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7544 S Ridgeland Avenue, Chicago
$499,000
3 Beds ⋅ 4 Baths ⋅ 12803667 MLS ⋅ NEW Status
Beautifully Renovated South Shore Brick Bungalow! This spacious 5-bedroom, 3.5-bath home features two private primary suites, each with its own en-suite bathroom. The main suite offers generous walk-in closet space. Enjoy a modern kitchen, spacious living and dining areas, and a fully finished basement with additional bedrooms, full bath, laundry and recreation space. The home showcases a stunning curved staircase with wood-finish treads, crisp white risers and a decorative railing. Additional highlights include a detached 3-car garage and a flexible layout ideal for multigenerational living. Conveniently located blocks from Jackson Park Hospital, approximately 20 minutes from downtown Chicago, and close to Lake Shore Drive, lakefront beaches and the Obama Presidential Center. Five bedrooms. Two primary suites. Three-car garage. Modern living in a convenient South Shore location!

7544 S Ridgeland Avenue, Chicago

7741 S Yates Boulevard, Chicago
$580,000
9 Beds ⋅ 3 Baths ⋅ 12803520 MLS ⋅ NEW Status
Welcome to this exceptional South Shore three-flat offering timeless Chicago architecture, generous living space, and outstanding investment potential. This classic brick building features three spacious units, each thoughtfully designed with large room sizes, abundant natural light, hardwood flooring, separate dining rooms, and versatile den spaces that can easily serve as home offices, sitting rooms, or additional bedrooms. Rich in vintage character, select units showcase beautiful built-in bookcases and original architectural details that blend seamlessly with tasteful updates. The property is currently producing income with two units occupied, while the vacant third-floor unit presents an outstanding opportunity for an owner-occupant or savvy house hacker to move right in while offsetting their mortgage with rental income from the other two units. For investors, the unit is also being actively marketed for lease, offering the flexibility to bring the building to full occupancy and maximize cash flow. The partially finished basement offers additional usable space and is ready for your finishing touches, creating even more potential to add value. A common-area coin-operated laundry provides an additional income stream, while the detached brick 3-car garage offers valuable parking and the opportunity for supplemental rental income. Completing the property are a rear porch and ample storage, enhancing both functionality and tenant appeal. Ideally situated in the heart of South Shore, you'll enjoy convenient access to Lake Michigan, Rainbow Beach, Jackson Park, the South Shore Cultural Center, the future Obama Presidential Center, Metra and CTA transportation, shopping, dining, parks, and major expressways. Whether you're looking to expand your investment portfolio or take advantage of a rare owner-occupied house hacking opportunity, this is your chance to own a well-maintained, income-producing building in one of Chicago's most historic and steadily revitalizing lakefront neighborhoods. Schedule your private showing today!

7741 S Yates Boulevard, Chicago

6739 S East End Avenue Unit #3, Chicago
$110,000
2 Beds ⋅ 1 Baths ⋅ 12782111 MLS ⋅ NEW Status
Located in South Shore near Jackson Park, this top-floor vintage condo features great natural light, hardwood floors throughout, and a spacious layout with separate living and dining rooms, plus an additional sunroom and bonus room. The two bedrooms are similar in size, offering flexibility in how the space is used, with either room serving as the primary bedroom. Enjoy your own private deck, a shared backyard, and the convenience of off-street parking. Conveniently located near the lakefront and golf course, with easy access to downtown via Lake Shore Drive and close to the Obama Presidential Center. Move right in and make it your own over time, with the opportunity to add your personal style and updates along the way. An appealing opportunity for a first-time buyer or anyone looking for space, character, and a convenient location.

6739 S East End Avenue Unit #3, Chicago

7829 S Marquette Avenue, Chicago
$44,900
4 Beds ⋅ 1 Baths ⋅ 12803030 MLS ⋅ NEW Status
Incredible investment or rehab opportunity in the desirable South Shore neighborhood! This 1.5-story frame/brick home is an unfinished project packed with potential, just waiting for your bright ideas and finishing touches. Featuring 4 bedrooms and 1 bathroom, this spacious layout offers the perfect canvas to design a high-yielding rental or a custom dream home. The property features a full unfinished basement and an expandable attic space, providing endless possibilities for extra living area or storage. Situated on a generous lot with a large yard and a detached 2-car garage. Conveniently located near local schools, parks, shopping, and public transportation options for an easy commute. Property is being sold in "AS IS" condition with no surveys or seller disclosures provided; real estate taxes prorated. Bring your contractor, tools, and vision to unlock this home's true value!

