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4440 W 55Th Street, Chicago
$655,000
8 Beds ⋅ 6 Baths ⋅ 12668586 MLS
JUMBO TWO FLAT BUILT IN 1986 ON STEPS FROM MIDWAY AIRPORT ! ENTERING THE UNITS YOU WILL VALUE THE EXTRA SQUARE FEET EACH UNITS OFFERS WITH 3 LARGE BEDROOMS AND 1 FULL BATHROOM AND ONE 1/2 BATHROOM PER UNIT PLUS A FORMAL DININGROOM,LARGE KITCHEN WITH PLENTY OF CABINET SPACE WITH REFRIGERATOR AND STOVE INCLUDED PER UNIT .GARDEN UNIT WITH TWO BATHROOMS AND TWO ROOMS.LARGE TWO CAR GARAGE WITH A EXTENDED SHADE " NOT BEING RENTED OUT" SOLD AS-IS CONDITIONS.ROOF ON BUILDING AND GARAGE TEAR OFF 2023.OVER HEAD SEWER WITH SUMP PUMP.WINDOWS ARE SOUND PROOF FROM AIRPORT PROGRAM.IDEAL TO LIVE IN,TRADITIONAL RENT OR SHORT TERM RENTALS. PER SELLERS REQUEST CONVENTIONAL LOAN OR CASH TRANSACTIONS ONLY PREAPPROVAL PRIOR TO VIEWING.

4440 W 55Th Street, Chicago

4437 W 55Th Street, Chicago
$605,000
8 Beds ⋅ 5 Baths ⋅ 12578128 MLS
Multiple offers received. Highest & best due Monday March 9th @ 12:00pm. Solid brick 3 FLAT in prime Chicago location near shopping, dining, parks, schools, METRA and Midway airport. Incredibly spacious units include two 3 bedroom/1.5 bath units and one 2 bedroom/1 bath unit. Large laundry room with coin operated washer and dryer for additional income. Mechanical room with updated heating boiler system. Roof - approximately 8 years old. Windows all replaced within last 10 years. Great backyard space. Detached garage for additional income. Well maintained by long term owner. Ample street parking. Perfect investment opportunity for the savvy investor and owner occupant. Available for immediate occupancy for a live in owner. Lot size 28 x 125 - IMPORTANT - PLEASE DO NOT DISTURB TENANTS.

4437 W 55Th Street, Chicago

5244 S Tripp Avenue, Chicago
$580,000
6 Beds ⋅ 3 Baths ⋅ 12730174 MLS
FULLY REMODELED TWO-UNIT BRICK BUILDING WITH A COMPLETELY FINISHED BASEMENT, FEATURING CUSTOM DESIGNED KITCHENS WITH WHITE SHAKER CABINETS, QUARTZ COUNTERTOPS, MATTE BLACK FINISHES, AND ALL STAINLESS-STEEL APPLIANCES. LUXURY CUSTOM BUILT BATHROOMS, BEAUTIFUL HARDWOOD FLOORS, AND ALL NEW THERMOPANE WINDOWS THROUGHOUT. BRAND NEW HVAC (FURNACES & AIR CONDITIONING), ARCHITECTURAL ROOFS ON BOTH THE HOUSE AND GARAGE, NEW HOT WATER TANKS, NEW GARAGE OVERHEAD DOOR WITH OPENER & TRANSMITTERS, PLUS ALL NEW INTERIOR AND EXTERIOR DOORS AND UPDATED ELECTRICAL PANELS. THE FULLY FINISHED BASEMENT INCLUDES WATERPROOF LUXURY VINYL PLANK FLOORING, A SPACIOUS FAMILY ROOM, ONE BEDROOM, A MODERN BATHROOM, AND A LAUNDRY ROOM. PROPERTY FEATURES OVERHEAD SEWERS, SUMP PUMP, AND A NEW 6' CEDAR PRIVACY FENCE WITH SECURITY GATES. WALKING DISTANCE TO THE CTA ORANGE LINE FOR EASY ACCESS TO DOWNTOWN, CLOSE TO I55, ARCHER AVENUE, PULASKI ROAD, AND MULTIPLE PUBLIC TRANSPORTATION OPTIONS. NEARBY INTERNATIONAL BACCALAUREATE (IB) CURIE HIGH SCHOOL.

