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$254,900
2 Beds ⋅ 2 Baths ⋅ 12707579 MLS ⋅ NEW Status
Remodeled 4 bedroom 2 bathroom brick bungalow with PLENTY to offer in Chatham! Situated on a corner lot, this home features a living room and dining room with an electric fireplace in the living room, a remodeled kitchen with white cabinets, granite countertops and stainless steel appliances, remodeled bathrooms and a new 2-car garage! The primary bedroom has a huge walk-in closet. The loft style finished basement includes the 3rd and 4th bedrooms, a laundry room and storage. This home won't last long. Move in before the end of the Summer! Within a short distance to the expressway, shopping, schools, parks and public transportation.

8301 S Maryland Avenue, Chicago
$59,900
2 Beds ⋅ 1 Baths ⋅ 12713203 MLS ⋅ ACTIVE Status ⋅ Chatham Court Condos BLDG.
Attention smart buyers and investors!!!!!! Welcome to your new urban sanctuary or your immediate cash flow investment! Unbeatable value on Chicago's South Side! This ready-to-go 2-bedroom condo in Chatham is perfect for a first-time homebuyer or savvy investor. Featuring a smart layout, this unit is located in a highly efficient, low-upkeep building that makes living easy. Incredible location just minutes from the CTA Red Line, Metra, I-94, Chatham Plaza shopping, and local dining favorites. Why rent when you can own for less? Easy to show-book your private viewing today!

8136 S Drexel Avenue Unit #2, Chicago
$600,000
12711631 MLS ⋅ ACTIVE Status
Rare chance to acquire a fully vacant 17-unit building in Chicago's Chatham neighborhood at $600K, roughly $35K/unit. Property requires a complete gut rehab, giving an investor total control over unit mix, finishes, and systems from day one. Location is a major draw: steps to Cottage Grove Ave, minutes to the Dan Ryan Expressway for fast downtown access, and close to Metra and CTA Red Line service for tenants commuting citywide. The 79th Street retail corridor and neighborhood staples like Dat Donut and Harold's Chicken Shack are nearby, along with Avalon Park and Hamilton Park for green space. Chicago State University sits just a few minutes away, adding to steady rental demand in the area. Chatham remains one of the South Side's most stable multifamily submarkets, with strong owner-occupant pride and consistent rental demand. This is a ground-up repositioning play for an investor looking to build a fully renovated, high-cash-flow asset from scratch. Bring your contractor and your vision, this one's ready to be rebuilt from the studs up.

7954 S Maryland Avenue, Chicago
$149,000
4 Beds ⋅ 2 Baths ⋅ 12711472 MLS ⋅ PRICE CHANGE Status
This solid all-brick two-flat is a rare find-perfect for savvy investors or owner-occupants seeking rental income! Each spacious unit features 2 bedrooms and 1 bath, complemented by newer windows that enhance energy efficiency and curb appeal. The property includes a detached 2-car garage and a full basement offering additional storage or expansion potential.

8036 S Dobson Avenue, Chicago
$79,000
2 Beds ⋅ 1 Baths ⋅ 12707229 MLS ⋅ ACTIVE Status
*** Multiple Offers Received Highest and Best Due 7/28 5pm*** Welcome to 7930 S Maryland Ave, a classic Chicago brick bungalow offering an incredible value-add opportunity for savvy investors and rehabbers alike. This solid-bones property features 2 comfortable bedrooms and 1 bathroom, providing a fantastic foundation to build immediate equity. You can skip the headache of major structural overhauls, as the roof, windows, hardwood flooring, plumbing, electrical, and mechanicals are all in place and functional. Even better, the HVAC system and ductwork are already installed, saving you significant time and expense on your renovation. The real magic lies in the massive expansion potential. This home is primed for customization, offering a blank canvas to drastically increase your square footage by adding extra bedrooms and a bathroom in the full basement with high ceilings, or by dormering the spacious attic. Outside, you will find a nice backyard perfect for summer gatherings and a convenient detached garage. Opportunities with this much fundamental work already completed do not last long in this market. Bring your design ideas and unlock this property's true potential today!Sold as-is.

