Chicago Homes with Vintage Style

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Newest Chicago Homes with Vintage Style

$160,000

1 Beds ⋅ 1 Baths ⋅ 12771801 MLS

Stop Making Your Landlord Rich. Start Investing in Yourself. In the heart of Woodlawn, this beautifully updated co-op offers approximately 800 square feet of flexible living space and an opportunity to move from renting into ownership. Unlike a condominium, a co-op purchaser generally acquires shares in the corporation that owns the building along with the right to occupy the residence. Here, the monthly assessment includes water, heat and real estate taxes. This oversized one-bedroom offers the potential for a second bedroom, home office, study or guest space, subject to applicable co-op approvals. Recent improvements include updated kitchen cabinetry, stainless-steel appliances, a neutral bathroom, refinished hardwood floors, new windows and refurbished radiators with new valves. Laundry and additional storage are located in the basement. The location is equally compelling-near the University of Chicago and its medical campus, with convenient access to Woodlawn, Hyde Park and the Obama Presidential Center area. For buyers who value space, flexibility and location, this residence offers a practical path to ownership in one of Chicago's most recognizable South Side communities. Rent provides a place to live. Ownership gives you the opportunity to build something for yourself.

6102 S Kimbark Avenue Unit #2W, Chicago

1425 W Summerdale Avenue Unit #3A, Chicago

$425,000

2 Beds ⋅ 1 Baths ⋅ 12775941 MLS ⋅ Andersonville BLDG.

Spectacular Penthouse views from this classic courtyard building in the heart of Andersonville. Open concept 2BR condo with abundant light. Original hardwood flooring and natural light streaming in through the bay window area. The living room features a wood burning fireplace and leads to a seating area with bay window--perfect for a reading nook or gazing out beautiful Andersonville from above the tree tops. The dining area is large enough to accommodate an 8-top table. The kitchen is well-equipped with new KitchenAid stainless appliances (2019/2020), ample cabinet storage and a unique mosaic countertop. The kitchen leads to a small balcony that only this unit has access to , and is large enough for a small love seat. Both bedrooms are typical vintage bedroom sizes and have great closet space. The primary bedroom looks out into the treetops, while the second bedroom has a murphy bed--perfect for a work from home space. Bathroom was a total gut in the last 2 years, all marble, Kohler air bath tub and Kohler fixtures. 2 new smart LG A/C units. Walking distance to everything Andersonville has to offer, just one block away. The best restaurants, nightlife, grocery stores, coffee shops, summer festivals (like Midsommar Fest!) and public transit are all at the end of the street. Rental parking options in the area.

1425 W Summerdale Avenue Unit #3A, Chicago

$1,600,000

3 Beds ⋅ 4 Baths ⋅ 12772455 MLS

A rare offering in one of Chicago's most distinguished residential buildings, this expansive Gold Coast residence pairs the grandeur of 1920s architecture with the ease of modern living. Set within the intimate Beaux-Arts elegance of 1325 N. Astor-a 1928 building designed by renowned Chicago architect Andrew Rebori of Rebori, Dewey & Wentworth-this 3 bed/4 bath home spans approximately 4,300 square feet, with serene treetop views and an exceptional collection of original details. Private elevator access opens directly into a gracious foyer, setting the tone for rooms defined by beautifully preserved hardwood floors, intricate millwork, solid wood pocket doors and era-appropriate light fixtures, including several antique pieces. The formal living room centers on a wood-burning fireplace with an exquisite hand-carved original surround and mantel, while the dining room offers an elegant setting for entertaining. The thoughtfully updated kitchen brings a contemporary sensibility to the classic architecture, with custom Shaker cabinetry, natural stone countertops, a generous island and professional-grade stainless-steel appliances, complemented by a breakfast nook, wine refrigerator and wood-clad butler's pantry with wet bar. A spacious family room features handsome built-ins, exceptional millwork and a second fireplace with marble surround, while a custom office and dedicated laundry room add convenience. The private quarters include a serene primary suite overlooking Astor Street, with treetop views and a beautifully appointed bath featuring a dual vanity, soaking tub and glass-enclosed shower. Two additional bedrooms each have their own full bath, including one with a clawfoot tub. The boutique, full-service building offers 24-hour door staff, attached heated garage parking, personal storage, a bike room and garden-level workout room. (ONE garage space is included.) Moments from Lake Michigan, Oak Street Beach, the Lakefront Trail and the Gold Coast's celebrated shopping and dining, this is Chicago apartment living at its most timeless.