7829 S Marquette Avenue, Chicago

7801 S Phillips Avenue, Chicago
$1,695,000
12778102 MLS ⋅ NEW Status
Discover the investment potential of this three-story brick, 20-unit multifamily apartment building, ideally situated on the southeast corner of 78th Street and Phillips Avenue in Chicago's South Shore neighborhood. Featuring generously sized apartment units, this property offers investors an opportunity to establish rental income, enhance property value, and create long-term cash flow through strategic renovations and property management. The building features solid brick construction, a 2024 steam boiler with new sensors and wireless remote access to control boiler and monitor average temp from phone, state of the art camera system with remote keyless entry, and fully fenced front and rear areas. Spacious apartment layouts offer flexibility for improvements and repositioning to maximize rental potential. LOCATION IS KEY! Conveniently located near Lake Michigan, the South Shore Cultural Center, its nine-hole golf course, neighborhood parks, shopping, dining, and public transportation. The property also provides access to the Obama Presidential Center area and Chicago's broader South Side amenities. Whether you're looking to expand an existing investment portfolio or pursue a value-add multifamily opportunity, this 20-unit Chicago apartment building offers the potential for rental income growth, property improvements such as onsite laundry, and long-term appreciation.

7801 S Phillips Avenue, Chicago

7321 S South Shore Drive Unit #2B, Chicago
$235,000
4 Beds ⋅ 2 Baths ⋅ 12802816 MLS ⋅ NEW Status
Enjoy breathtaking Lake Michigan views from this spacious 4-bedroom, 2-bath Co-Op in Chicago's desirable South Shore area. This beautifully maintained unit features generously sized bedrooms, hardwood floors throughout, a formal dining room, and a versatile library/study that is being used as a 4th bedroom. The updated kitchen offers quartz countertops, stainless steel appliances, and a convenient butler's pantry. In-unit laundry is a rare find in this building, along with abundant closet space and a private storage locker. The assessment includes property taxes, electricity, cable, Wi-Fi, and water. An assigned parking space is available for an additional $50/month. Residents enjoy private beach access along with a meeting room, party room, exercise room, and beach room. With its spacious layout, desirable amenities, and stunning lake views, this is a must-see!

7321 S South Shore Drive Unit #2B, Chicago

7801 S South Shore Drive, Chicago
$2,895,000
12801686 MLS ⋅ NEW Status
PRICE REDUCED for this attractive 1960's era, 32 unit brick building in great location in booming South Shore. Appealing unit mix of 4 studios, 10-1/1's, 15-2/1's and 3-3/1's. Roof, Porches, Masonry/Tuckpointing, and Electrical work done within last 5-8 yrs. Every unit updated with Bath and Kitchen reno during same period. Laundry in basement area and outdoor parking in rear for 16-20 cars. Located 1/2 block from Rainbow Beach Park and Rainbow Beach on the shore of beautiful Lake Michigan. The CTA 26, 6, 71, and N5 buses serve this location with both north and south bound stops at 78th and S. South Shore Dr, and it's just a short 2 block walk to the Metra Line (commuter rail) stop. Less than 3 miles to world renowned University of Chicago, the new Obama Presidential Library, the soon to be renovated Jackson Park Golf course, and just 9 blocks from the Campus of the soon to be built, 1 million s.f. Illinois Quantum and Microelectronics Park. Also, less than 11 miles to the center of downtown Chicago. New property management is in place and is working to stabilize rents.

7801 S South Shore Drive, Chicago

7850-7851 S Constance Avenue, Chicago
$245,000
12801337 MLS ⋅ NEW Status
UNLIMITED POTENTIAL & MASSIVE VALUE-ADD OPPORTUNITY IN PRIME SOUTH SHORE! Heavy-hitting investment package featuring a 31-unit mixed-use building in a rapidly developing neighborhood. Fantastic scale with 28 residential units (24 studios and 4 one-bedroom apartments) plus 3 street-level commercial retail spaces offering high visibility and foot traffic. Perfect for an experienced investor or developer looking to execute a full renovation, add value, and stabilize for maximum cash flow or long-term portfolio growth. Conveniently situated near public transportation, major thoroughfares, shopping, and lakefront amenities. Property needs work and is being sold in AS-IS / WHERE-IS condition. Seller will not provide surveys or disclosures; real estate taxes will be prorated. Bring your vision to unlock this property's true potential!

