View All South Shore Chicago IL Homes with Private Gym Listings

3 Beds ⋅ 2 Baths ⋅ 12745632 MLS ⋅ ACTIVE Status

Sick and tired of cookie cutter remodels.... Well, you've come to the right place! This one is anything but.... This beautifully renovated oversized bungalow in the heart of South Shore is offering the perfect blend of classic Chicago character and modern updates. As a spacious 4-bedroom, 2-bath home, it features over 2,400 square feet of finished living space with thoughtfully designed interiors ideal for both everyday living and entertaining. Step inside to discover gleaming hardwood floors, abundant natural light, and a flowing open-concept layout. The inviting living room showcases a decorative fireplace and seamlessly connects to a formal dining area and updated kitchen complete with stainless steel appliances, modern cabinetry, and ample prep space. The main level offers generously sized bedrooms and a beautifully updated full bath, while the fully finished basement expands your living space with a massive family room, wet bar, additional bedroom, full bath, laundry area, and flexible space perfect for guests, a home office, gym, or media room. Recent improvements include updated mechanicals, central air, newer windows, and contemporary finishes throughout, providing true move-in-ready convenience. Outside, enjoy a private backyard and detached 2-car garage. Located on a quiet, well-maintained block near the lakefront, Lake Shore Drive, The New Obama Center, Jackson Park, South Shore Cultural amenities, shopping, public transportation, and major expressways, this home offers exceptional value and lifestyle in one of Chicago's most rapidly evolving neighborhoods. A must-see South Shore gem combining space, style, and location. Zone B for Homegrown program up to $50k downpayment assistance available.

7707 S Ridgeland Avenue, Chicago

$150,000

3 Beds ⋅ 3 Baths ⋅ 12616115 MLS ⋅ CLOSED Status

Live an enchanted lakefront life in this beautiful 3-bedroom, 3-bath corner unit at the iconic Windsor Beach - a rare blend of 1920's glamour and sophistication. With incredible lakefront views, this unit is spectacular. Designed by renowned architect Robert S. DeGolyer for Chicago's well-heeled families, this coveted "A" tier home offers dramatic views of Lake Michigan from nearly every room. A barrel-vaulted foyer sets a tone of quiet opulence, leading to expansive living and dining rooms where waves from 300 feet of private beach below can be heard through open windows. A private passage leads to two spacious bedrooms, with a third bedroom facing the lake directly. Gleaming hardwood floors, and graceful proportions throughout make this unit an entertainer's dream. One gated parking space is included, and the co-op's monthly HOA covers property taxes, gym, party room, business center, private beach and more. Just minutes from Hyde Park, the University of Chicago, and the future Obama Presidential Center, this exceptional lakefront residence - once featured in Curbed Chicago as an "exceptional value" - offers not only a home, but a lifestyle.

7321 S South Shore Drive Unit #5A, Chicago

$360,000

4 Beds ⋅ 4 Baths ⋅ 12504340 MLS ⋅ CLOSED Status

Fall Special! Welcome to 7537 S Clyde Ave - a beautifully renovated 5-bedroom, 4-bath home in Chicago's vibrant South Shore community. This 1.5 Story residence combines modern design, quality finishes, and a prime location just minutes from Lake Michigan, the upcoming Obama Presidential Library, and downtown Chicago. Step inside to an open-concept main floor featuring a spacious living and dining area that flows into a gorgeous kitchen with quartz countertops, custom cabinetry, and brand-new stainless-steel appliances, including refrigerator, stove, microwave, and dishwasher. Energy efficient washer and dryer are also included for your convenience. The layout offers incredible flexibility, with multiple living areas across all three levels. The lower level is perfect for a family room, game room, or guest suite, complete with a full bathroom and bedroom. Upstairs, the primary suite offers a peaceful retreat with its own elegant bathroom featuring glass shower doors and modern finishes. Two additional bedrooms and another full bath complete this level. The top floor adds two more bedrooms and a full bath, ideal for an office, gym, or additional sleeping quarters. Every detail throughout the home has been updated. The bathrooms are designed with premium materials and glass enclosures, providing a spa-like atmosphere. Outside, enjoy your private yard space, ideal for relaxing or entertaining, with fresh landscaping that enhances the home's curb appeal. Location highlights: just minutes from Lake Shore Drive, Jackson Park Golf Course, the University of Chicago, and the Obama Presidential Center. You'll love being close to the beach, parks, public transit, and downtown Chicago - all within easy reach. Beautifully designed and thoughtfully updated, 7537 S Clyde Ave offers the perfect blend of comfort, style, and convenience. Appliances to be installed a week prior to closing, or sooner. Schedule your private showing today and experience the best of South Shore living!