7930 S Maryland Avenue, Chicago
$99,900
3 Beds ⋅ 2 Baths ⋅ 12710745 MLS ⋅ ACTIVE Status
Great Investment or Homeownership Opportunity! All brick two-story townhouse featuring 3 bedrooms, 1.5 bathrooms, full basement, and large, fenced yard. Conveniently located just north of the 87th Street corridor in East Chatham, this spacious corner unit offers easy access to schools, shopping, dining, services, transportation, and more. Inside, the open living and dining area combine original hardwood flooring with bright natural light from east and south facing windows. A recently updated kitchen provides a western exposure, along with access to a private covered deck and massive fenced yard, perfect for outdoor entertaining or--for added value--potential parking. Upstairs, a welcome retreat showcases a generously sized main bedroom, two secondary bedrooms, and a bathroom with full amenities. Additional features include a half bathroom on the main level plus a full unfinished basement with laundry on the lower level, an ideal location for future expansion or current storage needs. No HOA fees. Repairs and updates needed. Sold AS IS.

8610 S Ingleside Avenue, Chicago
$419,000
9 Beds ⋅ 6 Baths ⋅ 12706520 MLS ⋅ ACTIVE Status
Excellent investment opportunity! This well-maintained, three-unit building was constructed in 2007. Each unit offers 3 bedrooms and 2 full bathrooms with a master suite. Units 1 and 2 are currently occupied by month-to-month tenants, Unit 3 is vacant features stainless steel appliances, including a stove, refrigerator, dishwasher, and microwave, to be installed before closing. Each tenant pays their own gas and electric,. The owner pays for water and trash. The roof and exterior are maintained annually. A great opportunity for an investor or owner-occupant!

7918 S Greenwood Avenue, Chicago
$1,100,000
12703883 MLS ⋅ ACTIVE Status
7914 S Dobson Avenue is a 13-unit vintage brick walk-up in Chicago's Chatham submarket. Heavy 1BR mix (101BR + 32BR) in a 9,700 SF castle-style brick property - battlement parapets, corner turret, and Gothic-arch entry built to 1928 masonry standards.

7914 S Dobson Avenue, Chicago
$315,000
4 Beds ⋅ 2 Baths ⋅ 12703065 MLS ⋅ ACTIVE Status
Welcome to this beautifully updated 6-bedroom, 2-bath bungalow offering the perfect blend of space, comfort, and value! This move-in-ready home features generous room sizes, an updated interior, and a brand-new roof for added peace of mind. The versatile floor plan provides ample space for large or multi-generational households, a home office, or guest accommodations. Conveniently located near parks, schools, shopping, dining, and major expressways, this property offers both comfort and accessibility. Don't miss this incredible opportunity to own a spacious, updated home that's ready for its next owner. Schedule your private showing today!

8305 S Maryland Avenue, Chicago
$300,000
4 Beds ⋅ 2 Baths ⋅ 12697427 MLS ⋅ ACTIVE Status
Welcome to 8419 S. Maryland Ave., a spacious 4-bedroom, 2-bathroom home offering comfort, functionality, and plenty of room to grow. Thoughtfully designed with generous living spaces and a versatile floor plan, this home is ideal for everyday living, entertaining, or accommodating a larger household. Inside, you'll find bright, inviting rooms, well-sized bedrooms, and two full bathrooms that provide convenience for family and guests alike. The flexible layout offers endless possibilities to personalize the space and make it your own. Outside, enjoy a private backyard perfect for relaxing, gardening, or hosting summer gatherings. Conveniently located near schools, parks, shopping, dining, and public transportation, this home combines neighborhood charm with easy access to city amenities.