1325 N Astor Street Unit #2, Chicago

5555 N Sheridan Road Unit #1612, Chicago

$179,900

2 Beds ⋅ 1 Baths ⋅ 12775331 MLS ⋅ Edgewater Beach Apts BLDG.

Welcome to the iconic Edgewater Beach Apartments, one of Chicago's most recognizable and beloved architectural landmarks, nestled in the heart of the historic Bryn Mawr District. Currently undergoing its first exterior repaint in more than 25 years, this nearly century-old building is being thoughtfully restored to its original "Sunset Pink" color, further elevating the beauty and prestige of this celebrated lakefront address. Offered for the first time in over 25 years, this exceptional residence reflects decades of pride in ownership. Meticulously maintained and lovingly cared for by the same owner, the home offers a rare opportunity to own a piece of Chicago history while preserving the timeless charm, warmth, and character that make residences in Edgewater Beach Apartments so special. This rarely available 16th-floor, east-facing residence offers something few units in the building can claim: unobstructed, panoramic views of Lake Michigan from nearly every room. Wake up each morning to breathtaking sunrises over the water and enjoy the ever-changing scenery that makes this one of the most desirable exposures in the entire building. Spanning approximately 1,200 square feet, the home features two generously sized bedrooms, a spacious kitchen with an oversized walk-in pantry, a large formal dining room perfect for entertaining, and wonderfully proportioned living spaces that showcase the craftsmanship and thoughtful design of a bygone era. Hardwood floors, abundant closet space, natural light, and classic architectural details create a home that feels both elegant and inviting. While exceptionally maintained throughout, the residence also presents an exciting opportunity for the next owner to personalize the space over time while enjoying its remarkable condition from day one. Edgewater Beach Apartments is renowned for offering one of the most comprehensive amenity packages on Chicago's lakefront, including 24-hour door staff, an indoor swimming pool, fitness center, library, arcade, ping-pong room, on-site dry cleaner, restaurant, and a beautifully landscaped private two-acre park and garden exclusively for residents. Garage parking is available for just $115 per month. Beyond the building, enjoy one of Chicago's most vibrant and walkable lakefront neighborhoods. Step outside your door and stroll to Foster Beach, Kathy Osterman Beach, Berger Park, the Lakefront Trail, and miles of shoreline along Lake Michigan. Grab your morning coffee at The Coffee Studio, Metropolis Coffee Company, or Heritage Outpost, meet friends for dinner at neighborhood favorites including Little Bad Wolf, Beard & Belly, Hopleaf, Moody's Pub, Francesca's Bryn Mawr, and Indie Cafe, or enjoy convenient shopping at Whole Foods, Mariano's, Jewel-Osco, and Edgewater Produce. Commuting is effortless with the CTA Red Line stations at Bryn Mawr, Berwyn, and Thorndale just blocks away, express bus service along Sheridan Road, and convenient access to Lake Shore Drive via Foster Avenue. This exceptionally well-managed co-op offers tremendous value with assessments that include property taxes, 24-hour door staff, heat, water, gas, internet, cable television, pool access, fitness facilities, and contributions to reserves. Financing is available with only 10percent down required. An additional benefit for the next owner is the building's current five-year tax moratorium, providing meaningful savings. Monthly assessments are based on $14.82 per share with 115 shares assigned to the unit. Please note that dogs are not permitted. Opportunities to own a high-floor, direct east-facing residence in the legendary Edgewater Beach Apartments are exceptionally rare. Combining breathtaking Lake Michigan views, timeless architecture, full-service amenities, and the enduring character of one of Chicago's most treasured residential buildings, this is a home that can be enjoyed for generations to come.

5555 N Sheridan Road Unit #1612, Chicago

257 E Delaware Place Unit #10AB, Chicago

$1,995,000

4 Beds ⋅ 5 Baths ⋅ 12774015 MLS

Few residences in the Gold Coast offer what discerning luxury buyers value most: an entire floor to themselves, direct private elevator access, exceptional scale, historic character, and the quiet privacy of boutique living. At 257 East Delaware Place, all those qualities come together in one extraordinary penthouse. Set within an elegant 1917 boutique building with just 12 residences, Unit 10AB occupies the entire tenth floor, where a private elevator opens directly into nearly 4,000 square feet of beautifully reimagined living space. Renovated in 2019 with more than $1.2 million in improvements, the home seamlessly blends timeless prewar architecture with sophisticated contemporary design. Oversized arched windows grace the main living spaces, while expansive east-facing windows capture beautiful views of Lake Michigan. Southern and western exposures bathe the residence in exceptional natural light throughout the day. Designed for both grand entertaining and comfortable everyday living, the expansive floor plan features a gracious living room with a rare wood-burning fireplace, a dramatic 25-foot family room, open dining area, and an exceptional chef's kitchen with a 14-foot marble island, Wolf and Sub-Zero appliances, a walk-in pantry, dedicated wine cellar, and wet bar. The private primary suite offers a gas fireplace, dual custom walk-in closets, dressing area, and a spa-inspired marble bath with a Kohler steam shower, NuHeat heated floors, and an oversized soaking tub. Three additional en-suite bedrooms, a powder room, separate laundry room, and dedicated storage complete the residence. Residents also enjoy exclusive access to the building's beautifully landscaped private garden and gazebo an exceptionally rare amenity that provides a peaceful retreat in the heart of the Gold Coast. Just moments away are Oak Street Beach, Lake Michigan, the Magnificent Mile, luxury boutiques, acclaimed restaurants, and Chicago's finest hotels. For those seeking the scale and privacy of a single-family home with the convenience of condominium living, few homes offer the combination of a full-floor layout, boutique ownership, modern luxury, and one of Chicago's most prestigious addresses. Monthly valet parking is available nearby at 200 East Delaware. 257 East Delaware Place is one of the Gold Coast's rarest offerings...a full-floor penthouse that delivers exceptional privacy, timeless architecture, sophisticated design, and an unrivaled lifestyle.

