Chicago’s older houses aren’t always obvious. They don’t announce themselves with velvet ropes or dramatic plaques. You pass them on quiet streets—maybe near the lake in Lincoln Park, maybe tucked behind trees in Hyde Park—and only when you look twice do the details register. Carved stonework above the doorway. Leaded glass holding a pattern from another decade. Brick that has outlasted more than a few generations of owners.
These five homes aren’t museum pieces. They’ve been updated, lived in, changed. What makes them historic isn’t just when they were built, but how they’ve stayed useful. They reflect a version of Chicago that values craft, space, and long timelines. In the Gold Coast, one former greystone has a rooftop built for summer evenings. In Old Town, a converted firehouse holds onto its structure while offering the comforts of a full compound. These houses are reminders that architecture can evolve without giving up its sense of place.
Walk through them and you’ll see practical choices alongside preserved charm. Solar panels over slate roofs. Heated floors below century-old molding. The history is in the details, but so is the future.
1. Arts & Crafts Gem
Built by noted local architect Thomas McCall, this 3,000 square foot Arts & Crafts home in Hyde Park features 4 bedrooms and 4 bathrooms. The residence, constructed in the early 20th century, showcases original woodwork, stained-glass windows, and other period details alongside modern upgrades like solar energy and an electric vehicle charger. Listed at $1,450,000, it sits on a spacious lot with a two-car garage and offers proximity to the University of Chicago.
Where is the Hyde Park Neighborhood?
Hyde Park is a South Side neighborhood home to the University of Chicago and the Museum of Science and Industry. It borders Lake Michigan and includes Jackson Park, designed by Frederick Law Olmsted. Barack Obama lived here before his presidency. The area blends residential streets with academic and cultural institutions.
Living Room
Leaded glass doors open into a living room centered around a tiled fireplace with a lit fire. In the middle of the room, a large bay window frames a wooden seating set, accompanied by a patterned rug and warm-toned trim. To the right side, vintage stereo equipment and a framed print add detail near the windowed wall.
Kitchen
Natural wood cabinets line the kitchen, paired with a tiled backsplash and large window over the sink that faces a residential view. A wooden door with decorative wrought iron detail opens to the outside near a slim table with stools. A modern stainless steel refrigerator and glass-fronted cabinets balance older charm with functionality.
Dining Room
In the dining room, green wallpaper with a repeating motif wraps around wood-paneled wainscoting and built-in cabinetry. A long oval table occupies the center, surrounded by classic chairs and lit by a geometric pendant light. Two wide doorways create a connection to both the living room and an adjacent seating area.
Study / Home Library
Floor-to-ceiling shelves fill the walls of the room, holding books stacked tightly in every direction. A leather chair with an ottoman, wooden desk, and low daybed with cushions are arranged to take advantage of the sunlight from the wide row of windows. Rugs and small sculptures add texture to the personal and functional space.
Bedroom
A chandelier hangs at the center of the bedroom ceiling, positioned above a wooden bed with green bedding. Dressers, an armoire, and framed prints define the layout, which includes symmetrical windows on either side of the bed. A small door opens into a connected space or closet just off to the left.
Source: Susan O’Connor @ Berkshire Hathaway HomeServices Chicago via Coldwell Banker Realty
2. Gold Coast Greystone
This 7,600 square foot, five-story Greystone in Chicago’s Gold Coast features 5 bedrooms and 9 bathrooms on an oversized lot, and is listed at $5,495,000. Originally built in the early 20th century, the home has been meticulously restored to preserve historic elements like its architectural staircase and glass-on-onyx dome, while integrating modern conveniences including a Savant home system and snow melt walkways. Located near the Latin School and Lake Michigan, the property includes a two-car garage, multiple terraces, and a fully equipped lower level for guests or live-in arrangements.
Where is the Gold Coast Neighborhood?
The Gold Coast is a historic lakefront neighborhood just north of downtown Chicago. It features 19th-century mansions, luxury high-rises, and upscale shopping along Oak Street. The neighborhood includes access to Oak Street Beach and the Lakefront Trail. It’s known for quiet, tree-lined streets near the Magnificent Mile.