8419 S Maryland Avenue, Chicago
$108,000
2 Beds ⋅ 1 Baths ⋅ 12679569 MLS ⋅ ACTIVE Status
Don't miss this nice two (2) bedroom townhome in this spacious, quiet area of Chatham. Freshly painted, rehabbed bath room, and laminated floors. Priced just right, and perfect for first time home buyers. Thanks in advanced for touring.

7931 S Dobson Avenue Unit #A, Chicago
$115,000
2 Beds ⋅ 2 Baths ⋅ 12668322 MLS ⋅ ACTIVE Status
Affordable beautifully rehabbed 2 bedrooms, 1 and half bathrooms Townhouse. The kitchen has brand new cabinets and granite countertops with stainless steel appliances. Microwave, washer and dryer are also included. Motivated seller is willing to assist buyer with closing costs.

7939 S Ingleside Avenue Unit #C, Chicago
$445,300
10 Beds ⋅ 5 Baths ⋅ 12664564 MLS ⋅ ACTIVE Status
***SHOWINGS START 6/15/2026*** Attention investors and owner-occupants - exceptional 4-unit brick building in rapidly appreciating Chatham near the lakefront and Obama Presidential Center. Property features two spacious 4-bedroom units (1 4bd/2ba and 1 4bd/1ba) with full living and dining rooms, plus two 1-bedroom units offering strong rental diversification. All units include updated kitchens and baths, modern plank flooring, stainless steel appliances, and abundant natural light. Recent exterior upgrades include new privacy fence, backyard patio ideal for grilling and entertaining, and 2-car brick garage with remote access. On-site laundry room plus maintenance/storage lounge. Strong rental demand with appreciation and rent growth potential. Ideal for FHA, owner-occupant, or long-term investor hold. SOLD AS IS.

8017 S Maryland Avenue, Chicago
$119,000
2 Beds ⋅ 1 Baths ⋅ 12644701 MLS ⋅ ACTIVE Status
Stunning 1st-floor 2 bed/1 bath condo offering everything today's buyers are looking for! Features include a modern updated kitchen, beautiful hardwood flooring, and a bright, inviting layout throughout. 1 parking space is included in the price. Move-in ready and impeccably maintained - this is a must-see unit!

950 E 86Th Street Unit #105, Chicago
$300,000
12597834 MLS ⋅ ACTIVE Status
Owner retired - motivated sale! Excellent investment or owner-user opportunity in Chicago's desirable Chatham business district. This one-story greystone and brick commercial property features six retail storefronts with strong visibility and 100 feet of frontage along busy Cottage Grove Avenue. The property is currently income-producing with four established tenants in place. Two stores are vacant. Tenants are responsible for all utilities except water. The rear of the property provides ample parking with 12+ spaces, a valuable amenity for both tenants and customers. There are 4 separate pin numbers. With some TLC and the right management from a savvy business owner, this property has the potential to generate substantial income. Sold "as is" condition. The building needs new roof!

8237 - 8245 S Cottage Grove Avenue, Chicago
$207,000
4 Beds ⋅ 2 Baths ⋅ 12545155 MLS ⋅ ACTIVE Status

7926 S Drexel Avenue Unit #1, Chicago
$595,000
12572665 MLS ⋅ ACTIVE Status
Exceptional investment opportunity! This well-maintained 6 unit multi-family property offers a total of 10 bedrooms and 6 bathrooms, making it ideal for both long term and short term rental strategies. Each unit features its own kitchen, living room, and dining area, offering comfortable, fully independent living spaces for tenants or guests. The property is equipped with a 24 hour security surveillance system for added peace of mind. Exterior amenities include six dedicated parking spaces for residents and guests. Two units are currently leased, providing immediate, stable income. Three units are operating as active Airbnb rentals, with one unit already secured for 160 rental days. One additional unfinished unit needing rennovations presents an opportunity for updates and added value.

8624 S Maryland Avenue, Chicago
$219,999
12575484 MLS ⋅ ACTIVE Status

8115 S Cottage Grove Avenue, Chicago



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