Chicago Homes with Vintage Style

Chicago Homes with Vintage Style

Welcome to Chicago, the vibrant heart of Illinois and the third-largest city in the United States, nestled in the picturesque Cook County. Known for its stunning skyline, rich history, and diverse culture, Chicago offers a unique blend of urban sophistication and Midwestern charm. From the iconic architecture of the Willis Tower to the serene shores of Lake Michigan, this city is a haven for those who appreciate the finer things in life.

For homebuyers enchanted by the allure of vintage style, Chicago is a treasure trove of architectural gems. The city boasts a remarkable array of homes that reflect its storied past, featuring stunning details that transport you back in time. Imagine stepping into a beautifully restored Victorian with intricate woodwork, stained glass windows, and expansive porches that beckon you to relax and enjoy the neighborhood. Or perhaps a classic Chicago bungalow with its charming brick façade and cozy, inviting interiors is more your style.

These vintage homes are not just places to live; they are pieces of history, each telling a unique story of the families who have called them home. Many of these properties are located in historic neighborhoods, where tree-lined streets and community parks create a warm, welcoming atmosphere. Living in a vintage-style home in Chicago means embracing a lifestyle steeped in character and charm while being just a stone's throw away from world-class dining, shopping, and entertainment.

Explore the enchanting vintage homes of Chicago and discover a place where history, culture, and modern living beautifully intertwine. Your dream home awaits!

Newest Chicago Homes with Vintage Style

3017 E 78Th Street Unit #3A, Chicago
$75,000
1 Beds ⋅ 1 Baths ⋅ 12792870 MLS ⋅ NEW Status
Welcome home to this charming 1-bedroom, 1-bath co-op located in a classic building filled with timeless vintage character. This bright, inviting residence was tastefully updated in late 2020 and is offered fully furnished, including all appliances, making it truly move-in ready. Perfectly situated just steps from Rainbow Beach Park and the shores of Lake Michigan, you'll enjoy easy access to scenic walking and biking paths, tennis courts, and beautiful lakefront views. The co-op is conveniently located just one block east of South Shore Drive. Monthly assessments cover property taxes, heat, cooking gas, water, and building maintenance, providing exceptional value. Additional amenities include an on-site laundry facility, private storage, and permit parking. Board approval is required for the purchase. With ownership costs that are lower than many nearby rental options, this is an outstanding opportunity to own an affordable lakefront home.

3017 E 78Th Street Unit #3A, Chicago
810 W Lakeside Place Unit #107, Chicago
$299,900
2 Beds ⋅ 1 Baths ⋅ 12791314 MLS ⋅ NEW Status
Available for immediate occupancy! Welcome to this inviting two-bedroom, one-bath condo in a charming vintage courtyard building in Uptown. Beautiful wood floors and a cozy electric fireplace anchor the open living and dining area, creating a welcoming space to relax or entertain. The well-appointed kitchen features rich wood cabinetry, stainless steel appliances and convenient pantry storage. An updated bathroom, generous closets and rear outdoor deck space add comfort and everyday convenience. Enjoy a walkable neighborhood near Clarendon Park, the scenic lakefront and Montrose Beach, with cafes, restaurants and everyday shopping nearby along Wilson Ave and Broadway. Building amenities include common laundry, an exercise room and a separate storage locker. The monthly assessment includes heat and water. Pets and rentals are welcome. Nearby off-site parking is available for rent at Weiss Memorial Hospital.

810 W Lakeside Place Unit #107, Chicago
555 W Briar Place Unit #302, Chicago
$650,000
2 Beds ⋅ 3 Baths ⋅ 12792016 MLS ⋅ NEW Status
This impeccably maintained duplex offers an amazing floorplan with space to live, work, and entertain. Soaring high ceilings and hardwood floors throughout set the tone the moment you walk in. The main level features a large open-concept living and dining area flowing into a modern kitchen, perfect for everyday living and hosting alike. Two generously sized bedrooms include an en-suite primary, and not one but two private outdoor spaces extend your living area into the fresh air. Upstairs, a huge flex loft with its own full bath could easily serve as a third en-suite bedroom, home office, media room, or guest retreat. Bay windows and skylights flood the home with natural light throughout. Thoughtful extras include in-unit laundry and great additional storage. Set on a quiet, tree-lined street, the location is hard to beat, with so much to enjoy right outside your front door. Stroll to the shops, cafes, and restaurants along Broadway, head two blocks to the Lakefront Trail for runs, rides, and sunsets by the water, and commute with ease via the CTA and express buses. Space, light, flexibility, and an unbeatable East Lakeview address. This one is a must-see.