5244 S Tripp Avenue, Chicago

5432 S Kilbourn Avenue, Chicago
$575,000
8 Beds ⋅ 3 Baths ⋅ 12639811 MLS
Great investment opportunity! Legal 2-flat with additional garden unit, fully occupied with leases in place. Property features long-term tenants, providing stable and consistent rental income. Ideal for investors seeking a turnkey, income-producing asset. The building is in excellent condition and has been well maintained. It features a newer roof (under 8 years old) and all newer soundproof windows. There are three newer central A/C units and 2 newer furnaces. All units are in great shape, with the third-floor unit offering a newer kitchen and new ceramic flooring. The property also includes a spacious backyard, a two-car garage, and a fully fenced yard. Additionally, the building has been recently tuck-pointed, adding to its overall durability and appeal.

5432 S Kilbourn Avenue, Chicago

5532 S Kilbourn Avenue, Chicago
$505,000
5 Beds ⋅ 3 Baths ⋅ 12462974 MLS
Completely remodeled and updated property with stainless steel appliances, new cabinets and countertops, new Brazilian Cherry hardwood floors all around, new glass handrails, new bathrooms, etc. Everything is new including the entire electrical system, new copper water lines everywhere, new gas lines, etc. Must see property that can easily be rented or used for AirBNB because it is within walking distance to Midway Airport and in a desired location. This property has two separate rental floors plus a full basement that can be used to rent for storage for tenants or can be made into a third unit to rent legally because it has two exits and the celing heights are good. Basement has toilet already installed and has rough-in plumbing for bathroom, kitchen, and even for a laundry room. Great property all-around.

5532 S Kilbourn Avenue, Chicago

5834 S Keeler Avenue, Chicago
$475,000
6 Beds ⋅ 4 Baths ⋅ 12629267 MLS
Turnkey investment opportunity that truly delivers-this multi-unit property is a proven cash-flow powerhouse with the potential to generate up to four separate rental incomes with ease. Whether you're a seasoned investor or looking to build a reliable income stream, this property checks every box for strong ROI and long-term wealth building. Each unit offers comfortable living spaces ideal for tenants, making it easy to maintain consistent occupancy and maximize returns. The flexible layout provides multiple income streams under one roof - live in one unit while the others cover your mortgage, or lease all units for maximum cash flow. It also presents a unique opportunity for a large or extended family setup, offering ample space and privacy while keeping loved ones close under one property. Perfectly positioned just minutes from Midway Airport, this property benefits from unbeatable convenience and accessibility. Tenants will love the proximity to major transportation options, making commuting a breeze. Surrounded by neighborhood parks, popular restaurants, and abundant shopping, the location adds even more value and appeal. Whether you're expanding your portfolio or planning for the future, this is more than just a property-it's a retirement fund that keeps on giving.

5834 S Keeler Avenue, Chicago

5749 S Kenneth Avenue, Chicago
$425,000
3 Beds ⋅ 2 Baths ⋅ 12462775 MLS
Charming and spacious, this beautifully remodeled 4-bedroom, 2-bath home is a must-see. With over 2,100 square feet of comfortable living space, it perfectly blends a cozy exterior with a bright, open interior. Step inside to a sun-drenched dining room, ideal for family gatherings. The heart of the home is a completely renovated kitchen, featuring white shaker-style cabinets, quartz countertops, all-new stainless steel appliances, and abundant storage. The showstopper is the expansive 15x22 great room. Natural light pours in from every angle, highlighting a charming brick accent wall with a wood-burning fireplace. Large windows provide stunning views of the beautifully maintained backyard. The main floor includes two spacious bedrooms, a full updated bathroom with a stand-up shower, and a large pantry. Upstairs, the private primary suite awaits, complete with two large closets. The fully finished basement offers additional living space, featuring a family room, a soundproof home office, a utility and laundry room, and a fourth bedroom and full bathroom. The basement is equipped with an overhead sewer and sump pump, offering peace of mind from any flood concerns. Outside, the 1.5-car brick garage has been completely updated with new doors, a window, and a new roof. This home is in move-in condition and perfectly located just minutes from Midway Airport, major highways, restaurants, and shopping. It's also a short walk to the CTA Orange Line and other public transportation.

5749 S Kenneth Avenue, Chicago

3622 W 54Th Street, Chicago
$420,000
3 Beds ⋅ 2 Baths ⋅ 12740006 MLS
Well-maintained corner-lot home offering space, convenience, and features that are hard to find. Situated on a double lot, this property offers an expansive yard, added privacy, and two separate 2-car garages with parking for up to four vehicles-perfect for extra storage, hobbies, or workspace. Inside, enjoy hardwood flooring throughout the main living areas and a spacious finished lower level with tile flooring and recessed lighting, ideal for a family room, recreation space, home office, or additional living area. Commuters will love the convenient location near CTA bus routes, including the #55 Garfield, with access to the Orange Line, plus easy connections throughout the city. Convenient access to major Southwest Side roadways makes getting around Chicago and the surrounding suburbs a breeze. Double lot, corner location, flexible living space, and an incredible 4-car garage setup-this is a rare opportunity you don't want to miss. Schedule your private showing today!