257 E Delaware Place Unit #10AB, Chicago

$285,000

3 Beds ⋅ 2 Baths ⋅ 12773769 MLS ⋅ Harding Court Condos BLDG.

Bring your creative ideas to this sun-filled 3 bedroom duplex offers the space, style, and comfort today's buyers are looking for in the heart of Albany Park. Nicely updated throughout, the home features an open layout ideal for everyday living and hosting, with hardwood floors, 9 foot ceilings, and oversized windows that bring in beautiful natural light. The kitchen is open with sleek cabinetry, granite countertops, and stainless steel appliances, flowing seamlessly into the main living area. Both bathrooms have been tastefully remodeled, and the home has been freshly painted with clean white trim and doors for a crisp, modern feel. Enjoy the convenience of central air, a newer furnace, smart thermostat, in unit washer and dryer, and updated lighting switches, and ceiling fans throughout. The duplex layout provides two full levels of living space, generously sized bedrooms, excellent closet storage, and added flexibility for work or relaxation. Step outside to two private decks, perfect for entertaining, extra storage, or simply unwinding. Located on a quiet, tree lined street close to groceries, restaurants, shopping, and public transportation, this well maintained home offers move in ready living with no immediate projects needed. This property presents a strong opportunity for both homeowners and investors alike. CTA bus 53 at Ainslie/Pulaski & 81 at Lawrence/Pulaski. CTA brown like at Lawrence/Kimball. Easy street parking.

3923 W Ainslie Street Unit #1E, Chicago

$599,000

3 Beds ⋅ 2 Baths ⋅ 12772154 MLS

So much space for the $$$! Stroll to Andersonville, lakefront beaches/trails/dog park, Red Line and more. This pristine home with 29' of east-facing, tree-top views has 9' ceilings, hardwood floors, beautiful millwork and original hardware. Recently updated kitchen has Viking, Miele and Thermador appliances, quartz countertops and glass tile backsplash. Large bedrooms have great closet space - including 2 cedar closets. Lovely bathrooms and central AC via mini-splits. This is one of just 32 homes in the historic 1927 Renaissance. Nearing its 100th anniversary, the Renaissance has been meticulously restored and thoughtfully updated to seamlessly blend the elegance of its 1927 heritage with the luxury and convenience you expect today: fully restored lobby with Butterfly entry system; professionally landscaped grounds on north and south sides of building; on-site engineer and professional management; parking immediately available (2 cars, if needed) with EV charging stations; large, renovated laundry room; 20th floor community room with 360 views. Well-managed association has funded massive improvements in recent years including new freight and passenger elevators. Pet friendly, too!

5510 N Sheridan Road Unit #2A, Chicago

$240,000

1 Beds ⋅ 1 Baths ⋅ 12770958 MLS

Welcome home to Unit 4D at Waveland Court, a gated 1926 courtyard building on one of East Lakeview's most sought-after blocks. This top-floor one-bedroom sits above the treetops, with sunny living room windows looking out over the landscaped courtyard below. The living room is anchored by a true wood-burning fireplace, a rare find that makes Chicago winters something to look forward to. Hardwood floors run through the living room and bedroom. The eat-in kitchen offers warm wood cabinetry, granite counters, a glass mosaic backsplash, stainless steel appliances including a gas range and dishwasher, and a built-in breakfast bar, and it opens onto a private balcony made for morning coffee or evening grilling. The bedroom comfortably fits a queen bed and has generous closet space. The bath features a marble-topped vanity and a full tub with shower. An in-unit washer and dryer, a private walk-in storage locker and a bike room take care of the practical side. Monthly assessments cover heat, gas, water, cable, and building upkeep, which keeps utility bills simple. The building is pet friendly. Parking is available nearby. The location is hard to beat. You are a short walk from the lakefront path, Waveland Golf Course, Montrose and Belmont Harbors, Wrigley Field, and the shops and restaurants of Broadway and Clark. Express buses to the Loop, a Divvy station and quick Lake Shore Drive access make the commute easy. Grocery stores, pharmacies and a fitness center are all within a few blocks. Top-floor light, vintage character and a lakefront address at an accessible price. Schedule your showing today.

