Chi - Greater Grand Crossing Homes under $500,000

Welcome to Greater Grand Crossing, a vibrant neighborhood nestled in the heart of Chicago, Illinois. Known for its rich history and diverse community, Greater Grand Crossing offers a unique blend of urban living and suburban charm. This area is characterized by its tree-lined streets, beautiful parks, and a strong sense of community, making it an ideal place for families, young professionals, and anyone looking to enjoy the best of city life.

One of the standout features of Greater Grand Crossing is its affordability. With a variety of homes available for under $500,000, this neighborhood presents an incredible opportunity for first-time homebuyers and investors alike. From charming single-family homes to modern townhouses, the real estate options cater to a range of tastes and budgets. Imagine settling into a cozy abode with a backyard for summer barbecues or a stylish condo with easy access to public transportation and local amenities.

The community is also home to several parks, including the lovely Grand Crossing Park, where residents can enjoy recreational activities, picnics, and community events. The area boasts a rich cultural scene, with local shops, restaurants, and markets that reflect the neighborhood's diversity.

With its affordable housing options, strong community spirit, and convenient location, Greater Grand Crossing is a hidden gem in Chicago. Whether you’re looking to invest in your first home or seeking a welcoming community to grow in, this neighborhood has something special to offer. Come explore the possibilities and discover your new home in Greater Grand Crossing!

Newest Chi - Greater Grand Crossing Homes under $500,000

$266,999

4 Beds ⋅ 4 Baths ⋅ 12778989 MLS ⋅ NEW Status

Welcome to this COMPLETELY RENOVATED home where EVERYTHING IS BRAND NEW! Featuring 4 spacious bedrooms, 3.5 stunning bathrooms, and a bright, open-concept layout, this home was thoughtfully redesigned with modern style and quality craftsmanship throughout. Enjoy the peace of mind that comes with a NEW ROOF, NEW FURNACE, NEW A/C UNIT, NEW HOT WATER TANK, and countless additional upgrades from top to bottom. The expansive finished basement provides the perfect space for entertaining, a home theater, recreation room, home office, or guest accommodations. The luxurious primary suite offers a beautifully designed en-suite bathroom and direct access to a private patio, perfect for enjoying your morning coffee or relaxing at the end of the day. Conveniently located near parks, shopping, restaurants, public transportation, and major expressways, this MOVE-IN READY home is the perfect combination of comfort, style, and convenience. Don't miss your opportunity to make this exceptional home yours!

7116 S University Avenue, Chicago

$449,000

6 Beds ⋅ 3 Baths ⋅ 12778692 MLS ⋅ NEW Status

Beautifully updated two-unit building in Chicago's desirable Woodlawn neighborhood, offering an excellent opportunity for both investors and owner-occupants. This well-maintained property features spacious units, modern updates, and flexible living arrangements. The duplexed-down main-level unit offers 4 large bedrooms and 2 full baths, while the upper-level unit features 3 bedrooms and an updated full bath. Both units offer bright, inviting living spaces, generous bedrooms, ample storage and renovated finishes throughout. The refreshed eat-in kitchens feature breakfast nooks, newer cabinetry, modern quartz countertops, stainless-steel appliances, and custom tiled backsplashes creating a clean, contemporary feel. Large windows fill the units with natural light, while updated flooring throughout adds to their move-in appeal. Classic Chicago architecture blends seamlessly with modern updates, creating a property that is both charming and practical. Ideally located near public transportation, parks, shopping, restaurants, and major roadways, this property provides convenient access to surrounding neighborhoods and downtown Chicago. Its proximity to the University of Chicago, Jackson Park, and the Obama Presidential Center further enhances its appeal. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this versatile property is an opportunity worth exploring.

7026 S Eberhart Avenue, Chicago

$379,000

3 Beds ⋅ 3 Baths ⋅ 12778381 MLS ⋅ NEW Status

7719 S Rhodes Avenue, Chicago

$259,000

3 Beds ⋅ 3 Baths ⋅ 12777748 MLS ⋅ NEW Status

Welcome Home! This 2 Story 3Bed/2.5Bath Home is Waiting For Your Family. First Floor Features an Open Concept Living & Dining Area with Big Bay Windows for Plenty of Natural Sunlight. Boutique Inspired Powder Room for Guest. Kitchen is Nicely Appointed with Stainless Steel Appliances, New Quartz Countertops & Breakfast Bar. Refinished Hardwood Steps Lead You Upstairs to 3 Bedrooms & Bathroom with Floating Sink & Double Shower Head. Finished Basement Has Ample Space for Entertaining, Washer/Dryer & an Additional Full Bathroom. 2 Car Parking Pad Located in the Rear with Privacy Fence. This Home Shows Owners Pride with Many 2022 Updates that Include, New Roof, New Paint, Refinished Hardwood Floors, New Central A/C (2020), Furnace & Water Heater (5 years old) Refrigerator (2026) & Newer Washer/Dryer. Make Your Appointment Today!