3622 W 54Th Street, Chicago

5309 S Lawndale Avenue, Chicago
$419,000
3 Beds ⋅ 3 Baths ⋅ 12630484 MLS
Welcome to this well-maintained brick Cape Cod located in the West Elsdon neighborhood. This property features 5 bedrooms and 3 full bathrooms, along with a spacious living room, dining room, and updated kitchen with newer cabinetry and stainless steel appliances. Recent improvements include thermal panel windows, updated bathrooms, refinished hardwood floors, and a newly installed roof. The full finished basement offers additional living space with in-law living arrangement, 2 bedrooms and a full bath. Exterior features include a new fenced yard on both sides, newly added pavers in the backyard, and a 2-car garage with an additional rear-facing garage door, ideal for outdoor gatherings and entertaining. New roof was installed 2025. Additional amenities include central air. Conveniently located near schools, public transportation including the Orange Line, and other neighborhood amenities.

5309 S Lawndale Avenue, Chicago

5339 S Kildare Avenue, Chicago
$405,000
4 Beds ⋅ 3 Baths ⋅ 12414957 MLS
Beautiful & tastefully updated 6-Bed/3-Bth home in Chicago! There's truly nothing left to do but move-in. From the moment you enter the front door, you're greeted by a spacious and bright living room with new paint, hardwood floors and lots of natural light pouring in. The updated kitchen is a stunner with modern porcelain tile flooring, white shaker cabinets, SS appliances and a beautiful backsplash. There are 3 bedrooms and an updated full bath on the first floor as well. Upstairs, you'll find your Private primary suite. The finished basement provides even MORE living space with a family room, the 5th & 6th bedrooms and the laundry area. Outside, enjoy your private, fenced-in backyard - the perfect place to relax on these beautiful summer days! You can't beat this home or it's location - minutes to Midway, major highways, public transit, groceries, restaurants and more! The new garage was built in 2017. New kitchen and new windows in 2020. New roof was done in 2022. Schedule your tour today!

5339 S Kildare Avenue, Chicago

5313 S Tripp Avenue, Chicago
$402,000
3 Beds ⋅ 2 Baths ⋅ 12478367 MLS
Great opportunity to own a Brick 2-unit w finished basement with additional living space / Rooms & additional bathroom. Priced to sell Excellent location nearby Midway Airport. New Bathroom in First floor unit. finished basement could be duplexed with the First-floor unit for a large family or just for more space or work area. Extra wide lot with side driveway for additional parking spaces and easy access to 2 car garage. Basketball hoop on concrete slab in back of property for entertainment and it could be used for additional parking space next to garage & in back of building. Second floor unit for extra income. Listing Office has zoning certificate on file. Easy access to 55 to head to Midway Airport, south suburbs or downtown area. Nice size rooms on second floor unit. New 2nd floor kitchen counter.

5313 S Tripp Avenue, Chicago

5536 S Pulaski Road, Chicago
$400,000
12431292 MLS
Incredible opportunity to own a mixed-use building on high-traffic Pulaski Rd in West Elsdon, with over 30,000 vehicles passing daily. The first floor features approximately 750 sq ft of commercial space currently operating as a barber shop, complete with large storefront windows, a customer restroom, and central heating and air conditioning. The second floor offers a spacious 2-bedroom residential unit with a large kitchen, separate dining room, vinyl windows, and boiler/baseboard heat. Additional highlights include 100 AMP electric service with separate meters, a 2-car garage plus a 3rd vehicle port, and a large rear storage shed currently used by the business. Perfect for an owner-occupant looking to live upstairs and operate a business below, or for an investor seeking strong rental income in a prime location.

