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Browse All Chicago IL 5 Bedroom Properties for Sale

$90,000
5 Beds ⋅ 2 Baths ⋅ 12682418 MLS ⋅ CONTINGENT Status
Attention Investors and Rehabbers! This solid 2-unit in Englewood offers significant potential for investors or buyers looking to renovate and add value. Each unit provides great potential for rental income or make it your own. Live in one and rent out the other. Located in a residential neighborhood with access to local amenities, schools, and public transportation, this property is ideal for those seeking a hands-on investment with long-term upside. Buyer to verify zoning and take subject to municipal requirements. Sold As Is. Seller does not provide survey. Utilities will not be activated. *Property not for rent - beware of rental scams.*

5556 S Princeton Avenue, Chicago
$537,000
5 Beds ⋅ 3 Baths ⋅ 12677954 MLS ⋅ ACTIVE Status
Welcome to 4935 W Henderson Street, a solid brick 2-flat located in the highly desirable Portage Park Neighborhood. This property offers spacious units featuring original hardwood floors, generous living and dining rooms, separate utilities, and central heating and air conditioning. Each unit provides flexible living space with multiple bedrooms, making it ideal for owner-occupants, investors, or multi-generational living. Broker is related to the seller

4935 W Henderson Street, Chicago
$2,200,000
5 Beds ⋅ 4 Baths ⋅ 12678506 MLS ⋅ CONTINGENT Status
Elegant 5 Bedroom Lincoln Park home with classic finishes and a comfortable, thoughtful, floor plan. The first floor features spacious living and dining areas centered around a handsome marble-clad, gas-started, wood-burning fireplace. The inviting chef's kitchen offers always desirable white cabinets, accented by Quartzite counters and island top with a dove gray cast, complemented by a similar backsplash. The room overflows with storage and still has room for a table with easy seating for six. Step down into a warm, comfortable family room featuring the second of three wood-burning fireplaces and attractive built-ins. Light oak floors and staircases with trestle carpeting are featured, with carpeted bedrooms throughout. On the second floor, three bedrooms and two baths are featured. The Primary is a sun filled, private space, complete with a fireplace, large spa styled bath, offering a Whirlpool tub, separate shower, and double bowl sink. In addition, a spacious laundry room features a full sized Whirlpool washer and dryer. The third level is a very adaptable space that currently is used as a combination office/ gym and leads to a large private deck with Trex decking. The lower level offers two bedrooms and a bath plus a fun family space for tv bingeing or a game of pool. Not to be outdone, the rear of the home features a private patio, generous two car garage with an EV charger and very large private deck with Trex floor covering. The location could not be more appealing. Tree lined street, vibrant DePaul University as a neighbor, Oscar Mayer school district, and a two-block walk to the" L". A great place to call home!

1032 W Montana Street, Chicago
$145,000
5 Beds ⋅ 1 Baths ⋅ 12679802 MLS ⋅ PRICE CHANGE Status
HUGE FIVE BEDROOM HOME WITH UNFINISHED BASEMENT WAITING FOR YOUR POSSIBILITIES. TWO CAR GARAGE PLUS TWO ADDITIONAL PARKING SPACES. OVERSIZED LOT WITH SPACIOUS BACK YARD ON A DEAD-END QUIET BLOCK. REAL HARDWOOD FLOORS. ROOF IS A COUPLE YEARS OLD. TENANT OCCUPIED AND WILL REMAIN OCCUPIED AT CLOSING.

327 E 136Th Place, Chicago
$200,000
5 Beds ⋅ 3 Baths ⋅ 12679099 MLS ⋅ ACTIVE Status
Investor opportunity in the heart of Roseland! This spacious 2-story property offers over 2,700 square feet of living space across three levels and is packed with income-producing potential. Featuring 5 bedrooms, 3 full bathrooms, and a kitchen on each level, the flexible floor plan is well suited for a variety of investment strategies, including multigenerational living, shared housing, or a value-add renovation. The main level offers spacious formal living and dining rooms with gleaming hardwood floors, generously sized bedrooms, and a functional layout. The expansive basement provides additional living and entertaining space, further increasing the property's versatility. Outside, the large backyard with a concrete patio and newer 2-car detached garage adds to the home's appeal. With only cosmetic updates needed, this property presents an excellent opportunity to add value and maximize returns. Whether you're looking to renovate and resell, expand your rental portfolio, or create a high-demand living arrangement, the possibilities are endless. Property is being sold as-is. FHA 203(k) financing welcomed. Don't miss this exceptional value-add opportunity in an established neighborhood with strong upside potential.

10224 S Princeton Avenue, Chicago
$390,000
5 Beds ⋅ 3 Baths ⋅ 12678169 MLS ⋅ PENDING Status
Welcome to this spacious and well-maintained brick bungalow in the heart of Gage Park! Offering three levels of living space, this impressive home features 7 bedrooms and 3 full bathrooms, providing plenty of room for a variety of living arrangements. The main level showcases beautiful hardwood floors, a bright living room, formal dining room, and generously sized bedrooms. The finished upper level and finished basement add valuable living space, including additional bedrooms, a full bath, family room, and a second kitchen. Additional features include thermal-pane windows, central air conditioning, an enclosed porch, a 2-car garage, and an extra parking apron. Conveniently located near schools, shopping, dining, parks, and public transportation. This move-in-ready home offers exceptional space, functionality, and value. Schedule your showing today!

