If walls could talk, these Illinois mansions would have entire libraries of stories to tell—tales of Gilded Age opulence, architectural ambition, and the grand traditions of the state’s elite. From stately residences in Chicago’s most distinguished neighborhoods to a sprawling Evanston estate, each of these historic homes is a masterclass in craftsmanship, where intricate moldings, towering fireplaces, and storied pasts collide with modern luxury.
On Drexel Boulevard, a 7,100-square-foot beauty once designed for a Brunswick Company magnate offers barrel-domed ceilings and a rooftop deck with skyline views. In Wicker Park, an 1889 masterpiece balances preserved Victorian charm with contemporary updates fit for the most discerning homeowner. And in Evanston, an 1874 mansion sprawls across a lush 28,000-square-foot lot, where Corinthian columns and marble fireplaces transport you back to an era when grandeur knew no bounds.
These homes don’t just stand—they reign, proving that true elegance is indeed timeless.
1. 7,100 Sq. Ft. Drexel Boulevard Estate
Listed for $1,499,000, this 7,100 sq ft, five-bedroom, six-and-a-half-bathroom estate on Drexel Boulevard was originally designed in 1900 by architect Horatio Wilson for Benjamin Bensinger of the Brunswick Corporation. The three-story home retains original architectural details, including grand fireplaces, barrel-domed plaster ceilings, and hardwood flooring, while featuring a fully redesigned modern interior. The property includes a coach house, a four-car garage with additional living or office space, a finished basement with a wet bar and wine cellar, and a rooftop deck with panoramic views.
Where is Chicago, IL?
Chicago, IL, is the third-largest city in the United States, located in northeastern Illinois along the southwestern shore of Lake Michigan. It is approximately 280 miles southwest of Detroit, 180 miles northwest of Indianapolis, and 90 miles north of the state capital, Springfield. As a major transportation hub, Chicago is about 715 miles from New York City and 2,000 miles from Los Angeles, making it a central point for travel and commerce in the Midwest.
Foyer
A curved vaulted ceiling with intricate detailing adds architectural character to the hallway. A dark stone fireplace with a wooden mantel provides warmth and contrast against the light wood flooring. A grand staircase with white paneling and black iron railings leads to the upper level.
Living Room
Curved seating arrangement with tufted sofas surrounds a glass coffee table on a plush area rug. A sleek fireplace with a dark accent wall adds warmth and contrast to the neutral color palette. Large bay windows bring in natural light and offer views of the surrounding neighborhood.
Dining Room
Glass dining table with sleek metallic chairs sits beneath an intricate ceiling with sculpted detailing. Large windows bring in natural light, complementing the neutral tones and wood flooring. A black sideboard with gold accents and abstract artwork adds a stylish contrast.
Bedroom
A curved wall with large windows, bringing in abundant natural light and outdoor views. The room is designed with a soft neutral palette, complemented by a dark accent wall with a built-in fireplace and a decorative mirror. A plush bed with textured bedding and colorful accent pillows adds warmth, while a modern ceiling fan and sleek furnishings enhance the contemporary aesthetic.
Source: Coldwell Banker
2. Renovated 1889 Wicker Park Home
Listed for $2,499,000, this 4,605 sq ft, five-bedroom, four-and-a-half-bathroom home in Wicker Park was originally built in 1889 and underwent a full renovation in 2018. Historic details such as 10’ ceilings, oversized windows, original woodwork, and four wood-burning fireplaces have been preserved while integrating modern updates, including a chef’s kitchen with a marble island, a folding glass door to the back patio, and an expanded lower level with high ceilings. The property features a primary suite with a walk-in closet and marble bath, a basement with a media room and bar, and potential for a rooftop deck over the garage.
Where is Wicker Park in Chicago?
Wicker Park is a vibrant neighborhood located on Chicago’s West Side, roughly four miles northwest of downtown, bordered by Bucktown to the north, Ukrainian Village to the south, and Humboldt Park to the west. Centered around the bustling intersection of North, Damen, and Milwaukee Avenues, the area is well-connected by public transit, including the CTA Blue Line at Damen Station, providing quick access to downtown and O’Hare International Airport. Known for its historic architecture, trendy boutiques, and dynamic arts and dining scene, Wicker Park blends old Chicago charm with a hip, modern atmosphere.
Living Room
White walls and ceiling contrast with dark furniture and a wooden mantel over the fireplace. A large blush-colored sofa and two cream armchairs surround a rectangular black coffee table. Natural light enters through large windows, partially covered by long curtains. A chandelier with exposed bulbs hangs from the ceiling, complementing the warm lighting from the lamps and fireplace.
Dining Room
Patterned wallpaper and dark wood trim contrast with a light-colored ceiling and area rug. A rectangular wooden dining table with six woven-back chairs sits under a black chandelier with candle-style bulbs. Large windows with floor-length curtains allow natural light to enter the space.
Bedroom
A dark wood fireplace with a marble surround is positioned between two black dressers. A chandelier with candle-style bulbs hangs above a bed with white linens and a gray throw. Large windows with floor-length curtains provide a view of greenery outside.
Bathroom
White freestanding bathtub is positioned in front of large windows with fabric Roman shades. A double vanity with a marble countertop and dark wood cabinetry spans the wall, accompanied by wall-mounted sconces and mirrors. A glass-enclosed shower is situated to the left, and a chandelier hangs from the ceiling.
Source: Coldwell Banker
3. 1874 Evanston Mansion
Listed for $1,579,000, the Charles J. Gilbert House is a 7,500 sq ft, seven-bedroom, five-bathroom Second Empire Victorian estate in Evanston, originally built in 1874 for a former congressman. The home features historic architectural details, including a mansard roof, Corinthian column portico, imported Italian marble fireplaces, hand-carved plaster medallions, and original woodwork. Situated on a 28,000 sq ft lot, the property includes a large landscaped yard, a covered porch, two in-law apartments, a ballroom, and is within walking distance to downtown Evanston, public transportation, Northwestern University, and Lake Michigan.
Where is Evanston, IL?
Evanston, IL is a suburban city located 12 miles north of downtown Chicago, 95 miles south of Milwaukee, and 280 miles west of Detroit, along the shores of Lake Michigan in Cook County. It is home to Northwestern University and is known for its historic architecture, cultural attractions, and mix of urban and suburban living. Evanston offers easy access to Chicago via Metra and the CTA “L” train, along with numerous shopping, dining, and recreational options, including lakefront parks and beaches.
Living Room
A large white sectional sofa with patterned upholstery is positioned around a glass coffee table on a black and white area rug. Built-in wooden display cabinets flank the large windows, which provide a view of the lush greenery outside. A crystal chandelier hangs from the ceiling, complementing the wood flooring and intricate wall paneling.
Dining Room
Glass-top dining table is surrounded by six white cane-back chairs on a dark patterned rug. A crystal chandelier hangs from the ceiling, illuminating the white paneled walls and decorative moldings. A stained glass window and an ornate black and gold cabinet add to the room’s refined aesthetic.
Kitchen
White cabinets with black granite countertops line both sides of the narrow kitchen. A gas cooktop and built-in microwave are installed along one wall, while a stainless steel sink and dishwasher sit under a large window. A doorway leads to an adjacent space with additional storage and a breakfast nook.
Porch
White Corinthian columns support the covered porch, which has decorative railings and wood flooring. Green wicker chairs and a glass-top table provide seating near the black-framed windows. Lush greenery surrounds the space, creating a semi-private outdoor area.
Source: Coldwell Banker