5536 S Pulaski Road, Chicago

5413 S Springfield Avenue, Chicago
$399,000
3 Beds ⋅ 2 Baths ⋅ 12533255 MLS
This is the one! Welcome home to your Luxuriously Remodeled beauty featuring 5 bedrooms plus 2 full bathrooms. This captivating property boasts an exemplary mingling of classic sophistication and modern comfort, with diligent mindfulness to detail visible throughout. As you stroll along from above to below you will notice that every area is bathed in beautiful sunshine. You'll be mesmerized by the gleaming hardwood floors and eclectic wood designs of the walls on the 1st floor as you glide to the amazing kitchen that features 42" custom white shaker cabinets, Brazilian quartz countertops, a farm sink, SS appliances, a new roof plus windows, and on and on. With this move in ready home you shall truly enjoy stress free living for the many golden years that lie ahead. Super low property taxes. Perfectly located within walking distance of the Orange Line train station making your commute downtown easy. Enjoy convenient access to I-55, nearby parks, schools, tons of shopping, restaurants, and nightlife. Schedule a showing today and get ready to be wowed. :)

5413 S Springfield Avenue, Chicago

5336 S Harding Avenue, Chicago
$385,000
5 Beds ⋅ 2 Baths ⋅ 12448561 MLS
Wonderful move in ready opportunity with fabulous floorplan. New roof, new windows throughout, recently tuckpointed, updated cooper plumbing in most of the house, updated electrical, 2 new kitchens, new designer bathroom, updated flooring, new wood stairs. Forced air heat and central air conditioning. Sump pump. Open kitchen with new cabinets and beautiful custom stone. Floorplan allows for separate oversized living room and dining room, large bedrooms with great closet space. Oversized lot allows for brick 2 car garage with storage and extra room to spare, patio yard with pavers perfect for entertaining. West exposure yard with amazing afternoon light. Great location with walking distance to the Orange Line, easy walking access to grocery stores, restaurants, coffee shops, stores and more; rare walkable location in highly residential tree-lined neighborhood.

5336 S Harding Avenue, Chicago

5445 S Karlov Avenue, Chicago
$375,000
3 Beds ⋅ 1 Baths ⋅ 12599497 MLS
Beautiful light-filled home, thoughtfully rehabbed in 2023 and perfectly suited for your next chapter. All bedrooms are conveniently located on the main level and feature hardwood floors throughout. The kitchen offers space for an eat-in table, while the spacious living room and skylights throughout the home create a warm and airy feel. Recent updates include a new air conditioner and water heater, both installed in 2024. The home also includes a washer and dryer along with all stainless steel appliances. The finished basement offers high ceilings and an expansive bar area, making it perfect for entertaining, with plenty of additional space for storage, a home office, gym, or recreation. The backyard is ideal for summer gatherings and offers ample space for outdoor furniture and a grill, complete with a privacy fence for added enjoyment. Conveniently located just minutes from Midway Airport, restaurants, shopping, and CTA access. Property taxes does not have an exemption.

5445 S Karlov Avenue, Chicago

3605 W 56Th Place, Chicago
$371,500
3 Beds ⋅ 2 Baths ⋅ 12537013 MLS
Beautifully updated 5 bedroom, 2 bath home offering a thoughtful layout and high end finishes throughout. The upper level features three spacious bedrooms, while two additional bedrooms are located on the lower level. Full bathrooms on both floors provide convenience, with the upper bath offering a relaxing soaking tub and the showers finished with distinctive pebble stone details. Natural light fills the home, highlighting the tall ceilings, modern light fixtures, and wide, open floor plan. Decorative wall trim and paneling add character throughout the main living areas and extend into the lower level. Hardwood flooring flows into the kitchen, which showcases quartz countertops, stainless steel appliances, and a generous eat in layout with a breakfast bar that opens to the dining space ideal for entertaining. Notable upgrades include a granite wet bar, new windows, a new roof, and a new air conditioning system to be connected at closing. The property also features a new 2.5 car garage door with two openers, brand new concrete sidewalks, and a low-maintenance backyard. The finished lower level offers excellent potential for additional living or recreational space. Soft gray wall tones create a clean, modern feel that complements any decor. Conveniently located near shopping, restaurants, schools, and places of worship, this home delivers space, style, and everyday convenience the entire household will appreciate. AS/IS