7537 S Clyde Avenue, Chicago

$620,000

5 Beds ⋅ 4 Baths ⋅ 12491745 MLS ⋅ CLOSED Status

Modern Luxury Meets South Shore Charm - Welcome to 7440 S Oglesby Ave! Step into elevated city living at 7440 South Oglesby Avenue - a bold, design-forward reimagining of the classic Chicago brick bungalow, nestled on a peaceful, tree-lined street in the vibrant South Shore neighborhood. This 5-bedroom, 4-bathroom, nearly 3,000 sq ft home delivers a seamless fusion of timeless architecture and high-end, contemporary finishes. From the moment you walk in, the light-filled open layout welcomes you with soaring ceilings, an eye-catching chandelier, and a sleek fireplace that anchors the living space. The brand-new light oak flooring and modern climate-control windows infuse the home with warmth and energy-efficient comfort. 2-inch white slat blinds provide clean, stylish privacy throughout. At the heart of the home lies a true chef's kitchen - featuring Silestone Miami White quartz waterfall countertops, full-height backsplash, and custom ceiling-height shaker cabinetry with glass-pane accents. A 14-foot center island with a Ruvati 45-inch workstation sink, dual faucets, and seating for six sets the stage for both entertaining and everyday living. The butler's pantry with beverage cooler makes hosting effortless, and a 48-inch, 8-burner gas range anchors the premium stainless steel appliance package. A flexible main-floor bedroom or office, adjacent to a stunning spa-like bath with rainfall shower, adds function and flexibility. Don't miss the thoughtfully designed mudroom and oversized laundry room, fully outfitted with a Samsung front-load washer/dryer, utility sink, and custom organization. Upstairs...two luxe en-suite bedrooms offer the ultimate urban retreat, each with walk-in closets and spa-inspired bathrooms designed for relaxation. The custom staircase, with modern glass panel railings, makes a bold architectural statement as you ascend. The fully finished lower level extends the living space with a large recreation room, two additional bedrooms, a dedicated home gym/flex room, and a beautifully appointed full bath - ideal for guests, extended family, or a live/work setup. Step outside to a private, fenced-in backyard oasis with brand-new landscaping, decorative river rock, and a spacious back deck made for entertaining under the stars. The underground sprinkler system keeps everything lush, while the two-car garage with luxury floor tile offers secure parking and extra storage. For peace of mind, the property is equipped with 5 exterior Arlo security cameras and a Vivint smart security system, with one year of monitoring included. Location? Unmatched. You're minutes from Lake Shore Drive, the lakefront, South Shore Cultural Center, golf courses, parks, museums, Obama Presidential Center, University of Chicago, and the Quantum Computing campus. Enjoy nearby cafes, restaurants, and transit access that connects you seamlessly to downtown and beyond. 7440 S Oglesby isn't just a home - it's a lifestyle upgrade. Come experience modern South Shore living at its finest. BACK ON THE MARKET DUE TO BUYER FINANCING.

7440 S Oglesby Avenue, Chicago

$315,000

2 Beds ⋅ 3 Baths ⋅ 12426098 MLS ⋅ CLOSED Status

Live an enchanted lakefront life in this beautifully redone top floor 2-bedroom, 3-bath corner unit at the iconic Windsor Beach - a rare blend of 1920's glamour and sophistication. With incredible lakefront and City views, this unit is spectacular. Designed by renowned architect Robert S. DeGolyer for Chicago's well-heeled families, this coveted "A" tier home offers dramatic, top-floor views of Lake Michigan from nearly every room. A barrel-vaulted foyer sets a tone of quiet opulence, leading to expansive living and dining rooms where waves from 300 feet of private beach below can be heard through open windows. Impeccably updated by the current owners, the home features renovations including updated bathrooms, a stunning chef's kitchen with granite countertops, stainless steel commercial grade appliances, and abundant cabinetry. Custom millwork includes a beautiful walnut paneled library with recessed wet bar, which could function as a third bedroom. Originally a 3-bedroom unit, the back bedroom was combined with the kitchen to make a spacious gourmet eat-in kitchen. The dining room has a custom hand painted bucolic scene painted on the walls. A private passage lead to two spacious bedrooms and two luxurious bathrooms, thoughtfully positioned for comfort and privacy. Gleaming hardwood floors, and graceful proportions throughout make this unit an entertainer's dream. One gated parking space is included, and the co-op's monthly HOA covers property taxes, gym, party room, business center, private beach and more. Just minutes from Hyde Park, the University of Chicago, and the future Obama Presidential Center, this exceptional lakefront residence - once featured in Curbed Chicago as an "exceptional value" - offers not only a home, but a lifestyle.

