Chicago Homes with Vintage Style

Chicago, located in the state of Illinois and Cook County, is a vibrant city known for its rich history, stunning architecture, and diverse neighborhoods. It offers a unique blend of urban living and cultural experiences, making it an attractive destination for both residents and tourists alike.

One of the charming aspects of Chicago is its abundance of homes with vintage style. True to its nickname, the "Windy City," Chicago boasts a wide range of architectural styles, including Victorian, Queen Anne, Tudor, and Craftsman, among others. These homes exude character and charm, with intricate details, ornate woodwork, and unique features that reflect the city's history.

Living in a vintage-style home in Chicago allows residents to immerse themselves in the city's past while enjoying modern amenities. Many of these homes have been lovingly restored and updated to meet the needs of today's homeowners while preserving their original charm. From cozy bungalows to grand mansions, there is a vintage-style home in Chicago to suit every taste and budget.

In addition to their architectural appeal, vintage homes in Chicago are often located in well-established neighborhoods with tree-lined streets and a strong sense of community. Residents can enjoy a slower pace of life while still being close to the city's vibrant downtown area, world-class dining, shopping, and cultural attractions.

Whether you're a history enthusiast, an architecture lover, or simply appreciate the timeless beauty of vintage homes, Chicago offers a plethora of options to explore and call home.

Newest Chicago Homes with Vintage Style

$89,000

1 Beds ⋅ 1 Baths ⋅ 12757185 MLS ⋅ NEW Status

Coveted Cylinder Unit with lovely kitchen and dining room lake views in the historic Park Shore. Enjoy stunning views of the garden, lake, and museum from this beautiful space. Features include elegant hardwood floors and a charming decorative fireplace. Residents have access to a party room, gym, and guest room for visitors. Conveniently walk to the beach, Promontory Point, the University of Chicago, a variety of restaurants, Trader Joe's, shopping, and more. Public transportation is easily accessible with nearby bus and train lines. Please note that taxes and utilities are included in the assessment fees of this Building.

1755 E 55Th Street Unit #605, Chicago

$399,000

1 Beds ⋅ 2 Baths ⋅ 12755947 MLS ⋅ NEW Status ⋅ Franklin Lofts BLDG.

Lovingly designed loft space in the heart of Printer's Row in the historic Franklin Building. 9 tall windows (3 of them in the bedroom) flood the place with afternoon sunshine. Wide open traditional loft space with high ceilings, exposed brick, concrete pillars and beams and genuine oak floors dating from the condo conversion in 1989. Because the building was created for printing presses, the subfloors are thick concrete so you will never hear anyone from above or below. The loft has been fitted out with an amazing amount of storage. Massive built-in open shelved bookcases extend from floor to ceiling on the entire south wall of the living room. There is another floor to ceiling bookcase on the east wall as well as two floor to ceiling storage closets. Along the north wall are closets for coats and shelving. A wonderful banquette with room for baskets beneath is tucked into the window wall on the northwest corner of the room creating a cozy spot for eating or curling up in the afternoon sunshine with a book. Remote controlled shades and lighting installed in 2023. The contemporary open kitchen has wood cabinets, granite countertops, distinctive backsplash tiles and SS appliances including a new (2025) range and dishwasher. Both the half bath and the full bath have been updated. The full bath has a glass enclosed shower with a pebble stone wall and a double vanity with 2 Mexican handcrafted sinks. The toilet is in a separate compartment which also includes the front loading laundry machines. The fully private bedroom has 3 large windows, floor to ceiling closets and more bookshelves. The powder room has a full wall and backsplash of hand crafted Mexican tiles and a Mexican sink set in a unique wood slab counter. Possibilities are endless in this airy condominium. Because there are so many windows with frontage on the street, more rooms could be created or reconfigured. There are no structural walls because of the concrete pillars and beams. For those who live on this special block of the city, there is nowhere else they'd rather be. It is in the center of the transportation hub of the metropolis. All of the CTA train lines have stops within 2 blocks of the building. There is a Red Line stop right outside on Polk. It's easy access to all of the highways from Ida B Wells Drive just 2 blocks north including easy access to DuSable Lake Shore Dr. Buses stop across the street. The neighborhood is brimming with restaurants, bars & shops. It's an easy walk or roll to Grant Park, Buckingham Fountain, Millennium Park, the museums, theaters, universities, and all of the shopping and eating in the Loop. You can head south and be at the University of Chicago and its hospitals in minutes or head west and be at the UIC campus and its nearby hospitals even sooner. Walk Score says it's a walker's and public transportation rider's paradise. The vaunted 2-way protected bike path that runs all the way through the Loop and over the river begins outside the front door. Parking garages and a parking lot surround this building. The parking offered would be offsite and leased separately, but you'll rarely have to use a car. There is a bike room in the basement next to the coin laundry which is available to use if you have bulky items. The building engineer is competent and friendly, and the management company is miraculously accessible. There is a large service elevator that opens to the street for easy move-in and out that recalls its days of hauling heavy loads of paper. This building is carefully run by an attentive board and management. The reserve is at $1,100,000 and there hasn't been a special assessment in over 25 years. EVERYTHING is included in the assessment except electric. That includes high speed internet and basic cable from Astound. The building is about to embark on a renovation of the hallways and foyer to address its modern needs (larger package room for post-pandemic deliveries) while enhancing its very special vintage character

