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$659,000
4 Beds ⋅ 3 Baths ⋅ 12762156 MLS ⋅ ACTIVE Status
Rare opportunity to own a well-maintained legal 2-flat situated on an oversized 43' x 125' lot in the Jefferson Park/Portage Park area. The property features two spacious units, each with 2 bedrooms and 1 full bath, offering flexibility for owner-occupancy, extended family, or investment. A full basement provides additional finished space, including a full bathroom, an additional room, and a kitchenette area. Numerous improvements include newer windows and doors, updated kitchens, and a newer 2.5-car detached garage. The oversized lot provides excellent outdoor space and is a standout feature for the area. Conveniently located near transportation, shopping, restaurants, parks, and neighborhood amenities.

5849 W Wilson Avenue, Chicago

$269,900
12 Beds ⋅ 4 Baths ⋅ 12758567 MLS ⋅ ACTIVE Status
GREAT INVESTMENT OPPORTUNITY -This rare 12bedroom, 4bath, 4,908 sq ft quadruplex built in 1900 offers exceptional income potential with 3 units currently vacant and 1 units rented monthtomonth. Whether you're expanding your portfolio or seeking a highyield valueadd property, this one stands out from the rest. Units are functional but would benefit from light "updating" during turnover and some fresh paint (one unit needs minimal drywall work)- Recent Updates / Systems & Exterior: heating units have systems approximately 10 years old, Cooling: No central air; window units used for cooling and back porches (all four porches) rebuilt ~12 years ago-AsIs Sale- Investment Highlights Estimated ARV around $440,000 based on area comps- Strong rental upside with 12 bedrooms across four units- 3 units ready for immediate renovation and leasing (1 unit is leased until 10/27), Unique charm and historic character not found in other local quadruplexes. This property offers tremendous potential for investors seeking cashflow, valueadd opportunities, or longterm appreciation. This won't last - don't miss out on a onceinalifetime opportunity! Cash buyers, Hard money buyers, Conventional financing buyers.

7321 S Stewart Avenue, Chicago

$589,000
6 Beds ⋅ 3 Baths ⋅ 12761961 MLS ⋅ ACTIVE Status
Great opportunity to own a legal 3-unit corner building situated between Chicago's Hermosa and Humboldt Park neighborhoods. Each unit features 2 bedrooms plus a den, providing additional flexible space for an office, sitting area, or other use. The property features separate gas and electric meters for each unit, along with individual central air conditioning and furnaces that are approximately 3 years old. The roof is approximately 6 years old. The ground-floor unit is only a few steps below grade and offers good ceiling height, with laundry hookups conveniently located nearby. Parking is a major plus with a 2-car garage, additional carport, and permit street parking. With three legal units, separate utilities, newer mechanicals, flexible layouts, and multiple parking options, this property is well suited for an investor or owner-occupant. Sold As-Is.

1755 N Kedvale Avenue, Chicago

$1,099,000
9 Beds ⋅ 6 Baths ⋅ 12762032 MLS ⋅ ACTIVE Status
Magazine Caliber Simply Stunning, Massive Expansive footprint, with 3 car garage New Construction 3 flat all 3 bedroom 2 baths set on over sized 152 deep lot. Exceptional, Elegant, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Full Back splash, Fireplace with Custom Mill Work and indirect Lighting, Mud Rooms, Wide Plank Engineered Flooring, Accent Wall Cohesive Design offering relief from ordinary, sequestered primary suite, lifestyles primary bathroom offer Opulent over sized Shower w/ Frame less Glass, & Custom Mirrors and designer plumbing fixtures. Professional closet organizers throughout, 3 car Garage. Urban Intimacy w/ Hyper Convenience Experience excellence. Veteran developers of 25 + years, 1 year warranty included. Hyper Convenient, AAA Trophy Piece Perfect Turn key, Owner Occupied, Investor or 1031.This is exceptional property and location. IMMEDIATE Delivery. Pictures are from actual project. Actual* Monthly Income $8950/ $105,000 Annual/7.5 CAP Move in ready Ask about preferred lender incentives *Unit 3 at value