636 W Waveland Avenue Unit #4D, Chicago

2915 W Granville Avenue Unit #1E, Chicago

$319,000

3 Beds ⋅ 3 Baths ⋅ 12770338 MLS

Rarely available and hard-to-find spacious duplex in desirable West Rogers Park! This beautifully maintained home offers 3 generously sized bedrooms, 2.5 bathrooms, and the potential for a 4th bedroom in the lower level. The inviting interior features a relaxing Jacuzzi tub, oak kitchen cabinetry complemented by granite countertops, hardwood flooring throughout the main level, and ceramic tile flooring in the lower level. With an abundance of living space, comfort, and desirable features, this exceptional home is ready to impress!

2915 W Granville Avenue Unit #1E, Chicago

$359,900

1 Beds ⋅ 1 Baths ⋅ 12769613 MLS

Experience authentic Chicago loft living in the iconic Green Street Lofts. This light-filled corner one-bedroom blends timeless industrial character with everyday comfort, featuring soaring 13.5-foot timber ceilings, exposed brick, hardwood floors throughout, and two walls of restored industrial windows that flood the home with natural light. As a coveted corner residence, the home enjoys exceptional light and an airy sense of openness rarely found in today's loft market. The open-concept floor plan offers exceptional flexibility for both everyday living and entertaining. The kitchen features maple cabinetry, granite countertops, stainless steel appliances, and generous prep space, while the updated bath showcases classic hexagon tile flooring, white subway tile, and timeless schoolhouse lighting. In-unit laundry, central air, and ample closet space provide modern convenience. The loft-style bedroom preserves the open aesthetic that defines authentic loft living while offering comfortable separation from the main living space, with the flexibility to be fully enclosed if desired. Green Street Lofts is a boutique elevator building ideally positioned in the heart of the West Loop, just moments from Fulton Market, Randolph Street Restaurant Row, Greektown, Mary Bartelme Park, Whole Foods, Mariano's, Union Station, the CTA Blue Line, and some of Chicago's most celebrated dining, shopping, and nightlife. Rich in character, abundant in natural light, and surrounded by one of Chicago's most vibrant neighborhoods, this is a rare opportunity to own an authentic Chicago timber loft where historic architecture and modern city living come together.

400 S Green Street Unit #212, Chicago

747 N Sedgwick Street Unit #4RS, Chicago

$470,000

2 Beds ⋅ 2 Baths ⋅ 12768433 MLS

WOW! You won't find another PENTHOUSE UNIT in such a GREAT LOCATION, a PRIVATE DECK, and Association dues so LOW! This PENTHOUSE UNIT features 3 Amazing levels of living space and is located in the heart of River North! You will immediately notice the Natural Lighting throughout the Home. The Main Level offers an open concept with it's Kitchen/living/dining design, Beautiful hardwood floors, stone-clad wood burning fireplace and vaulted ceilings!!! The Kitchen features beautiful walnut cabinetry, stainless steel appliances, granite countertops and a large breakfast bar. The large second bedroom is on the Main level and has it's own bathroom. The 2nd level offers a massive Loft-Style Primary bedroom (which could easily be converted to a regular enclosed Bedroom) with newer carpeting, tons of storage space, and a bath with a rain shower, and in-unit laundry. The Top/3rd level offers a wet bar and a fridge adjacent to the HUGE PRIVATE roof deck great for Entertaining and enjoying the City Life. This home is steps from everything, including public transportation, highways, grocery, coffee shops, dog parks, fitness studios, and all that River North restaurants and nightlife has to offer! Move-in ready, but your touch could create even more Value! Self-managed and low association costs add significant value, making this an even more desirable home. The possibilities are endless. Set your appointment today.

747 N Sedgwick Street Unit #4RS, Chicago

$240,000

1 Beds ⋅ 1 Baths ⋅ 12764678 MLS

Experience timeless Chicago vintage charm combined with modern comfort in this gorgeous 1-bedroom, 1-bathroom West Town condo. This inviting home showcases stunning original millwork throughout, classic vintage details, and an exquisite original built-in hutch. Designed for flexible living, with separate living and dining rooms. Upgrades include beautifully refinished hardwood floors, fresh paint throughout, new kitchen appliances, and an updated bathroom featuring luxurious new marble flooring. Coin laundry is available in the building, but you may install laundry directly in the unit.

2548 W Augusta Avenue Unit #2R, Chicago

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