Far South Chicago Homes with Vintage Style

Welcome to Far South Chicago, a vibrant neighborhood that beautifully marries rich history with modern living. Nestled within Cook County, this charming area offers a unique blend of vintage homes and contemporary amenities, making it an ideal place for those who appreciate character and community.

Far South Chicago is known for its stunning vintage-style homes that reflect the architectural elegance of a bygone era. Many residences feature intricate woodwork, spacious porches, and classic brick facades that tell stories of the past. Whether you’re drawn to the grandeur of a historic Victorian or the cozy charm of a Craftsman bungalow, you’ll find a variety of options that exude warmth and charm. These homes not only offer aesthetic appeal but also provide a sense of stability and continuity in a rapidly changing city.

Beyond the beautiful homes, Far South Chicago boasts a strong sense of community. Residents enjoy access to local parks, schools, and a supportive neighborhood atmosphere. The area is also rich in cultural history, with numerous community events, art fairs, and local markets that bring neighbors together.

With convenient access to public transportation and major highways, commuting to downtown Chicago or beyond is a breeze, making Far South Chicago an appealing choice for both families and professionals.

Discover the allure of vintage-style homes in Far South Chicago, where history meets community, and every street has a story waiting to be told. Embrace the charm of this remarkable neighborhood and find your perfect home today!

Newest Far South Chicago Homes with Vintage Style

$180,000

1 Beds ⋅ 1 Baths ⋅ 12707351 MLS ⋅ ACTIVE Status

Welcome to 5551 S. Kimbark Ave., a sun-filled 2nd floor condo offering vintage charm in one of Hyde Park's most sought-after locations. This spacious one-bedroom, one-bath residence features hardwood floors, abundant natural light, generously sized rooms, a dining area, radiant heat, private storage, bike storage, and convenient on-site laundry. The kitchen blends classic character with modern touches, featuring quartz countertops, subway tile backsplash, and refreshed cabinetry. Residents enjoy a beautifully landscaped courtyard that creates a peaceful retreat in the heart of the city while being just moments from the University of Chicago, the Laboratory Schools, the Museum of Science and Industry, the Obama Presidential Center, Jackson Park, Promontory Point, and 57th Street Beach. Everyday conveniences are just around the corner with Trader Joe's, Whole Foods, Target, the vibrant 53rd and 55th Street shopping districts, neighborhood coffee shops, restaurants, bakeries, fitness centers, and the popular 61st Street Farmers Market. Commuting is effortless with nearby CTA bus routes, the Metra Station, and easy access to Lake Shore Drive, placing downtown Chicago just minutes away. Whether you're searching for your first home, a University of Chicago residence, or simply want to experience the Hyde Park lifestyle, this charming condo offers an exceptional combination of character, convenience, and location. Schedule your tour today!

5551 S Kimbark Avenue Unit #14, Chicago

$240,000

2 Beds ⋅ 2 Baths ⋅ 12694530 MLS ⋅ ACTIVE Status

1209 E 53Rd Street Unit #1, Chicago

$119,900

1 Beds ⋅ 1 Baths ⋅ 12700676 MLS ⋅ ACTIVE 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 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

$419,500

3 Beds ⋅ 2 Baths ⋅ 12699512 MLS ⋅ ACTIVE 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

$925,000

5 Beds ⋅ 4 Baths ⋅ 12677119 MLS ⋅ ACTIVE Status

Rarely does an opportunity like this come along in the heart of Hyde Park. Located just a few doors from the University of Chicago Laboratory Schools and moments from the University of Chicago campus, this extraordinary penthouse residence offers an unmatched combination of space, character, and convenience. Created by combining two top-floor condominiums into one spectacular home, this expansive residence lives like a single-family home while offering the ease of condominium living. With five bedrooms and three full baths, the thoughtfully designed floor plan provides incredible flexibility for everyday living, working from home, and entertaining. The beautiful and bright kitchen features abundant cabinetry, generous prep space, and extensive counter seating that invites family and friends to gather. A gracious living room and a huge library provide inviting spaces to relax or work, while the stunning primary suite includes a remarkable dressing room and tons of built-in storage rarely found in city living. Vintage charm abounds throughout, with beautiful original details, elegant millwork, and multiple fireplaces adorned with unique antique tile surrounds that add warmth and distinction to the home. Step outside to enjoy the expansive rear deck spanning the entire width of the building-an exceptional outdoor retreat with ample space for dining, gardening, and entertaining. Completing this remarkable offering are in-unit laundry, basement storage and two exterior parking spaces, an invaluable convenience in this sought-after neighborhood. Perfectly positioned near the University of Chicago, the Obama Presidential Center, neighborhood parks, acclaimed dining, shopping, and public transportation, this truly one-of-a-kind Hyde Park penthouse offers the very best of historic character and modern city living.

5738-40 S Kenwood Avenue Unit #3, Chicago

$270,000

2 Beds ⋅ 1 Baths ⋅ 12689453 MLS ⋅ ACTIVE Status

Welcome to a one of a kind vintage co-op in the heart of historic Hyde Park. Flooded with natural light this 2 bed/1 bath charming top floor home boasts oak hard wood floors, original doors and hardware, built in bookcases, and beautiful crown moldings. The living room and dining room seamlessly flow together providing ample space for entertaining. A newer kitchen showcases stainless steel appliances and a butler pantry. Private washer and dryer accessible in the basement. Plenty of nearby dining and shopping options, and easy access to public transportation. Steps to the University of Chicago with all it has to offer, and only a short walk to the Obama Center campus. Property taxes included in HOA dues. This is an extremely well run co-op that should not be missed.