Living Room
Tall windows and neutral tones define the formal living room, which features a large area rug, low modern seating, and a circular mirror above a textured console. Along the far wall, three armchairs are arranged near the windows, bringing in views of fall foliage. To the left, an opening leads into a hallway with bold black-and-white tile flooring.
Kitchen
Surrounded by dark wood cabinetry, the kitchen is anchored by a marble island with seating for three. A large glass block window behind the stove and sink provides natural light while maintaining privacy. Counters and backsplash in black stone contrast with the warm wood floor and built-in appliances.
Dining Room
Centered by a round wooden table with eight velvet armchairs, the dining room is tucked into an alcove with a single large window framed by minimalist trim. Two abstract artworks hang on opposite walls, adding balance to the symmetrical layout. Inlaid wood flooring borders the space with a patterned edge.
Sunroom
Enclosed in glass walls and a sloped glass ceiling, the sunroom doubles as a sitting area with a small sofa, two armchairs, and a coffee table. One side opens to an outdoor brick patio with a spiral staircase and planter boxes. A sculpted wall panel and potted plants introduce texture against the otherwise sleek surfaces.
Bedroom
Double pocket doors connect the main bedroom to an adjoining lounge filled with natural light from full-height windows. Inside the bedroom, a king bed with layered pillows sits between two nightstands beneath a ceiling fan. Light wood flooring and a soft area rug finish the room’s clean layout.
Source: Brad Lippitz, Brittany Shapiro @ Compass via Coldwell Banker Realty
3. Private Compound in Historic Old Town
Set on nearly three lots in Chicago’s Old Town, this 7,528 square foot residence includes 4 bedrooms and 6 bathrooms, listed at $5,494,000. Originally anchored by a historic fire cottage, the property has been reimagined by Rugo Raff architects to blend architectural significance with advanced modern features, including heated walkways and a commercial-grade kitchen. The estate includes a main residence, separate coach house, private gardens, and an oversized 2.5-car garage, creating a discreet and expansive urban retreat.
Where is the Old Town Neighborhood?
Old Town is located just northwest of downtown Chicago and is known for its Victorian-era buildings and narrow streets. It’s home to the famed Second City comedy club and a mix of boutiques, bars, and restaurants. The neighborhood hosts the annual Old Town Art Fair. Wells Street serves as its main commercial corridor.
Foyer
Curved stairs wind upward from the entryway, where a sculptural console and artwork line the walls of this transitional space. On one side, a hallway leads into a wood-paneled room, while bold art and accent lighting add contrast. A dark floor and soft white walls keep the area visually grounded and open.
Living Room
Natural light fills the main living room, where floor-to-ceiling windows frame a view of the landscaped courtyard. A fireplace curves into one corner beside a symmetrical furniture layout with armchairs, a sofa, and a low table. Along one wall, a long wooden console supports framed artwork and accents.
Dining Room
Windows line the exterior curve of the dining room, wrapping a polished table surrounded by high-back chairs in dark upholstery. A fireplace is set into one wall, facing a console with art and minimal decor. Overhead, a circular light fixture mirrors the table shape while casting even illumination.
Bedroom
Tall glass doors open from the bedroom onto a balcony, drawing attention to an outdoor view surrounded by greenery. A curved ceiling detail mirrors the soft arch of the white fireplace inset with herringbone tile. The bed sits low with neutral bedding and a thick carpet spread across the dark floor.
Bathroom
Tile flooring and vertical surfaces define the bathroom, where an open walk-in shower features multiple wall-mounted fixtures. Natural light filters down from a high skylight above, casting light across the textured walls. Steps connect different sections of the room, which includes multiple entry points and wood-paneled doors.
Source: Jeffrey Lowe @ Compass via Coldwell Banker Realty
4. Modern Classic with Rooftop Deck
Located in Chicago’s Lincoln Park, this 4,000 square foot single-family home features 4 bedrooms and 4 bathrooms and is listed at $1,895,000. The property was expanded with a third and fourth story addition in 2012 and underwent a full renovation in 2021, including a kitchen upgrade and a dig-down for increased ceiling height. Highlights include a rooftop deck with a full outdoor kitchen and panoramic city views, along with modern amenities integrated into a historically charming layout.