720 S Dearborn Street Unit #504, Chicago

$475,000

2 Beds ⋅ 2 Baths ⋅ 12753357 MLS ⋅ NEW Status

Chicago

$425,000

2 Beds ⋅ 3 Baths ⋅ 12756053 MLS ⋅ NEW Status ⋅ Edgewater Beach Apts BLDG.

This 2-bedroom | 3-bathroom apartment feature a classic 6-room corner floor plan. Positioned on the northeast corner of the building, it offers pretty exposures of the park and lake and lots of natural light. The gracious floor plan flows seamlessly from the foyer into the large living room and dining room. The maid's room is used as a guest room, but it could also make a great office. The wall between the maid's room and galley kitchen could be removed to create a larger kitchen. The updated kitchen features original maple floors, a pantry, newer cabinets, appliances and counters. There are two generous bedrooms both with en-suite bathrooms. In-unit laundry is permitted in the bathroom next to the kitchen. Enjoy resort like living at the Benjamin Marshall designed Edgewater Beach Apartments. Amenities include an indoor swimming pool, 2-acres of green space, a library, a nicely equipped exercise room, 24-hour door staff, on-site management and unparalleled access to the lakefront. Monthly assessments include property taxes, heat, basic cable, Internet, cooking gas, water, use of amenities and more. The building requires a min. down payment of 10%. Leased garage parking is available for $115/month. Sorry, dogs and rentals are not allowed. Enjoy the lakefront, Bryn Mawr Historic district, Andersonville and easy public transportation.