4841 S Prairie Avenue, Chicago

$1,549,000
7 Beds ⋅ 7 Baths ⋅ 12762020 MLS ⋅ ACTIVE Status
Newer Construction Passive Home 3 Unit building right on Harrison Park- Full Masonry Perfect Wall, All Electric energy-efficient and intelligently engineered for optimal living conditions. Three Bedroom/2.1 Bath Duplex, 2nd floor 2 bed/2 bath & Penthouse 2 bed/2 bath with interior stair to penthouse room and full finished rooftop deck. Excellent views of Harrison Park, the City and abundant natural light. Hardwood floors, Modern Kitchens designed for entertaining with Gray shaker cabinets with quartz countertops, island, full backsplash, and stainless-steel appliances. All bedrooms generously sized to accommodate king sized beds and the bathrooms are finished in Carrera porcelains and brushed nickel. Thoughtful storage and walk-in closets throughout. Rear deck system and washer/dryer in each unit. 3 car Outdoor secured parking. Amazing location, very short walk to the Pink Line and 18th Street with all its vibrancy; Thalia Hall, Canton Regio, Brew Brew PLUS Harrison Park with tennis courts, full gym, indoor swimming pool soccer pitch and all Pilsen has to offer! Builder built for himself and spared no expense- top floor will be vacant at close, perfect for owner-occupant! Grss Annual Income $124,740. NOI $96,555. 6.2 Cap Rate

1815 W 19Th Street, Chicago

$1,225,000
9 Beds ⋅ 6 Baths ⋅ 12762019 MLS ⋅ ACTIVE Status
Welcome to the Calumet Collection, Magical Storybook Street Setting, Magazine Caliber, Simply Spectacular. Expansive footprint New Construction 3 flat all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Floor to Ceiling Windows, Professional Fully Appointed Slim Line Sleek Kitchen Cabinetry, Under Cabinet Lighting, Integrated Stainless Steel Appliances, Quartz Island Full Back Splash & Waterfall Edge. Custom Mill Work, Wet and Dry Bars, Premium Wide Plank White Oak Hardwood Floors, Acoustic Panel Feature Wall with Media Console, Cohesive Design offering relief from ordinary, sequestered primary suite, lifestyles primary bathroom offer Opulent oversized Shower w/ Frameless Glass, Double Vanity, Custom Mirrors & Niches paired with designer plumbing fixtures. Professional closet organizers throughout. Unit 3 features interior Floating Staircase to Loft Bonus room with Wet Bar and Cantilevered Roof Deck equipped with gas, water, power completed in composite with option to expand offers Sensational City Views plus Additional Front Glass Terraces, rear patio and 3 Car Covered Carport Urban Intimacy w/ Hyper Convenience Experience excellence. Hands on Veteran developer includes 1 year builder warranty. Hyper Convenient, AAA Trophy Piece Perfect Turnkey, Owner Occupied, Investor or 1031. This is part of a 3 building series. This is exceptional property and location. IMMEDIATE Delivery. Pictures are from actual project. Projected Monthly $9650/ $115,800 Annual/ 7.8 CAP Ask about preferred lender incentives

4130 S Calumet Avenue, Chicago

$339,900
2 Beds ⋅ 2 Baths ⋅ 12761535 MLS ⋅ ACTIVE Status
Cool, affordable, and move-in ready, this exceptional two-flat offers a rare opportunity for both owner-occupants and investors alike. Both units are in excellent condition and ready for immediate occupancy, whether you're looking to live in one unit and generate rental income from the other or add a turnkey property to your portfolio. Ideally located just blocks from the 550-acre Jackson Park, featuring lakefront access, a golf course, harbor, and the Obama Presidential Center campus, this property also offers a short walk to Metra service for an easy commute. Each unit features 2 spacious bedrooms and 1 full bath, providing comfortable, efficient living with strong rental appeal. With its desirable location, move-in-ready condition, and attractive price point, this is an outstanding value you won't want to miss.