3605 W 56Th Place, Chicago

5343 S Kostner Avenue, Chicago
$369,900
2 Beds ⋅ 2 Baths ⋅ 12698570 MLS
Welcome to this beautifully maintained 3 bedroom, 2 bathroom raised ranch! Located on a tree-lined street, this move-in-ready home offers the perfect blend of modern updates and functional living space. Step inside to a sun-filled living room featuring hardwood floors and an open, inviting layout. The updated eat-in kitchen is the heart of the home, showcasing stylish shaker cabinetry, stone countertops, stainless steel appliances, and ample space for dining. The main level includes two spacious bedrooms with hardwood flooring and generous closet space, along with a beautifully updated full bathroom. The finished lower level expands your living options with an oversized family room ideal for entertaining, relaxing, or creating a home office space. A third bedroom and second full bathroom provide added flexibility for guests, extended family, or related living arrangements. Outside, enjoy a private backyard perfect for summer gatherings and a detached 2-car garage offering convenience and additional storage. Dry basement! City replaced sewer pipes and owner installed flood prevention system in 2023. Other updates include, but no limited to: new front railing (2024); EV charging system (2024); Custom wood Pergola (2024); Sump pump with Battery backup (2024); Fence around perimeter of house (2025). Conveniently located near schools, parks, shopping, dining, public transportation, and major expressways. 20 minute drive to downtown; 10 minute walk to Pulaski Orange line stop; 1 minute walk to Strokacker Park! Don't miss this exceptional opportunity, schedule your private showing today!

5343 S Kostner Avenue, Chicago

5748 S Kenneth Avenue, Chicago
$360,000
3 Beds ⋅ 2 Baths ⋅ 12669848 MLS
Back on the market! Previous buyer was unable to obtain financing, making this wonderful opportunity available again. No fault of the seller or property. Well-maintained 3 bed, 2 bath home, a bright living room that flows into a spacious eat-in kitchen. Enjoy a vintage style bathroom with personality and timeless flair you won't find just anywhere. The finished lower level offers flexible space with a full bath-ideal for hosting or your own hangout retreat. Move-in ready with room to update at your own pace and build instant equity. A fully fenced backyard, newer concrete sidewalk, and 1-car garage add convenience and outdoor enjoyment. A great option for first-time buyers or owner-occupants looking to invest in their future. Schedule your showing today before this second chance is gone!

5748 S Kenneth Avenue, Chicago

5556 S Tripp Avenue, Chicago
$360,000
3 Beds ⋅ 2 Baths ⋅ 12522857 MLS
One-of-a-kind opportunity to own this solid all-brick ranch, lovingly maintained by its original owner. Offering over 1,800 sq. ft. on the main floor, this spacious home features 3 bedrooms and 2 full baths, along with a bright, flowing layout filled with natural light. Enjoy hardwood floors throughout-some beautifully exposed, others preserved under carpet. The main level includes a formal living room, formal dining room, and a large family room, providing plenty of space for gathering and everyday living. A new radiant heat furnace adds value and peace of mind. The full, unfinished basement is a blank canvas ready for your ideas-perfect for creating additional living space, a recreation area, or storage. While the home offers tremendous potential and does need updating, its size, structure, and location make it an exceptional find. Situated on a desirable corner double lot, the property also features a huge, oversized brick garage for additional storage, work space, or extra vehicles. A truly special home with endless possibilities-don't miss this rare Midway-area gem! To be sold in "AS IS " Condition.

5556 S Tripp Avenue, Chicago

3633 W 58Th Place, Chicago
$359,900
3 Beds ⋅ 2 Baths ⋅ 12594677 MLS
Welcome to 3633 W 58th Place, a beautifully maintained home that reflects true pride of ownership. Featuring a spacious living room filled with natural light and gleaming hardwood floors throughout. The bright eat-in kitchen offers granite countertops, maple cabinets, and stainless steel appliances, perfect for everyday living. The fully finished, updated basement provides additional living space with a 4th bedroom and second full bathroom. UPDATES: fresh paint (2026), roof (2022), furnace (2024), and basement flooring (2026). Enjoy a spacious backyard ideal for relaxing or entertaining. Conveniently located near restaurants, shopping, Midway Airport (7 min.), and major highways (10 min.), offering easy access to all that Chicago has to offer.

3633 W 58Th Place, Chicago

3927 W 56Th Street, Chicago
$357,000
6 Beds ⋅ 3 Baths ⋅ 12415460 MLS
Welcome to this well-maintained 2-flat in the highly convenient West Elsdon neighborhood! Each unit features 3 spacious bedrooms, with the first floor offering a formal dining room-perfect for gatherings and everyday living. The second-floor unit includes central air conditioning for year-round comfort. The property also boasts a partially finished basement, ideal for additional living space or storage. Enjoy peace of mind with several recent updates: newer thermal pane windows, a 4-year-old roof on both the home and garage, and siding that was replaced just 3 years ago. A 2-car garage provides secure off-street parking. This move-in-ready home is just a short walk to the Orange Line and conveniently located near Midway Airport, shopping, schools, and more. Whether you're looking to live in one unit and rent the other, or add a solid investment to your portfolio, this property checks all the boxes!

3927 W 56Th Street, Chicago



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