5555 N Sheridan Road Unit #515, Chicago

$625,000

1 Beds ⋅ 1 Baths ⋅ 12754504 MLS ⋅ NEW Status

This classic Gold Coast one-bedroom, one-bath residence on coveted State Parkway offers an exceptional opportunity to experience quintessential Chicago living. Whether envisioned as an elegant pied-a-terre or a full-time city residence, this home combines timeless architectural character with an enviable location. Nestled among some of Chicago's most iconic historic landmarks, the residence sits next to the original Playboy Building and just around the corner from the legendary Three Arts Club. Originally owned by renowned interior designer, Michael O'Malley, the home retains many of its original architectural elements, thoughtfully preserved to honor its history. The original fireplace, a true focal point of the living space, has been lovingly restored by the current owner. Unusually generous proportions distinguish the residence, with an expansive living room, oversized bedroom, abundant closet and storage space, and nearly 10-foot ceilings creating a sense of scale rarely found in a one-bedroom home. Gorgeous crown molding and dramatic dark-stained parquet floors create an unmistakably elegant Chicago aesthetic. The living room overlooks State Parkway from a particularly picturesque stretch where street parking is not permitted, allowing the idyllic view to remain beautifully unobstructed. The galley kitchen preserves valuable square footage for the residence's unusually generous living and bedroom spaces. The sizable primary suite provides an inviting retreat and connects to a generously proportioned bath which offers exceptional space and flexibility for future personalization. Additional amenities include an extra-large private storage unit and free laundry conveniently located just steps from the residence. The beautifully maintained building also features a wraparound brick-paver patio surrounded by lush landscaping, an inviting and sophisticated setting to relax and unwind. And then there is the location. From this exceptional Gold Coast address, the lakefront, Magnificent Mile, world-class shopping and some of the city's finest dining are all just moments away. This is a rare opportunity to own a piece of historic Chicago architecture in one of the city's most coveted neighborhoods.

1350 N State Parkway Unit #GN, Chicago

$1,400,000

3 Beds ⋅ 5 Baths ⋅ 12670499 MLS ⋅ NEW Status ⋅ Powhatan BLDG.

Perched on the 11th floor of the iconic 1929 Art Deco Powhatan, this exceptional residence offers a rare combination of luxury, elegance, and comfort. Widely regarded as one of the building's finest apartments, this expansive single-level home is larger than many houses and showcases breathtaking lake and park views, among the best in the city. Meticulously renovated and presented in move-in condition, the residence is flooded with natural light and thoughtfully designed for both grand-scale entertaining and everyday living. Highlights include a stunning chef's kitchen with top-of-the-line appliances, an estate-sized butler's pantry, a formal dining room, soaring ceilings, hardwood floors, a beautiful fireplace with a hand-carved mantel, two-zone central air conditioning, and a spacious in-unit laundry room. The private living quarters feature three generously sized bedrooms, abundant closet space, and beautifully re-imagined en-suite baths, including dual primary baths. The Powhatan is renowned for its striking Art Deco architecture and distinguished amenities, including a restored lobby, indoor swimming pool, fitness center, and a spectacular rooftop ballroom with expansive terraces for outdoor dining and entertaining. This full-service co-op offers 24-hour door staff, valet parking, elevator attendants, on-site maintenance personnel, and private storage. Monthly assessments include parking, real estate taxes, and an unparalleled level of service. Significant capital improvements completed over the past decade have further enhanced the building's infrastructure and long-term value. A truly one-of-a-kind residence in one of Chicago's most celebrated landmark buildings.

4950 S Chicago Beach Drive Unit #11A, Chicago

$419,500

3 Beds ⋅ 2 Baths ⋅ 12755319 MLS ⋅ NEW Status

Character, charm, and comfort in the heart of Hyde Park. Flooded with abundant natural light and exceptionally quiet, this top-floor condo is a peaceful urban retreat. The home opens with a welcoming foyer featuring ornamental millwork framing the entrance to the living room. Three bedrooms and two updated baths provide comfortable, flexible living. The expansive living room centers on a classic fireplace with a gas-starter, bounded by built-in bookcases. An enclosed front sunroom, featuring new terra cotta floors and newer windows, offers treetop views - a small park sits directly across the street - and a serene space for morning coffee or an afternoon read. You'll appreciate the incredible sunlight that bathes this room and carries throughout the entire home. A formal dining room with original built-in cabinetry flows seamlessly into the updated kitchen, complete with maple cabinetry, Corian counters, stainless appliances, and a butcher block prep space set over an in unit washer and dryer. The kitchen also features a separate pantry with new shelving and a chest freezer. Hardwood floors run throughout, including newer flooring in the kitchen. Updated electrical and plumbing further set this unit apart from others in the building. A rear deck overlooks a shared yard, recently landscaped to include a terrace, individual garden plots, and a parking space. Pets welcome. Assessments include the cost of heating and the building is professionally managed by Marian Realty. The front facade of the building was tuckpointed and painted in 2023. Large storage space in basement. Steps from Trader Joe's, Whole Foods, the University of Chicago, and the shops and restaurants of 53rd Street, with effortless access to the Metra and CTA.