6820 S Dante Avenue, Chicago

$299,900
8 Beds ⋅ 4 Baths ⋅ 12761976 MLS ⋅ ACTIVE Status
STRONG POSITIVE CASH FLOW IN THE HEART OF BACK OF THE YARDS Welcome to 4504 S Paulina St, a solid and well-maintained legal 3-unit building offering an excellent investment opportunity with positive cash flow. The property features three separate apartment units: First Floor Front Unit: Spacious apartment First Floor Rear Unit: Separate apartment Second Floor: Full-floor unit extending from front to rear All three units are legally configured as a 3-unit property. An additional benefit for investors is that tenants pay their own gas and electric, helping keep operating expenses lower and supporting strong cash flow. This is an excellent opportunity for an investor or owner occupant looking for a cash-flowing multifamily property in Back of the Yards, with multiple rental units and tenant-paid utilities. Property Highlights: Legal 3-unit building 2 units on the first floor 1 full-unit apartment on the second floor Positive cash flow Tenants pay gas and electric Strong investment opportunity Located in Back of the Yards

4504 S Paulina Street, Chicago

$149,999
5 Beds ⋅ 3 Baths ⋅ 12761944 MLS ⋅ ACTIVE Status
***** CASH OR RENOVATIONS LOANS ONLY ***** Approved Legal 3 unit!! Building consists of a total of 5 bedrooms and 3 bathrooms. On the first floor unit you will find an open concept kitchen/living room area along with 2 bedrooms, huge pantry, and 1 full bath.On the second level unit, you find another 2 bedrooms, 1 bath, with a full kitchen and living room. Downstairs in the ground unit you will find 1 huge bedroom, 1 full bath annd open layout kitchen/ living room Combined. Each unit has its own high efficiency furnace along with their own individual entrance and exits. There is an ample front yard, private balcony, and gated throughout! Located in highly incoming New city! Potential to earn 4K plus in monthly cash flow! LOW TAXES! PROPERTY WAS REHABBED IN 2022 WITH NEW KITCHENS, BATHROOMS, CENTRAL AIR SYSTEMS. Schedule your showing today! ***** CASH OR REHAB LOANS ONLY AS THERE ARE SOME CITY VIOLATIONS THAT WILL NEED TO GET ADRESSED*****

4329 S Wood Street, Chicago

$900,000
4 Beds ⋅ 4 Baths ⋅ 12761589 MLS ⋅ ACTIVE Status
2418 N Western Avenue is a well-configured four-unit property located in the heart of Bucktown. The property features three units in the front building plus a detached coach house in the rear, offering four separate 1-bedroom/1-bathroom units. Each unit is separately equipped with its own HVAC system, hot water tank, and electric panel. The property also features common-area laundry located in the basement of the rear coach house, along with one exterior parking space accessible from the alley. Rents are currently below market, providing meaningful upside for a new owner. The four units currently generate an average rent of $1,756 per month compared to an estimated market average of $2,300 per month. Unit 2F is currently in the process of moving out, creating an opportunity for an owner-occupant or investor seeking flexibility. Ideally situated at the convergence of Bucktown, Logan Square, and West Lakeview, 2418 N Western Avenue offers convenient access to the Western Blue Line station, expressway, and multiple bus routes. The property combines strong neighborhood connectivity with immediate rental upside and a flexible four-unit configuration.

2418 N Western Avenue, Chicago

$785,000
8 Beds ⋅ 4 Baths ⋅ 12752374 MLS ⋅ ACTIVE Status
Classic brick 3-unit in the highly sought-after Heart of Chicago neighborhood of Pilsen, offering an exceptional opportunity for investors or owner-occupants. The property features two 2 bedroom, 1 bath apartments on the first floor, front and rear units, plus an expansive 5-bedroom, 2-bath top-floor residence with outstanding potential. The top-floor unit offers interior access to a large unfinished attic, creating an exciting opportunity to duplex up and add additional living space, value, and rental income. Both the top-floor apartment and rear first-floor unit are currently occupied. The unfinished basement offers even more potential, with roughed-in plumbing for a bathroom, rear egress, and a common laundry area. Situated in one of Pilsen's most vibrant areas. Surrounded by restaurants, cafes, and neighborhood favorites. Enjoy convenient access to the Pink Line and short drive to expressways.