Where is the Lincoln Park Neighborhood?
Lincoln Park stretches along the lakefront and includes the city’s largest park of the same name. It’s home to the Lincoln Park Zoo, DePaul University, and North Avenue Beach. The neighborhood mixes historic homes with shops, restaurants, and theaters. Armitage Avenue and Clark Street are key commercial areas.
Entrance
Brick walls and a green double door mark the entrance to a small patio area, furnished with a black-and-white striped seating set. Nestled between two buildings, the space includes a paver walkway and raised planting beds. Cushioned chairs and a metal table offer a compact outdoor lounging setup.
Living Room
Grouped armchairs surround a central glass table in the living room, placed on a rug in front of a traditional fireplace. Built-in window seating runs beneath a wide window, framed by wood trim and filled with potted plants. A set of French doors opens to a small outdoor area or balcony.
Kitchen
Open to a casual seating area, the kitchen features cream-colored cabinetry, a large island with marble counters, and a green range with brass hardware. Pendant lights hang above the island, which is lined with cane-back bar stools. In the background, a fireplace and windows connect the space visually to the adjoining room.
Bedroom
Wallpaper with a subtle repeating pattern wraps the bedroom, where a queen bed is flanked by blue nightstands and mounted reading lights. A double-door closet and small bench sit across from a wall-mounted television. French doors with dark trim lead to an exterior view or balcony.
Outdoor Kitchen and Lounge Area
Bar seating lines an outdoor kitchen and lounge area beneath a partially covered pergola roof. Stone walls and a built-in countertop frame the space, which includes multiple woven chairs and a row of barstools. Lounge chairs and small tables complete the layout, set against a backdrop of trees.
Source: Elizabeth Lothamer, Kiley Hackbarth @ Compass via Coldwell Banker Realty
5. Iconic Chicago Style
Blending architectural heritage with modern upgrades, this 4,492 square foot home in Lincoln Park offers 4 bedrooms and 4 bathrooms, listed at $2,700,000. Set on picturesque Seminary Street, the residence features a renovated chef’s kitchen, spa-inspired primary suite, and a finished lower level with radiant floors and a wet bar. Outdoor highlights include a brick patio and a newly built garage roof deck with a steel pergola, wet bar, and built-in seating, plus a heated 2.5-car garage.
Where is the Lincoln Park Neighborhood?
Where city streets meet green space, Lincoln Park blends urban life with nature. The neighborhood has a strong residential feel with many mid-rise buildings and brick row houses. It features a large farmers market at Green City Market in warmer months. Public transit access is strong with multiple ‘L’ train lines running through it.
Living Room With Dining Area
Tucked along one wall, the living and dining area shares an open layout with light wood floors, a modern fireplace, and minimal furnishings. A large sectional and two chairs center around a circular coffee table with a chess set, while a dining table extends toward the back. High ceilings and soft lighting emphasize the vertical space.
Kitchen
White cabinetry and pale stone countertops wrap around the galley kitchen, which features a cooktop with stainless steel hood and double ovens. Built-in shelving provides display space along the backsplash, and upper glass-front cabinets bring symmetry to the far wall. A deep sink and integrated refrigerator complete the layout.
Bedroom
Large windows with sheer curtains line the bedroom, where a king-size bed faces a fireplace topped with a mounted television. Integrated closets with brass hardware flank the fireplace wall, offering storage without crowding the space. Soft carpeting and armchairs near the window add warmth and seating.
Bathroom
Framed in glass, the bathroom features a deep soaking tub, walk-in shower, and long dual-sink vanity with dark stone countertop. Marble and white finishes dominate the room, balanced by frosted glass blocks along one side. A hexagonal tile floor and warm wood stool introduce subtle variation.
Rooftop Deck
Raised above the surrounding area, the rooftop deck is designed for entertaining with a dining table, built-in benches, and an outdoor kitchen setup. Slatted pergola structures and metal panels provide partial shade and privacy. Wood and brick surfaces form a mix of textures across the space.
Source: Deborah Ryder @ American International Realty via Coldwell Banker Realty