7850-7851 S Constance Avenue, Chicago

2772 E 75Th Street Unit #5BSW, Chicago
$170,000
2 Beds ⋅ 2 Baths ⋅ 12791492 MLS ⋅ NEW Status
Take in beautiful views of Lake Michigan and the surrounding park from this inviting 5th-floor, 2-bedroom, 2-bath condo in Chicago's South Shore neighborhood. This residence offers a comfortable layout with a spacious living and dining area, ideal for everyday living and entertaining. Recent updates include modern appliances and refreshed recessed lighting including an updated bathroom, adding a clean, contemporary touch. The primary bedroom features a custom closet and private en-suite bath, while the second bedroom offers flexibility for a guest room, home office, or additional personal space. Enjoy the convenience of being near the lakefront, private beach access, public transportation, neighborhood schools, cultural destinations, and the historic South Shore Country Club. With its elevated views, practical floor plan, and desirable location, this condo is a wonderful opportunity for both homeowners and investors seeking to enjoy all that South Shore has to offer.

2772 E 75Th Street Unit #5BSW, Chicago

6723 S Euclid Avenue, Chicago
$614,900
4 Beds ⋅ 3 Baths ⋅ 12793994 MLS ⋅ ACTIVE Status
Located in historic Jackson Park Highlands, this spacious 4-bedroom, 2.5 -bath home is filled with character, personality, and room to truly LOVE WHERE YOU LIVE. Some homes are simply properties. Others carry history, memories, and a legacy that deserves to continue. For more than 40 years, this home has been owned by the same family, and now it is ready for its next chapter. From the dedicated study and formal dining room to the family room designed for gathering, this home gives you space to live, work, entertain, and create new memories. And then there's the additional room that once served as the home's hot tub room. Yes, a dedicated hot tub room. Bring your vision and reimagine the space as a wellness room, home gym, creative studio, lounge, or something completely your own. Need even more space? The home also features a fully unfinished basement with a dedicated laundry area, offering additional room for storage and the opportunity to explore future possibilities based on your needs and vision. Come in. Walk the home. See the character. Imagine the possibilities. With minor upgrades, thoughtful improvements, and your personal touch, this property offers the opportunity to create a home that reflects your style and how you want to live. Jackson Park Highlands is known for its distinctive architecture, beautiful homes, tree-lined streets, and rich history. You're also minutes from Jackson Park, Chicago's lakefront and beaches, the Museum of Science and Industry, golf, DuSable Lake Shore Drive, and the Obama Presidential Center. After more than four decades of one family's memories, this home is ready for a new story, a new vision, and a new legacy. This home SCREAMS: LOVE WHERE YOU LIVE. Ready to walk it? Let's get you inside.

6723 S Euclid Avenue, Chicago

7144 S Bennett Avenue, Chicago
$217,000
10 Beds ⋅ 3 Baths ⋅ 12798671 MLS ⋅ ACTIVE Status
THE LOT. THE LOCATION. THE UPSIDE. Welcome to 7144 S Bennett Avenue, a substantial three-story brick three-flat in Chicago's South Shore neighborhood, situated on an impressive 50 x 135 oversized lot. Featuring a reported 10 bedrooms, 3 bathrooms, a full basement, and garage parking, this property offers the scale and potential experienced investors look for. Near Jackson Park, Lake Michigan, public transportation, and the Obama Presidential Center, the location adds another compelling reason to take a closer look. A BIG PROJECT WITH BIG POTENTIAL! Restore, reposition, and explore the possibilities of this classic Chicago multifamily property. Extensive rehabilitation required. Known building violations and structural concerns exist. Sold strictly AS-IS. Buyer to verify condition, legal use, and renovation feasibility. Bring your contractor. Run your numbers. Schedule your showing today!

7144 S Bennett Avenue, Chicago

7712 S Ridgeland Avenue, Chicago
$260,000
6 Beds ⋅ 4 Baths ⋅ 12797733 MLS ⋅ PRICE CHANGE Status
***ACCEPTING CASH OFFERS!!!! BUYER COULDN'T GET FINANCED. Will not pass FHA inspection. Mold present in the basement.*** Majestic beautiful legal 4 flat on serene tree lined street. These 3 units of 2 bed/1 bath have the largest footprint in all of South Shore!!! These are regal sun drenched units with huge formal living room, separate formal dining room, breakfast nook off the kitchen with walk-in pantry, 2 massive oversized bedrooms, and fabulous long hallways that make the perfect gallery for art or family photos!!! Hardwood floors throughout!!! Units are so oversized, you can easily add a 3rd bdrm and another full bath. Full unfinished english basement large enough for an additional 2 or 3 bedroom unit, lovely cemented backyard and a 3 car garage!!! Entry reception hall into each unit with glass door enclosed built-in bookshelves. Regal building entry vestibule that's large enough to hold 30 people comfortably. Amazing spaces!!! Updates needed throughout. AS-IS! Mold present in basement. ****Must sign hold harmless prior to viewing!!!!