7803 S Champlain Avenue, Chicago

$199,000

3 Beds ⋅ 2 Baths ⋅ 12777697 MLS ⋅ NEW Status

This attractive and spacious home! The house features three bedrooms, one full bathroom, dining room, new windows, new decor, full basement with additional bedrooms and full bathroom, appliances, large rear yard with privacy fence, two car detached garage!

7644 S Champlain Avenue, Chicago

$424,900

5 Beds ⋅ 4 Baths ⋅ 12777109 MLS ⋅ NEW Status

Beautifully updated and luxurious 5-Bed/4-Bth home offering over 4,500 sq ft of finished living space! Recently rehabbed, this stunning home combines sophisticated design with modern comfort and is truly move-in ready. Step inside to an expansive living and dining area featuring an elegant statement wall and coffered ceilings that create an elevated first impression. The gorgeous kitchen is the heart of the home, showcasing crisp white cabinetry, stainless steel appliances and an oversized island with breakfast bar. Two spacious bedrooms and full bath complete the main level. Upstairs, the luxurious Primary Suite offers a private retreat with generous living space, walk-in closets and a beautiful en-suite bath. Two additional bedrooms and another updated full bath provide plenty of space for family and guests. The finished basement expands the living space even further with a large recreation room, custom wet bar and the home's fourth full bath. No detail was overlooked in this comprehensive renovation, with updates including a new roof, windows, A/C, water heater, appliances, plumbing, electrical, ductwork and more. With its high-end finishes, thoughtful layout and impressive amount of living space, this exceptional home offers the perfect blend of luxury, style and functionality. Schedule your private tour today! *Seller is open to reviewing all offers and terms*

7801 S Eberhart Avenue, Chicago

$199,900

3 Beds ⋅ 2 Baths ⋅ 12776714 MLS ⋅ NEW Status

WELCOME HOME! Come take a look at this beautifully updated 3-bedroom, 2.5-bath single-family home featuring a spacious layout, modern finishes, and plenty of room for comfortable living. The main level welcomes you with a bright living room featuring beautiful hardwood floors, a formal dining room with matching hardwood flooring, and a fully updated kitchen with white Shaker-style cabinets, ample storage, and a clean, modern look. The main floor also includes an upgraded half bath, along with new doors and trim throughout the home. Upstairs, you'll find two generously sized bedrooms with ample closet space and a fully updated full bathroom. The lower level offers even more living space with a large family room, laundry room, and utility room, plus convenient exterior access to the spacious backyard-perfect for entertaining, relaxing, or enjoying outdoor activities. With its thoughtful updates, functional floor plan, and generous living space, this home is ready for its next owner. Don't miss the opportunity to make this your next home-schedule your showing today!

7645 S Drexel Avenue, Chicago

$339,500

4 Beds ⋅ 3 Baths ⋅ 12776756 MLS ⋅ NEW Status

ABSOLUTELY STUNNING RECENTLY REHABBED FIVE BEDROOM HOME JUST MINUTES AWAY FROM 90/94 AND WALKING DISTANCE TO SHOPPING, RETAIL, SCHOOLS, PARKS, AND ALL THAT THE AREA HAS TO OFFER. THE MAIN LEVEL OF THIS METICULOUSLY MAINTAINED HOME FEATURES AN OPEN CONCEPT LIVING ROOM/DINING ROOM, UPDATED KITCHEN WITH AMPLE CABINET AND COUNTERTOP SPACE, TWO SPACIOUS BEDROOMS, AND FULL BATH. THE UPSTAIRS INCLUDES THE PRIMARY SUITE FEATURING A HUGE WALK-IN CLOSET/SITTING ROOM, FULLY REHABBED SHARED BATH, AND ADDITIONAL OVERSIZED BEDROOM. THE LOWER LEVEL OF THIS GEM INCLUDES A MASSIVE DEN/LIVING ROOM, ADDITIONAL BEDROOM WITH WALK-IN CLOSET, FULL BATH WITH BEAUTIFUL FULLY TILED SHOWER, ADDITIONAL STORAGE SPACE, AND LAUNDRY AREA. THIS HOME ALSO FEATURES UPDATED PLUMBING, ELECTRICAL, HVAC, NEWER DECK/PORCH, AND TWO CAR GARAGE.