555 W Briar Place Unit #302, Chicago
3608 N Pine Grove Avenue Unit #B7, Chicago
$235,000
1 Beds ⋅ 1 Baths ⋅ 12792005 MLS ⋅ NEW Status
Welcome to this incredibly spacious and well-maintained 1-bedroom, 1-bath condominium in the heart of highly desirable Lakeview East! Offering approximately 900 square feet of comfortable living space, this charming English Garden end unit combines character, convenience, and an unbeatable location just moments from Chicago's lakefront. Step inside to discover an expansive floor plan featuring a decorative fireplace, generous living and dining areas, abundant natural light, and plenty of room to work, relax, and entertain. The beautifully landscaped courtyard creates a welcoming retreat right outside your door, while the common rooftop deck offers the perfect setting to enjoy grilling, entertaining, and breathtaking city and lake views. Additional conveniences include laundry facilities just steps from the unit, bike storage, and a large private storage space located directly across the hall. Monthly assessments provide exceptional value and include gas, water, garbage service, common insurance, landscaping, RCN cable, and internet.Perfectly positioned just one block from Chicago's iconic lakefront, Lake Shore Path, parks, and beaches, this home offers the ultimate walkable lifestyle. Enjoy easy access to Wrigley Field, neighborhood restaurants, cafes, shopping, grocery stores, public transportation, and the CTA Red Line for a quick commute downtown. This condo unit presents an outstanding opportunity for investors seeking immediate rental income or future homeowners looking to secure a home in one of Chicago's most sought-after neighborhoods. Pet-friendly building. Don't miss your chance to own an affordable piece of Lakeview living where city convenience, neighborhood charm, and lakefront recreation come together.

3608 N Pine Grove Avenue Unit #B7, Chicago
2100 N Lincoln Park W Unit #5EN, Chicago
$420,000
2 Beds ⋅ 2 Baths ⋅ 12790001 MLS ⋅ NEW Status
Welcome to 2100 N Lincoln Park West Unit 5EN, a 2-bedroom, 2-bath condo on the fifth floor of a classic 12-story brick doorman building at Dickens and Lincoln Park West, with windows overlooking the Lincoln Park Zoo directly across the street. The living room and both bedrooms have parquet floors and are finished with crown molding and built-in uplighting for full-room mood lighting. A dedicated dining nook sits between the living room and the separate tiled kitchen, which has wood cabinets, stainless steel appliances, and can lighting. Both bedrooms are on their own wing off a separate hallway, and the second bedroom also opens to the living room through a pair of double doors with full frosted glass panels. The primary has a long wall of closets and a tiled en-suite bath with a bathtub, and the tiled second full bath off the hall has a standing shower. The rooftop deck has a pool, lounge chairs, dining tables, and grills under a covered overhang, and residents also have door staff, an exercise room, an elevator, resident storage, and leased garage parking on site. The building has a coin laundry room, and owners are allowed to install a washer and dryer in the unit. South Pond, the Nature Boardwalk, the Lincoln Park Conservatory, the Peggy Notebaert Nature Museum, and the Lakefront Trail are all a short walk away, Clark Street restaurants and the #22 Clark bus are one block west, and Lake Shore Drive and the Red Line are both reachable at Fullerton.

2100 N Lincoln Park W Unit #5EN, Chicago
1200 N Lake Shore Drive Unit #405, Chicago
$475,000
1 Beds ⋅ 1 Baths ⋅ 12790531 MLS ⋅ NEW Status
A true Gold Coast jewel box, this Architectural Digest and MyDomaine-featured residence is the kind of home buyers search for but rarely find. Don't miss this beautifully restored designer home where timeless Chicago architecture meets modern luxury. Nestled within Benjamin Marshall's iconic 1912 boutique building at 1200 North Lake Shore Drive, Residence 405 captures everything buyers love about historic prewar homes: soaring 10.5-foot ceilings, exquisite original millwork, rich herringbone and chevron white oak floors, abundant natural light, and craftsmanship that simply cannot be recreated today. Thoughtfully renovated with a designer's eye, the nearly 19-foot kitchen is as beautiful as it is functional, featuring honed Italian marble countertops, floating Arabescato Gioia marble shelving, a Bertazzoni range, Fisher & Paykel refrigerator, Bosch dishwasher, and a custom built-in banquette that creates the perfect setting for morning coffee or intimate dinners. The spa-inspired marble bathroom rivals those found in homes at significantly higher price points, while the oversized 16' x 12' bedroom comfortably accommodates a king-size bed and offers a generous walk-in closet. A gracious foyer welcomes you home with a sense of arrival rarely found in a one-bedroom residence. Quiet western exposure fills the home with warm afternoon light and peaceful treetop views, creating a serene retreat in the heart of the city. Additional features include full-size Bosch in-unit laundry, Sonos sound system, smart thermostat, dedicated storage, and televisions that will remain with the home. Residents enjoy the intimacy of just 34 homes along with exceptional amenities including a spectacular vaulted marble lobby, 24-hour door staff, full-time engineer, fitness center, resident lounge, rooftop terrace overlooking Oak Street Beach and Lake Michigan, and recently completed lobby, elevator, and facade renovations. Perfectly positioned in Chicago's prestigious Gold Coast, just steps from Oak Street Beach, the Magnificent Mile, renowned restaurants, luxury boutiques, and the lakefront trail, this remarkable residence offers a rare opportunity to own a move-in-ready designer home in one of Chicago's most architecturally significant buildings. Some homes impress. This one leaves a lasting impression.