7712 S Ridgeland Avenue, Chicago

7228 S Ridgeland Avenue, Chicago
$279,900
5 Beds ⋅ 2 Baths ⋅ 12797608 MLS ⋅ ACTIVE Status
WELCOME TO THIS IMPRESSIVE, FULLY UPDATED AND SPACIOUS HOME OFFERING THE PERFECT COMBINATION OF MODERN STYLE, COMFORT, AND FUNCTIONALITY! FEATURING 5 GENEROUSLY SIZED BEDROOMS AND 2 FULL BATHROOMS, THIS BEAUTIFULLY UPDATED HOME OFFERS PLENTY OF SPACE TO LIVE, RELAX, AND ENTERTAIN. STEP INSIDE TO DISCOVER GORGEOUS HARDWOOD FLOORS, A BRIGHT AND EXPANSIVE LIVING ROOM WITH AN ELEGANT FIREPLACE, ABUNDANT NATURAL LIGHT, AND A SEPARATE DINING AREA PERFECT FOR GATHERINGS. THE MAIN LEVEL FEATURES 3 SPACIOUS BEDROOMS, A FULL BATHROOM, AND THE CONVENIENCE OF MAIN-LEVEL LAUNDRY. THE SECOND LEVEL OFFERS 2 ADDITIONAL GENEROUSLY SIZED BEDROOMS AND A SECOND FULL BATHROOM, PROVIDING FLEXIBLE LIVING OPTIONS. THE FINISHED ATTIC ADDS VALUABLE LIVING SPACE, WHILE THE UNFINISHED BASEMENT OFFERS ENDLESS POSSIBILITIES FOR STORAGE OR FUTURE CUSTOMIZATION. WITH ITS GENEROUS LAYOUT, MODERN UPDATES, AND VERSATILE LIVING SPACES.

7228 S Ridgeland Avenue, Chicago

1708 E 73Rd Street, Chicago
$194,900
2 Beds ⋅ 2 Baths ⋅ 12796296 MLS ⋅ ACTIVE Status
Welcome home to this beautifully maintained South Shore gem! Fully rehabbed in 2019 and meticulously cared for by the seller, this home offers two generously sized bedrooms and 1.5 bathrooms. Hardwood flooring throughout and beautiful staircase spindles add warmth and character, while the kitchen features quartz countertops, rich dark cabinetry, and stainless steel appliances. The finished basement provides additional space for entertaining, hosting your next Chicago Bears watch party, or relaxing at home, complete with a bathroom and dedicated laundry room. With public transportation and schools within walking distance, this move-in-ready home offers comfort, style, and convenience. Schedule your showing today! Sold As-Is Where-Is

1708 E 73Rd Street, Chicago

7601 S Kingston Avenue, Chicago
$1,900,000
12797042 MLS ⋅ ACTIVE Status
Pleased to exclusively present this large corner courtyard building located in the heart of Chicago's South Shore neighborhood. This attractive investment opportunity features a desirable unit mix consisting of 12 studios, 13 one bedroom units, and 9 spacious two bedroom units. These fully renovated units are achieving top of the market rents on the block. The owners have put in a new boiler (2025), New roof, porches, and tuckpointing (2026), and skilled renovation projects to the units that turnover. Ideally situated within walking distance to Windsor Park Metra Station and CTA buses, this property enhances tenant convenience and appeal. Nearby attractions include Rainbow Beach, the South Shore Cultural Center, the new The Obama Presidential Center, and the picturesque Lakefront.

7601 S Kingston Avenue, Chicago

7649 S Luella Avenue, Chicago
$519,999
4 Beds ⋅ 3 Baths ⋅ 12796471 MLS ⋅ ACTIVE Status
Welcomes to south shore's newest GEM!! Rarely available remodeled Bungalow with a side lot included!! This beautiful home features 6 bedrooms, 3 baths, and an astonishing finished basement! As you enter you will come across beautiful Greek coffered ceilings and an alluring living room fireplace. Next you have 3 bedrooms followed by a huge full charming bathroom with tile around! Next you will enter the royal dining room next to the kitchen of your dreams! 42 inch cabinets, crown molding, led lighting, quartz countertops, and stainless steel appliances! Up to the second floor you will find a one of a kind primary bedroom with its own full bath! Bedroom is huge and has a walk in closet! Bathroom is huge and includes a freestanding tub, separate shower, fireplace, and tile all around!! There are skylights all throughout the second floor for added sunlight and relaxing rainy nights! Down to the lower level you will encounter a marvelous flooring design followed by a massive fireplace, 2 bedrooms, and another full bath!! On the exterior you will have it like no other! TWO LOTS!! A one of a kind opportunity to own a soccer field! Huge family BBQ hostings, or simply build yourself another house!! Endless possibilities!!! In addition home presents a brand new fence, new siding, and brick two car garage! Home is located on a beautiful and quiet tree line street! You won't find another opportunity like this! Schedule your showing today!

