soaking tub is set beneath the window on a raised surround with wooden paneling. Twin vanities are built into a symmetrical cabinet wall with recessed lighting and mirrors. Natural tones dominate the room, emphasized by the warm wood cabinetry and pale wall finish.
Pool Area
Stone hot tub anchors the foreground of this backyard, positioned beside a rectangular pool and surrounded by loungers, umbrellas, and outdoor tables. A peaked pool house structure opens into shaded seating, blending with the larger Tudor-style home in the background. Manicured lawn and hedges line the space, offering a clean visual border to the hardscaping.
1. Lake Forest, IL – $27,500,000
Commanding over 5.27 acres along Lake Michigan with 570 feet of private shoreline, this Lake Forest estate delivers 15,000 square feet of living space. Completed in 2019, the home includes 6 bedrooms, 9 bathrooms, and garage capacity for 22 vehicles. Listed at $27,500,000, the property also features a pool, spa, boathouse, and a range of luxury amenities across four finished levels.
Where is Lake Forest?
Lake Forest, Illinois, sits along the western shore of Lake Michigan, about 30 miles north of Chicago. The city is known for its historic estates, preserved woodlands, and strong connection to early American architecture. It is home to Lake Forest College and several nature preserves, including the Middlefork Savanna. The downtown area features a mix of small shops, dining, and a commuter rail station.
Lounge
Neutral walls and a coffered ceiling define this formal sitting room, where two white armchairs and a blue velvet settee gather around a central coffee table. A pop-art painting leans against one wall near the staircase, while wide openings reveal a dining room beyond. Floor-to-ceiling curtains and dark wood floors give the room a refined yet open character.
Kitchen and Breakfast Nook
Exposed wooden beams stretch across the ceiling of this kitchen, where a blue range and white cabinetry are paired with a large island featuring a polished stone countertop. Pendant lights hang above the island, facing an open-concept dining space with script-patterned chairs and curved window frames. French doors and expansive windows bring in natural light from the surrounding patio.
Home Office
Dark wood paneling encloses this library, where arched windows, built-in shelves, and a roaring fireplace surround a central workspace filled with stacked books. A tan leather sofa anchors the seating area, flanked by lamps and a side table near the bookshelves. Overhead, a chandelier hangs from a coffered ceiling, completing the traditional study aesthetic.
Spa Bathroom
Stone flooring runs through this spa-like bathroom, where a glass-enclosed steam shower and a cedar sauna sit beside a marble bench and vanity area. Twin sinks are installed below a large mirror, and recessed ceiling lights brighten the space evenly. A treatment table lies in the foreground, indicating space for wellness routines or massages.
Pool Area
Rectangular in shape, the backyard pool sits in the center of a stone-paved patio bordered by trees and open lawn stretching toward a water view. Yellow lounge chairs and black metal tables line one side, while a diving board extends from the other. A brick structure and steps rise at the far end, marking the transition between the house and the pool terrace.
Source: Ann Lyon @ @Properties Christie’S International Real Estate via Coldwell Banker Realty