1200 N Lake Shore Drive Unit #405, Chicago
1522 E 59Th Street Unit #3E, Chicago
$117,900
1 Beds ⋅ 1 Baths ⋅ 12790484 MLS ⋅ NEW Status ⋅ Midway View BLDG.
This top floor junior one bedroom in a courtyard building facing the Midway Plaisance packs a punch. Flanked by the University of Chicago campus and the newly opened Obama Center, the location is getting a lot of buzz. It's also super convenient, with immediate access to transportation. The Metra Electric station is within two minutes' walking distance, just beyond the Divvy bike station, while the #6, #10 and #28 bus stop is one block east. A short stroll/5 minute bike ride takes one to historic Jackson Park and the lakefront bike trail. There is ample street parking, and a garage space may be available for rent in a nearby garage. The building, designed by Paul F. Olsen and built by Albert W. Swayne in a quirky "Mediterranean-Gothic" style, has all the hallmarks of '20s charm and efficiency. The compact interior features hardwood floors, picture frame molding, 9' ceilings, an eat-in kitchen, a workspace niche, built-in cedar wardrobe and storage, and a vintage bathroom with penny floor tile, subway wall tiles and a deep soaking bathtub. The unbeatable low assessment of $364 covers heat, cooking gas, property taxes, water, common insurance and exterior maintenance. For location, convenience and economy, it's a standout. Sorry, no investors. Sold as-is.

1522 E 59Th Street Unit #3E, Chicago
7635.5 N Greenview Avenue Unit #3S, Chicago
$219,900
2 Beds ⋅ 2 Baths ⋅ 12788917 MLS ⋅ NEW Status

7635.5 N Greenview Avenue Unit #3S, Chicago
5555 N Sheridan Road Unit #1508, Chicago
$385,000
2 Beds ⋅ 1 Baths ⋅ 12788966 MLS ⋅ ACTIVE Status ⋅ Edgewater Beach Apts BLDG.
This elegant 2-bedroom | 1-bathroom apartment at the EBA has been beautifully restored and features unique and thoughtful touches not found in other apartments. Discerning buyers will appreciate everything from the custom updated kitchen and the all-marble bathroom to the added millwork and ambient lighting. The gracious living room has room enough to host large gatherings, while the bay window invites in natural light and frames beautiful sunsets. There is a partial wall between the living room and dining to create some separation while still having a sense of openness. The galley kitchen was joined with the adjacent storage area creating space for additional cabinets and a small cafe table or desk. The kitchen has custom cabinets, Blue Pearl countertops and SS appliances. The primary bedroom has two large closets, space for a king bed and beautiful, sunny views. The second bedroom features custom bookcases and is currently used as an office. The all-marble bathroom has a barrier-free shower and custom vanity. You will find hardwood floors throughout, plaster walls and updated wiring. Enjoy a beautiful apartment in aMonthly assessments include property taxes, heat, cable, Internet, cooking gas, water, use of all amenities and a contribution to the reserve fund. The EBA is a co-op building that requires a minimum of 10% down. Leased parking is available for $120/month. Sorry, dogs are not allowed. 115 shares. Enjoy the lakefront bike path and beaches, Bryn Mawr Historic District, Andersonville & easy public transportation.

5555 N Sheridan Road Unit #1508, Chicago
5300 S Shore Drive Unit #111, Chicago
$200,000
4 Beds ⋅ 3 Baths ⋅ 12788214 MLS ⋅ ACTIVE Status ⋅ Hampton House BLDG.
Welcome home to gorgeous views from this spacious 11th floor Hyde Park condo. Enter from 53rd street, go through the elegant, doorstaffed lobby, and up the elevator to the 11th floor. This is a NE corner unit with views of the Lake and downtown. On a clear day, you can see Indiana across the Lake. Walk all the way down the hall and enter on your left. Step inside, leave your coats and shoes in the hall closet and turn right into the primary bedroom. This extra large bedroom has an East facing view offering an unobstructed view of the Lake. There is a walk-in closet with professional organization and a primary bath with a stand alone shower. Keep going back to enter the central hub of the unit. On the right is the living room with a full wall of built-in bookcases and the same beautiful view as the primary bedroom in addition to a Northern facing window. There are 3 additional bedrooms, 2 with a full attached bathroom. The galley kitchen is off the central hub and has a separate access door to the hallway. This unit is LARGE and has over 2300 square feet. There is Central Air in this unit, coin laundry in the building. With huge potential for updates, beautiful views, public parks, restaurants, shopping, grocery stores, blocks from the MSI, and access to public transportation, this is a unique opportunity to own a real Hyde Park gem. HOA FEE include- AND EVERYTHING ELSE BESIDES WIFI, AND cOMED