2420 S Oakley Avenue, Chicago

$689,900
7 Beds ⋅ 3 Baths ⋅ 12737561 MLS ⋅ ACTIVE Status
Legal 3-Unit Investment & Owner-Occupant Opportunity! This well-maintained legal 3-unit property offers the opportunity to live in one unit while generating rental income from the other two. The building features new windows, oversized gutters, copper plumbing, and new garage door. The first and second-floor units offer individual central heat and air, while the garden unit features radiant floor heat. Interior highlights include hardwood floors, oak cabinets, and granite countertops. Additional features include a 2-car garage and owned coin-operated washer and dryer. Tenants pay their own gas and electric. Conveniently located near public transportation, restaurants, shopping, and schools. A solid opportunity for an investor or owner-occupant looking to add a 3-unit property to their portfolio.

2327 N 75Th Avenue, Elmwood Park

$275,000
6 Beds ⋅ 2 Baths ⋅ 12761752 MLS ⋅ ACTIVE Status
BACK ON MARKET, NO FAULT OF SELLER! Previous buyer's financing fell through after they were unable to obtain their anticipated grant. Don't miss another opportunity to own this spacious brick 2-flat in Chicago's Chatham community. Offering 6 bedrooms and 2 full bathrooms, each unit features 3 bedrooms and 1 bath, making this a great option for an owner-occupant or investor. The finished basement provides additional flexible living and recreational space.The property has received numerous improvements in 2026, including a newly resealed roof (July 2026), fresh interior paint (July 2026), new bathroom sinks in both units (July 2026), front, side and rear tuckpointing, chimney tuckpointing and repairs, newly stained and sealed second-floor hardwood floors (March 2026), repaired and reinforced hallway stairs, water heater repairs with new hardware, plumbing repairs including resolution of basement leaks, and drywall repairs with fresh paint.Rear parking provides space for 2 vehicles. Conveniently located near public transportation, neighborhood schools, shopping and everyday amenities. The 79th Street Chatham Metra Electric station is nearby, providing rail service toward downtown Chicago, while neighborhood grocery options include ALDI. Schedule your showing today and take another look at everything this property has to offer!

7948 S Drexel Avenue, Chicago

$439,900
5 Beds ⋅ 2 Baths ⋅ 12754063 MLS ⋅ ACTIVE Status
Prime McKinley Park location overlooking the park. This clean, well-maintained, all-brick 2-flat offers an excellent opportunity for an owner-occupant, multigenerational household or investor seeking a solid property in one of McKinley Park's most desirable and convenient locations. The first-floor apartment features 2 bedrooms and 1 bath, while the second-floor apartment offers 3 bedrooms and 1 bath. Both apartments feature comfortable layouts and eat-in kitchens. The second-floor unit has been nicely updated with stainless steel appliances, forced-air furnace and central air conditioning. A full unfinished basement provides abundant storage and utility space. Outside, the property continues to deliver. A fenced rear yard provides valuable private green space for gardening, pets, outdoor entertaining or future landscaping enhancements. A concrete walkway leads to the all-brick detached 2-car garage with alley access, providing highly desirable off-street parking and additional storage potential. The location is truly the standout feature. Directly across from McKinley Park-an approximately 69-acre "oasis in the city"-residents can enjoy expansive green space, recreation and neighborhood amenities right outside their door. The property is also just one block from Archer Avenue and the Orange Line station, providing convenient access to public transportation, shopping, dining and downtown Chicago. A rare opportunity to own a well-maintained brick 2-flat with a 2-car garage in a prime park-facing location. Whether you're looking to live in one unit while generating rental income from the other or add a solid asset to your investment portfolio, this property offers an outstanding combination of location, flexibility and long-term potential. Building is in excellent condition and will be conveyed As-Is. Buyer pre-approval and disclosures to accompany offers.