5321 S Woodlawn Avenue Unit #3S, Chicago

$183,000

1 Beds ⋅ 1 Baths ⋅ 12750027 MLS ⋅ NEW Status

Prepare to fall in love with this spacious 1 bedroom condo in idyllic Edgewater! This unit features an updated kitchen with granite counters, maple cabinets and the separate dining room affords you extra space rarely seen in a condo at this price point. You will love the vintage features like hardwood floors and built in closets. Your houseplants will love the sunny western exposure from the 2nd floor windows! Well run, professionally managed building with great curb appeal. Heat included in the assessments! Amenities include coin-op laundry, private storage and a separate bike storage room. Situated on the west side of Edgewater proper, this quiet, tree-lined street is nonetheless conveniently located close to Andersonville's amazing restaurants & nightlife and the Metra. And all within just a short walk or bike ride to the Red line and lakefront.

1750 W Granville Avenue Unit #2A, Chicago

$1,560,000

3 Beds ⋅ 3 Baths ⋅ 12707624 MLS ⋅ NEW Status

Experience refined Gold Coast living in this architecturally-distinguished full-floor residence, occupying an entire level of an exclusive boutique 3-story elevator building. Offering exceptional privacy and timeless elegance, this meticulously-maintained home showcases sophisticated design, premium finishes, and modern updates throughout. The expansive living and dining spaces are flooded with natural light through 4 oversized windows overlooking picturesque Scott St, creating the perfect setting for both everyday living and elegant entertaining. Rich architectural details include soaring 9-ft ceilings, intricate dentil moldings, a wood-burning fireplace with gas starter, and custom bead-and-rail millwork accented by stately columns. The chef's kitchen is a true showpiece, featuring renowned Bulthaup cabinetry, Gaggenau appliances, a Sub-Zero refrigerator with additional freezer drawers, built-in steamer, Franke sinks, and striking Blue King granite countertops - designed to satisfy the most discerning culinary enthusiast. The luxurious primary suite offers a serene retreat with a stunning onyx spa bath, an expansive walk-in closet, and an adjoining den that can easily serve as a 4th bedroom, private office, or sitting room. 2 additional generously-sized bedrooms and beautifully-appointed bathrooms complete the home's thoughtful layout. Smart home technology includes Lutron lighting and a Crestron automation system controlling audio/visual, security, and climate. Recent mechanical updates provide added peace of mind, including a new air conditioning system installed in September 2025, a washing machine replaced in 2019, a dryer replaced in 2022, and professionally painted throughout recently. Perfectly positioned in 1 of Chicago's most coveted neighborhoods, you will enjoy being just a 5-minute walk to Oak St Beach and Lake Michigan, along with world-class shopping, fine dining, and many of Chicago's premier restaurants. A deeded garage parking space completes this exceptional offering.

24 E Scott Street Unit #2, Chicago

$650,000

2 Beds ⋅ 2 Baths ⋅ 12753112 MLS ⋅ NEW Status

Welcome to this beautifully rehabbed 2-bedroom, 2-bath condo in a charming vintage brick building in the heart of Lakeview! The home seamlessly blends classic Chicago character with modern luxury. The spacious open-concept living area is filled with natural light and architectural charm. Special details include a coffered ceiling, a bay window overlooking the tree-lined street, gas fireplace, and hardwood floors throughout. The gourmet kitchen features newer SS appliances, tumbled marble backsplash, copper hood, and granite counters w/ a breakfast counter w/ room for stools. The generously sized primary suite (currently used as a nursery) offers a luxurious en-suite bath featuring walk-in shower & separate jetted tub. The spacious second bedroom provides direct access to the home's exceptional year-round screened-in porch, which can also be accessed from the hallway. The second full bathroom is equally impressive, featuring beautiful stone finishes and a walk-in glass shower. One exterior parking spot and storage are included. Enjoy the best of Lakeview - walk to the Lake, Southport Avenue, Fresh Market, the new Whole Foods at Clark and Belmont, & the Wellington Brown Line "L"!