7649 S Luella Avenue, Chicago

7719 S Merrill Avenue, Chicago
$309,900
3 Beds ⋅ 3 Baths ⋅ 12795004 MLS ⋅ ACTIVE Status
Looking for a gorgeous, just-rehabbed home in red-hot South Shore with great room sizes & curb appeal? Then come see this stunning brick tri-level home, which features 4 bedrooms & 2 1/2 bathrooms, on a beautiful, quiet block. The 1st floor is open & spacious, with gleaming hardwood floors & tons of light, & features the living room, kitchen, dining room, and a 1/2 bath. The gorgeous chef's kitchen boasts brand-new, higher-end stainless steel appliances, a granite counter top, tile back splash, & 42" soft-touch shaker cabinets. The upper level features 3 large bedrooms with plus-sized closets, & a full bath. The basement features the 2nd full bathroom, the 4th bedroom, a large family room, & a laundry room that includes a storage area. Out back is a huge back yard, & a large side yard features a brand-new outdoor patio. Professional landscaping, tuck pointing, new roof, a sump pump & ejector pump for flood control, all new central heating, central air, electrical, plumbing etc. - too much to list! This is truly a must see!

7719 S Merrill Avenue, Chicago

7617 S Crandon Avenue, Chicago
$389,000
3 Beds ⋅ 2 Baths ⋅ 12794050 MLS ⋅ ACTIVE Status
This one checks the boxes people are looking for - space, updates, a finished basement, and a brand-new 2.5-car garage. With 4 bedrooms and 2 full baths, this home has been renovated from top to bottom with new windows and doors, new flooring, fresh paint, electrical updates with a new subpanel, new A/C, an updated kitchen with new cabinetry and appliances, and refreshed bathrooms including a new upstairs tub and downstairs shower. The finished basement gives you even more room to spread out, entertain, work from home, or create the extra space you've been needing. Fully electric, move-in ready, and located near Lake Michigan, parks, shopping, dining, and transportation - homes with this many updates already completed do not come around often.transportation, and Lake Michigan, this is a turn-key home with extensive improvements already completed.

7617 S Crandon Avenue, Chicago

3017 E 78Th Street Unit #3A, Chicago
$75,000
1 Beds ⋅ 1 Baths ⋅ 12792870 MLS ⋅ ACTIVE Status
Welcome home to this charming 1-bedroom, 1-bath co-op, where vintage character and thoughtful updates create a warm, inviting space. Abundant natural light highlights the beautiful hardwood floors, while the comfortable layout offers space to relax and make yourself at home. Updated in late 2020, this bright residence includes all appliances for added convenience. Enjoy nearby Rainbow Beach Park and the shores of Lake Michigan, with access to scenic walking and biking paths, tennis courts, and lakefront recreation. Area destinations include the Griffin Museum of Science and Industry, Jackson Park Golf course, and the Obama Presidential Center, along with the Quantum Shore Chicago development at the former U.S. Steel South Works site. Monthly assessments include property taxes, heat, cooking gas, water, and building maintenance. Additional amenities include on-site laundry, private storage, and permit parking. Purchase is subject to co-op board approval. A lovely opportunity to enjoy vintage charm and everyday convenience near Chicago's lakefront!

3017 E 78Th Street Unit #3A, Chicago

7719 S Oglesby Avenue, Chicago
$130,000
3 Beds ⋅ 1 Baths ⋅ 12792092 MLS ⋅ ACTIVE Status
Classic brick bungalow in Chicago's South Shore offering an excellent opportunity for renovation and value-add potential. This property features 3 bedrooms, 1 bathroom, a finished attic with 2 additional rooms, and a large finished basement. The main level offers separate living and dining rooms, a cozy sunroom, a spacious kitchen, and original hardwood flooring in good condition. Large front windows provide abundant natural light, while the rear porch adds to the home's classic character. Situated on Oglesby Avenue, a street known for its historic Chicago brick architecture, this property offers charm, solid bones, and an opportunity to restore its original appeal. Ideal for investors seeking their next rehab project or buyers looking to customize a home to their vision. Property is being sold as a renovation opportunity. Buyer to perform due diligence regarding property condition, room use, and renovation requirements.

7719 S Oglesby Avenue, Chicago



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