7321 S South Shore Drive Unit #12A, Chicago

$268,000

3 Beds ⋅ 2 Baths ⋅ 12368826 MLS ⋅ CLOSED Status

Welcome to this South Shore Gem - a Classic Chicago Bungalow with Timeless Appeal! This spacious 3-bedroom, 2-bathroom brick bungalow features brick exterior construction, an asphalt roof, and warm wood flooring throughout. With generously sized rooms and central air conditioning, this home offers a beautiful display of enduring Chicago craftsmanship. The kitchen includes a dishwasher, and the home is equipped with a Whirlpool water heater for year-round efficiency. The full walk-up basement provides exceptional flexibility-ideal for a home gym, guest suite, or entertainment lounge. An unfinished attic offers even more room for expansion, perfectly suited for a home office, additional bedroom, or creative retreat. Outdoors, a private concrete driveway leads to a spacious backyard-a rare and desirable feature for city living, perfect for relaxing or hosting. Situated near parks, public transit, the lakefront, and local amenities-including the Museum of Science and Industry and the upcoming Obama Presidential Center-7744 S Oglesby Avenue presents a refined living experience in a community rich with culture, history, and promising transformation. Timeless character. South Shore sophistication. Schedule your private showing today-this opportunity won't last.

7744 S Oglesby Avenue, Chicago

$290,000

3 Beds ⋅ 3 Baths ⋅ 12222535 MLS ⋅ CLOSED Status

Welcome to your dream home in South Shore! This spacious 2,700 sq ft, 3-bedroom, one full bathroom with 2 half baths, brick beauty offers a perfect blend of modern amenities, eco-friendly features, and timeless charm. Situated on a peaceful tree-lined street, this home is surrounded by mature trees and features a long driveway leading to a 2-car garage with alley access. Upon arrival, you'll notice the striking red brick exterior, new roof, and solar panels, all complemented by energy-efficient windows that flood the home with natural light. New central air and air handler. All can be controlled away from home with a smart phone. All kitchen appliances new installed in spring 23. Rainwater system installed in 2021. The thermostat controlling the boiler and air conditioning are Echo brand. Step inside to a cozy front room with a wood-burning fireplace and gleaming hardwood floors. The formal dining room is spacious and perfect for entertaining, with a convenient half bath nearby. The heart of the home is the expansive kitchen, featuring brand-new appliances, plenty of counter space, and bright, inviting surroundings. Enjoy your meals in the screened-in back porch, ideal for gatherings with friends and family. The backyard is a nature lover's dream with ample space for outdoor enjoyment. Upstairs, you'll find a full bathroom and three bedrooms, including an adjoining room that can be transformed into a walk-in closet, office, or playroom. The bathroom features a luxurious steam shower. The attic offers a secluded space, perfect for a private retreat, while the fully finished basement provides endless possibilities. It includes a large, open area ideal for a home gym, entertainment room, or additional living space, plus a workshop with a built-in air compressor-perfect for all your DIY projects. This home is ideally located in the desirable South Shore neighborhood, close to Horace Mann Elementary, South Shore College Prep, and excellent public transportation options. Enjoy Rosenblum Park, Jackson Park, the new Obama Presidential Library, and the nearby beach and golf course. This unique property seamlessly combines modern living with nature and convenience. Schedule your private showing today and make this incredible South Shore residence yours! To sweeten the deal, we are offering porch tables, futon in basement, 3 TVs, air compressor stays, kitchen tables and chairs even bunk beds. Let's make this one of kind home yours.

7717 S Bennett Avenue, Chicago

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Homes with Private Gym in South Shore, Chicago IL

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