1419 E 58Th Street Unit #3W, Chicago

$249,000

2 Beds ⋅ 1 Baths ⋅ 12683114 MLS ⋅ ACTIVE Status

Welcome to the heart of Hyde Park and all it has to offer. This fully-renovated coop unit is conveniently located on the first floor of a charming corner vintage building just steps from University of Chicago and the U Chicago Medical Center. The quiet park-front setting has three living/dining room bay windows and the two kitchen windows right on Stout Park bringing light and green into the whole apartment. The bedrooms, living/dining room, and hallway boast hardwood floors and original preserved moldings throughout. The unit's complete gut renovation includes an all new kitchen with a dishwasher, quartz counters and marble porcelain floors, a new designer bathroom with a vented ceiling fan with heat, new windows with window treatments, all new electric, all new plumbing, new lighting and ceiling fans, and a new walk-in linen closet with a vented full-sized stacked washer/dryer. Savor quiet moments in the cozy bright sunroom, or take in the views from the park-front deck and enjoy the green space of Florence Stout Park as your own backyard. A private storage room is also included. As an added perk, furniture is being offered with the unit.

5463 S Ellis Avenue Unit #1, Chicago

$275,000

2 Beds ⋅ 1 Baths ⋅ 12679516 MLS ⋅ ACTIVE Status

Fabulous building in the Golden Rectangle area of Hyde Park. In unit washer and dryer! This sundrenched condo features a unique skylight and beautiful natural light throughout. The open floor plan highlights natural woodwork, including a custom-built hutch, a decorative fireplace, and a barn door in the living room/second bedroom. The kitchen offers ample counter and cabinet space and opens to a private outdoor patio deck. The spacious living room is currently configured as a second bedroom. Located just steps from the Metra, CTA, and the Museum of Science and Industry, this home offers exceptional convenience. Close to Lake Michigan, Trader Joe's, bookstores, restaurants, and the University of Chicago Lab School, University of Chicago campus. The building includes shared outdoor patio space, and street parking is readily available in the area.

1446 E 56Th Street Unit #3, Chicago

$220,000

4 Beds ⋅ 3 Baths ⋅ 12661508 MLS ⋅ ACTIVE Status

Welcome to Residence 6A at 6700 S. Crandon Avenue - a beautifully appointed 4-bedroom, 2.5-bath home offering timeless elegance in one of Chicago's classic vintage buildings. This spacious residence blends gracious architectural details with exceptional lake and golf course views, creating a truly exceptional living experience. Step through a semi-private elevator lobby into a grand entry gallery that sets the tone for the home's sophisticated character. The expansive floor plan features four generously sized bedrooms, a separate formal dining room ideal for entertaining, and abundant natural light throughout. Enjoy picturesque views of Lake Michigan and the golf course from the comfort of your home, all while living in a full-service building with a doorman and classic vintage charm. Perfectly situated just steps from the lakefront, parks, and walking paths, this residence offers both tranquility and convenience. Located minutes from Downtown, the Obama Presidential Library, and the Museum of Science and Industry, all via DuSable Lake Shore Drive. This remarkable home combines space, elegance, and an unbeatable location in the heart of South Shore. Credit at Closing for Dishwasher.

6700 S Crandon Avenue Unit #6A, Chicago

$109,900

1 Beds ⋅ 1 Baths ⋅ 12656796 MLS ⋅ ACTIVE 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

$340,000

3 Beds ⋅ 2 Baths ⋅ 12563113 MLS ⋅ ACTIVE Status

1327 E 52Nd Street Unit #302, Chicago

$259,900

3 Beds ⋅ 3 Baths ⋅ 12639863 MLS ⋅ ACTIVE Status

Positioned high above the shoreline in the iconic Windsor Beach, this elegant 7th-floor residence offers breathtaking east and southeast views of Lake Michigan from one of South Shore's most distinguished historic buildings. Rich in architectural character, the home features graciously scaled rooms, hardwood floors, refined moldings, and a dramatic barrel-vaulted foyer that evokes timeless 1920s sophistication. Wake to sunrises over the lake and enjoy the soothing sound of waves from the private residents-only beach below. Windsor Beach delivers a true luxury lifestyle with 24-hour door staff, fitness center, sundeck, gated parking, private beach access, bike/storage rooms, and beautifully maintained grounds. Ideally located near the South Shore Cultural Center, Jackson Park Harbor, the future Obama Presidential Library Center, Jackson Park/South Shore Cultural Center golf courses, dining, and Lake Shore Drive-offering an exceptional blend of historic elegance, lakefront serenity, and city convenience just minutes from downtown Chicago. Pet-friendly. Over 2200 sq. ft. of living area!! Close to several public beaches, bike trails, jogging paths and beautiful parks... You're going to LOVE it!

7321 S South Shore Drive Unit #7B, Chicago

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