2204 W 37Th Street, Chicago

$439,900
4 Beds ⋅ 3 Baths ⋅ 12759351 MLS ⋅ ACTIVE Status
Take a look at this beautiful two-unit building in Berwyn! This well-maintained property features original beautiful hardwood floors and an amazing staircase welcoming you through the main entrance. Each floor offers 2 bedrooms, 1 bathroom, a spacious living room, and a kitchen. The main bedroom in each unit includes a bonus room that can be used as a walk-in closet, office, nursery, or additional living space. The property also features a 2-car garage and a full basement with laundry, additional rooms that can be used for storage, an office, or extra living space, plus a full bathroom. The flat roof has 4 inches of silicone insulation, providing added insulation and energy efficiency. All windows have been replaced with insulated windows. The building is in excellent condition and has had numerous upgrades completed over the past few years. A great opportunity for an owner-occupant or investor looking for a solid two-unit property in Berwyn. Call your local Realtor today to schedule your private tour before it's too late! 'SOLD AS IS'

1240 S Maple Avenue, Berwyn

$550,000
6 Beds ⋅ 2 Baths ⋅ 12753893 MLS ⋅ ACTIVE Status
Great opportunity to own 2-unit property located in Chicago's Portage Park neighborhood minutes from Jefferson Park and Mayfair. Both units are currently occupied with leases in place through May 2027. Tenants pay electric and gas. Interiors feature vintage character, including woodwork and built-in hutches, with spacious kitchens and formal dining rooms. The property also includes enclosed back porch, unfinished basement with storage and laundry space, unfinished attic, and a detached two-car garage. Conveniently located less than a mile from two CTA Blue Line stations and the Jefferson Park Metra station, with easy access to I-90 and Milwaukee Avenue, shopping, dining, parks, and other neighborhood amenities.

5102 W Sunnyside Avenue, Chicago

$429,900
7 Beds ⋅ 5 Baths ⋅ 12761477 MLS ⋅ ACTIVE Status
Exceptional investment opportunity! Legal 4-unit building with an additional non-conforming owner suite unit, potentially offering 5 total income streams. Ideal for investors or owner-occupants seeking strong cash flow with value-added potential. This property has so much potential for overall income and cap rate. Property features a full unfinished basement, brick 4-car garage, and a concrete car pad secured by a wrought iron gate for additional parking or storage. Two adjacent lots included in the sale. The fenced in lots features an open green space-perfect for outdoor enjoyment today with long-term potential for development, expansion, or additional income opportunities. Ideally located just minutes from the Illinois Quantum and Microelectronics Park, positioning the property for long-term growth and increased demand. Sold as-is.

9655 S Commercial Avenue, Chicago

$799,000
9 Beds ⋅ 5 Baths ⋅ 12760344 MLS ⋅ ACTIVE Status
Welcome to this 4-unit investment opportunity in prime Bridgeport! Oversized corner property with approximately 3,818 sq ft, 9 bedrooms, 5 bathrooms, 4 legal units plus a bonus unit. Flexible unit mix includes 1 three-bedroom, 2 two-bedroom, and 2 one-bedroom layouts - ideal for investors or owner-occupants looking to house-hack. Features include 10'+ ceilings, open-concept kitchens, private porches, 6 gas meters, 6 electric meters, and coin-operated laundry provides an additional source of income. Expansive unfinished basement, newer tear-off roof (about 5-6 years new), newer porch, some newer windows, and detached 2-car garage. Rents are currently below market, offering potential upside. Projected annual income of approximately $88,800. Conveniently located near I-55, Archer Ave, CTA Bus #62, Orange Line, Palmisano Park, Morgan and Halsted dining/entertainment, Cermak Produce, Mariano's, Chinatown, Downtown, Guaranteed Rate Field, lakefront, and more. Excellent opportunity to add a multi-unit property to your Bridgeport portfolio!

3001 S Haynes Court, Chicago

$310,000
6 Beds ⋅ 4 Baths ⋅ 12759130 MLS ⋅ PRICE CHANGE Status
Discover the potential of 7844 S Greenwood Ave, a spacious Chicago 2-flat in the Greater Grand Crossing area offering an ideal opportunity for owner-occupants, house hackers, and real estate investors looking for rental income, long-term appreciation, and value-add potential. Each unit offers 3 bedrooms and nearly 1,000 square feet of living space with bright, sun-filled living rooms, attractive flooring, and the convenience of in-unit laundry, creating a functional layout for both tenants and multi-generational living. Recent improvements add even more value, including a partially repaired roof in 2026, a rear deck replaced in 2026, replaced in 2026, and a basement furnace that is approximately one year old. Additional features include a private backyard, two dedicated exterior parking spaces, ample free street parking, and an unfinished basement with separate exterior access that provides useful storage and future value-add potential, subject to applicable zoning and permitting requirements. Commuters will appreciate the convenient location near the 79th St./Chatham Metra Electric station, CTA bus routes, I-90, and the Chicago Skyway, while nearby destinations such as Grand Crossing Park, the South Shore Cultural Center, the University of Chicago, local shopping, dining, and everyday neighborhood amenities add to the property's appeal. Whether you're searching for a Chicago 2-flat for sale, a Greater Grand Crossing multi-family home, an income-producing property, a house hacking opportunity, or a South Side Chicago investment property, 7844 S Greenwood Ave delivers a compelling combination of space, location, recent updates, rental potential, and future upside. Schedule your private showing today and explore everything this well-positioned Chicago multi-unit property has to offer.