7643 S Eberhart Avenue, Chicago

$435,000

7 Beds ⋅ 2 Baths ⋅ 12747469 MLS ⋅ NEW Status

Welcome to 7322 S Langley Ave! Situated on a desirable **double lot** in Chicago's Greater Grand Crossing neighborhood, this updated 2-unit property offers space, versatility, and excellent investment potential. First floor unit features 3 bedrooms and 1 bathroom with access to additional finished lower-level space. Second Floor unit features 4 bedrooms and 1 bathroom. Both units are vacant, providing flexibility for owner-occupants and investors alike. Enjoy the expansive outdoor space, a neighborhood elementary school directly across the street, and convenient access to public transportation, shopping, and local amenities. An attractive opportunity to house hack, generate rental income, or expand your investment portfolio. Schedule your showing today!

7322 S Langley Avenue, Chicago

$130,000

4 Beds ⋅ 2 Baths ⋅ 12767603 MLS ⋅ NEW Status

4 BR/2 bath SFH. Full unfinished basement. Two car detached garage.

7343 S Prairie Avenue, Chicago

$310,000

6 Beds ⋅ 4 Baths ⋅ 12774257 MLS ⋅ NEW Status

Welcome to 7844 S Greenwood Ave, Chicago, IL, a spacious 2-flat for sale in Greater Grand Crossing offering an excellent opportunity for real estate investors, owner-occupants, house hackers, and buyers searching for a Chicago multi-family property with rental income potential. This South Side Chicago 2-flat features two spacious 3-bedroom units, each offering nearly 1,000 square feet of living space with bright, sun-filled living rooms, attractive flooring, functional layouts, and in-unit laundry, making the property appealing for tenants, extended families, or buyers looking to live in one unit while generating rental income from the other. Recent improvements add additional value, including a partially repaired roof in 2026, a new rear deck installed in 2026, a replaced gate in 2026, and a basement furnace that is approximately one year old. The property also features a private backyard, two dedicated exterior parking spaces, ample free street parking, and an unfinished basement with separate exterior access that provides valuable storage space and potential future value-add opportunities, subject to applicable Chicago zoning, building codes, and permitting requirements. Located in Greater Grand Crossing on Chicago's South Side, 7844 S Greenwood Ave offers convenient access to the 79th Street/Chatham Metra Electric Station, CTA bus routes, I-90, and the Chicago Skyway, providing easy access throughout Chicago and surrounding areas. Nearby destinations include Grand Crossing Park, the South Shore Cultural Center, the University of Chicago, shopping, restaurants, medical facilities, schools, and everyday neighborhood amenities. Whether you're searching for a Chicago 2-flat for sale, Greater Grand Crossing multi-family home, Chicago investment property, income-producing property, house hacking opportunity, rental property, or South Side Chicago real estate investment, 7844 S Greenwood Ave offers a strong combination of space, rental income potential, recent improvements, parking, commuter access, and long-term value-add potential. Schedule your private showing today and discover the possibilities at 7844 S Greenwood Ave in Greater Grand Crossing, Chicago.

7844 S Greenwood Avenue, Chicago

$299,900

3 Beds ⋅ 3 Baths ⋅ 12773573 MLS ⋅ ACTIVE Status

BACK ON THE MARKET- Brand new roof & freshly staged! Beautifully renovated 4-bedroom (3 +1), 2.1 baths single-family home offering a massive amount of living space across multiple levels. The bright, modern interior showcases new luxury vinyl plank floors and is anchored by a sleek kitchen featuring contemporary cabinetry, quartz countertops, and stainless steel appliances. Upstairs, you'll find three exceptionally spacious bedrooms. Downstairs, the expansive, fully finished basement provides even more room to entertain, featuring a large family room, full bath, and a fourth bedroom or private home office. Throughout the home, the bathrooms have been completely updated with elegant tile and modern fixtures to create a spa-like feel. Complete with a brand-new central A/C system, a detached 2-car garage, and a prime location near shopping, parks, and tollways, this move-in-ready home truly has it all.

7000 S Eberhart Avenue, Chicago

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