5300 S Shore Drive Unit #111, Chicago
5616 S Kimbark Avenue Unit #3, Chicago
$385,000
3 Beds ⋅ 2 Baths ⋅ 12786659 MLS ⋅ ACTIVE Status
Sitting across the street from the playground of the famed Ray School and in the midst of the University of Chicago campus, this perfectly situated condominium building has its own fenced private garden and garages in the rear. Stunning leaded glass windows and doors, beamed ceilings, beautifully finished original woodwork and built-ins, gleaming hardwood floors and a gracious woodburning fireplace are just the beginning of this home's attractions. The kitchen was reconfigured and opened to the original dining room to create an expansive open living area with great light and space. The sunroom in the rear is filled with afternoon sun and is a lovely dining room. The original living room up front has been reimagined into a spacious primary bedroom with a Prairie Style fireplace flanked by built-in bookshelves and 4 leaded glass windows overlooking the tree lined street. In fact, all of the windows look out to expansive views. Two additional bedrooms make this a home large enough for a good sized household. The kitchen has white shaker wood cabinets, some with glass fronts. The farmers sink, open shelving, quartz counters and beadboard backsplash are evidence of a creatively designed space. Stainless steel appliances, of course. There is a newer half bath off the kitchen. The full bath has a footed tub outfitted with a shower head and hand shower, a vintage pedestal sink and a tall charming vintage built-in cabinet for storage. Next to the back door leading down to the communal yard and garages is the laundry and pantry. There is a separate room in the garage for grills and another for bicycles. There are 4 individual garages for the six units. Each unit has the opportunity to rent a garage for 4 years and then will spend 2 years without a garage. The current owners have never rented any of the garages in the years they have lived there. They say it's never been a problem parking on the street. The garage rental is $100/mo. In the basement are laundry machines for the use of all the owners, but you might have scant use for them since there are machines in the unit. A brand new boiler is has just been installed and is ready for the heating season. The sellers have use of 5 private storage rooms in the basement! This is a terrific condominium home in a simply terrific location. If you want to get anywhere on campus or to the Lab Schools, the walk or roll are easy and lovely. Restaurants and bookstores line 57th St. The Metra and express buses are just a few blocks to the east. The Museum of Science and Industry and the Obama Center are just beyond those. The lakefront and its great path and beaches are on the other side of DuSable Lake Shore Drive accessible via the 57th St underpass or the underpass to Promontory Point. It's easy to get to the Trader Joe's and Walgreens and the other shops and restaurants in the Hyde Park Shopping Center. Just north are the shops and foodie restaurants of 53rd St. Whole Foods is just beyond. On 55th St to the west are restaurants, a bowling alley, the Court Theater and the Smart Museum. Lots of culture and lots of fun all around you.

5616 S Kimbark Avenue Unit #3, Chicago
1120 N Lake Shore Drive Unit #15A, Chicago
$750,000
3 Beds ⋅ 2 Baths ⋅ 12784560 MLS ⋅ ACTIVE Status
**Iconic Lake Shore Drive Living in the Heart of the Gold Coast** Set within an architecturally significant building in one of Chicago's most prestigious neighborhoods, this approximately 1,800-square-foot co-op residence offers timeless elegance, generous living spaces, and breathtaking, unobstructed views of Lake Michigan, Oak Street Beach, and the iconic curve of Lake Shore Drive. The gracious living and dining rooms feature hardwood floors, classic crown moldings, and a fireplace, creating an inviting setting for both everyday living and entertaining. An updated kitchen blends modern convenience with the home's enduring character. Two en-suite bedrooms provide comfort and privacy, while the third bedroom/den - currently configured as a home office - features custom desk space and built-in cabinetry. Perfectly positioned on the 15th floor, the residence offers an ideal vantage point-not too high and not too low-to appreciate the beauty of Chicago's lakefront and surrounding skyline. With its classic proportions, remarkable views, and exceptional location, this is a rare opportunity to make a distinguished Lake Shore Drive address your own.Enjoy the best of the Gold Coast just outside your door, with acclaimed restaurants, premier shopping, the lakefront, and Lincoln Park all within easy reach. Building amenities include a renovated fitness room and an outdoor courtyard and patio. The monthly assessment includes property taxes, offering the convenience of a simplified ownership structure. A classic Chicago residence with iconic views, enduring architectural character, and a front-row seat to the best of city living.

1120 N Lake Shore Drive Unit #15A, Chicago
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