7844 S Greenwood Avenue, Chicago

$399,900
7 Beds ⋅ 3 Baths ⋅ 12759489 MLS ⋅ ACTIVE Status
So much potential and so close to the finish line! This substantially renovated two-unit property offers a great opportunity for an owner-occupant or investor willing to complete the remaining finishing touches. Much of the heavy lifting has already been done, with extensive improvements completed in 2026, including updated electrical, plumbing, modern kitchens and baths, flooring and additional interior improvements. Offering approximately 2,058 square feet of building area, 7 bedrooms and 3 bathrooms in total, the property features a 2-bedroom, 1-bathroom first-floor unit and a spacious 5-bedroom, 2-bathroom duplex-up. Both units are currently vacant, providing flexibility for an owner-occupant or investor without existing tenants or leases. Priced to reflect the property's current condition and remaining punch list items, this is an opportunity to step into a property where much of the renovation work has already been completed and finish it to your own vision. A two-car carport provides off-street parking, with potential space for a future garage subject to City approval. The City of Chicago zoning certificate reflects two dwelling units. Property is being sold strictly AS-IS. Seller will not make repairs or provide repair credits. Buyer is responsible for independently verifying the property's condition, square footage, improvements, permits, zoning and intended or future use.

5320 S Laflin Street, Chicago

$489,900
5 Beds ⋅ 2 Baths ⋅ 12760717 MLS ⋅ ACTIVE Status
Beautifully updated brick two-unit building located in the highly desirable Brighton Park neighborhood! This well-maintained property is an excellent opportunity for both investors and owner-occupants. The first-floor unit features 2 bedrooms, 1 full bath, a spacious living room, dining room, and an updated kitchen with attractive cabinetry, quartz countertops, a pantry, and new appliances. The second-floor unit offers 3 bedrooms, 1 full bath, a bright living room, dining room, and new appliances. Both units include an enclosed rear porch, providing additional usable space. The property also features an unfinished basement with endless potential for storage, laundry or future finishing, plus a detached 2-car garage. Conveniently located near schools, parks, shopping, restaurants, and public transportation with easy access to major highways. Property is being sold AS IS.

4589 S Archer Avenue, Chicago

$959,900
9 Beds ⋅ 6 Baths ⋅ 12760624 MLS ⋅ ACTIVE Status
Gorgeous NEW Construction Oversized 3-unit in prime Washington Park Location, Set alongside another New Development by the same developer and with rent and sales comps already established. Modern design with the perfect blend of city living and convenience. Each unit has a spacious, open-concept layout and condo-quality features, such as 42" cabinets, stainless steel appliances, recessed lighting, in-unit laundry. Each unit is a large 1,500 sq ft, 3 bed/ 2 bath, with a luxury master bathroom at the rear and extra built-out storage closets. The units will rent easily and proforma rents are $8,400/month. The top unit features a vaulted ceiling and decorative railings for an added touch of luxury. Unit has cameras built in for security, plus the ButterflyRX system for entry, which is a cloud-based video intercom system that allows residents to manage building access, grant entry to visitors, and receive deliveries directly from their smartphones. This property offers unbeatable convenience, 2 minute walk to CTA line and easy access to Washington Park. Prime investment opportunity, positioned for cash flow, appreciation, and creating generational wealth in one of Chicago's most exciting neighborhoods. Can arrange property management for any out-of-state buyers.

5167 S Michigan Avenue, Chicago



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