839 W Wellington Avenue Unit #2, Chicago

$899,999

4 Beds ⋅ 4 Baths ⋅ 12754732 MLS ⋅ NEW Status

Welcome to Residence 3E at 232 E. Walton Place, an extraordinary 3,800-square-foot home nestled within one of Chicago's most distinguished prewar co-op buildings, just moments from Lake Michigan and the Magnificent Mile. Designed by renowned architect John Fugard, this impeccably maintained residence seamlessly blends historic grandeur with modern livability, offering the scale and comfort of single-family living within an intimate 20-unit, elevator building with only two homes per floor. A gracious gallery foyer introduces the home's preserved architectural details, including exquisite moldings, rich hardwood floors, soaring ceilings, and oversized windows framing picturesque treetop views. Each room featuring its own distinct hand-painted design, further define every space and celebrate the craftsmanship rarely found in today's homes. Thoughtfully curated for both grand entertaining and comfortable everyday living, the floor plan offers exceptional separation between formal and informal spaces. The elegant living room is anchored by a stately gas fireplace, bathed in southern light and bordered by original picture frame moldings. While the formal dining room overlooks the beautifully landscaped courtyard, creating an inviting setting for intimate dinners and large-scale entertaining. Adjacent to the living room, a sophisticated library or home office with an ensuite bath offers exceptional flexibility and can easily be converted back into a fourth bedroom. At the heart of the home, the kitchen balances timeless character with everyday functionality. The original butler's pantry cabinetry has been thoughtfully preserved and enhanced with modern pull-out storage and glass display cabinets for fine China. A rare five-foot nickel farm sink and the home's iconic Magic Chef range, complete with eight burners, double ovens, broilers, and a warming drawer, create a true culinary experience. Beyond the kitchen sits a family room providing the perfect lounge space, while an oversized laundry room, walk-in storage room, and additional powder room enhance the home's functionality. Privately tucked away, the bedroom wing is centered around a secondary gallery foyer. The serene primary suite offers generous proportions, south-facing windows overlooking the treetops along East Walton Place, two walk-in closets, and a well-appointed ensuite bath featuring dual vanities, a soaking tub with shower, and a separate walk-in shower. Two additional oversized bedrooms overlook the manicured courtyard while offering abundant closet space and a Jack-and-Jill bathroom. Residents enjoy 24-hour door staff, professional on-site maintenance, and a private brick paver courtyard featuring beautifully landscaped gardens, outdoor dining areas, grilling stations, lounge seating, a children's play area, and a dedicated dog run. Ideally located on picturesque East Walton Place, just moments from Oak Street Beach, Lake Shore Drive, world-class shopping and dining along Michigan Avenue, Lake Shore Park, renowned museums, and Chicago's lakefront trail. Residence 3E presents a rare opportunity to own a pristine, architecturally significant home in one of Chicago's most historic co-op buildings, where timeless grandeur has been beautifully preserved for modern living.

232 E Walton Place Unit #3E, Chicago

$299,900

2 Beds ⋅ 1 Baths ⋅ 12753511 MLS ⋅ NEW Status

This beautiful courtyard building featuring a two bed, one bath condo is just steps from the lakefront and Montrose harbor. With an open floor plan, hardwood floors throughout and an outdoor deck space, this home is not to be missed. Each room provides ample closet space, the bathroom is updated and the living room features an electric fireplace. The building includes: two laundry rooms, a community exercise room, storage locker (#24) and nearby parking garages. In unit laundry cannot be added. Rentals and pets ARE welcome! (Unit is currently rented through April 30, 2027. Current rent is $2,100. Good tenants, great investment opportunity.)

810 W Lakeside Place Unit #107, Chicago

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