5741 S Sawyer Avenue, Chicago
$549,000
5 Beds ⋅ 3 Baths ⋅ 12673539 MLS ⋅ CONTINGENT Status
Excellent Bridgeport investment opportunity. This solid brick three-unit building includes two rental units plus a spacious three-bedroom owner's unit, offering strong flexibility for an owner-occupant or investor. The property also features a basement and a two-car garage, adding valuable storage, parking, and utility space. Located in a desirable Bridgeport area close to neighborhood amenities, transportation, and local development, this property is a must-see for buyers looking for income potential and long-term value.

1339 W 31St Street, Chicago
$689,900
5 Beds ⋅ 4 Baths ⋅ 12677666 MLS ⋅ CONTINGENT Status
Introducing Deux on Evans, where qualified buyers automatically receive a $20,000 grant that may be applied toward eligible closing costs and qualifying funds needed to purchase the home. Qualified buyers may also be eligible for up to $70,000 through the City of Chicago's grant programs. Together, these grants create one of the most compelling opportunities to own a new construction home in Chicago. Welcome to Deux on Evans, a striking new construction two-unit residence where contemporary design, sophisticated living, and long-term opportunity converge in the heart of West Woodlawn. Bold modern architecture, expansive windows, and thoughtfully curated finishes immediately distinguish this exceptional property. Inside, soaring ceilings, wide-plank flooring, oversized windows, and an open-concept design create bright, inviting spaces that are equally suited for everyday living and effortless entertaining. The designer kitchen serves as the heart of the home, featuring rich wood-toned cabinetry, quartz countertops, dramatic pendant lighting, premium appliances, and an oversized island that naturally brings family and friends together. Sophisticated finishes and clean architectural lines continue throughout, creating a timeless aesthetic that blends modern luxury with everyday comfort. What truly sets Deux on Evans apart is the beautifully appointed garden residence, offering exceptional flexibility and income-producing potential. Whether utilized as a long-term rental, furnished executive residence, corporate housing, or a short-term rental where permitted by applicable laws and regulations, the additional residence creates an outstanding opportunity to generate supplemental income while building long-term wealth. Its location makes it especially appealing to visiting professors, physicians, researchers, graduate students, medical professionals, and families visiting the University of Chicago, as well as guests traveling to experience the highly anticipated Obama Presidential Center, Jackson Park, and Chicago's vibrant South Side. It also serves as an ideal home away from home for executives, consultants, traveling medical professionals, and others working in Chicago on temporary assignments who appreciate the comfort, privacy, and space that a luxury residence offers over a traditional hotel. Perfectly positioned near the University of Chicago, the Obama Presidential Center, Jackson Park, the South Shore lakefront, the Museum of Science and Industry, golf courses, neighborhood restaurants, parks, and convenient transportation, this home is located in one of Chicago's most exciting and rapidly evolving communities, where continued investment is shaping the future. Deux on Evans offers something increasingly rare: a luxury residence that elevates your everyday lifestyle while creating meaningful financial opportunity. Whether you're searching for an exceptional place to call home, a residence with built-in income potential, or both, this extraordinary property delivers an unmatched combination of contemporary design, flexibility, and lasting value. Luxury without compromise. Opportunity without limits. Welcome to Deux on Evans.

6637 S Evans Avenue, Chicago
$659,000
5 Beds ⋅ 4 Baths ⋅ 12673209 MLS ⋅ ACTIVE Status
Attainable, comfortable, healthy, and cool! Award-winning, Greenline Homes Two Flat in Southeast Woodlawn! Greenline Homes has made Woodlawn the destination for high-performance homes in Chicago. We're thrilled to offer a resale of a groundbreaking two-unit building that showcases cutting-edge construction and high-performance materials and design throughout. Unit 1 is a bright, modern garden unit with two bedrooms. Unit 2 is a spacious and modern 3-bedroom/2.5-bath duplex. Sustainable without compromise. Both units boast beautiful and durable quartz countertops, custom cabinetry, and energy-efficient appliances. Own your energy. The building includes a solar photovoltaic system on the roof, which produces much of the building's energy needs and reduces the building's carbon footprint with clean, free renewable energy. Efficiency by design. Engineer-designed and sized zoned Mitsubishi heating and cooling provide extreme comfort and efficiency to both units. Comfort is built right in. Incredible engineered insulation, triple-pane glass, and an air-sealed building envelope make this building quieter and more comfortable than any standard building on the market. Healthy air is standard. Energy return ventilators and Panasonic whisper-quiet exhaust fans ensure consistent, high-quality indoor air while maintaining peak efficiency. The low-maintenance lifestyle. Well-designed exteriors with high-quality materials like James Hardie siding and commercial-grade roofing reduce maintenance, allowing your home to work harder for you, instead of you working hard for it. Greenline Homes is making sustainable, green homes more accessible, and now you can own a sustainable green home with income! Plus, a 2-car garage is included. The home is currently leased, and access for showing is limited. Located steps to Metra Electric Trains, Jackson Park, and the Obama Presidential Center.

1221 E Marquette Road, Chicago
$495,000
5 Beds ⋅ 2 Baths ⋅ 12675937 MLS ⋅ CONTINGENT Status

1627 N Washtenaw Avenue, Chicago
$725,000
5 Beds ⋅ 3 Baths ⋅ 12672666 MLS ⋅ ACTIVE Status
This well-kept craftsman home in Jackson Park Highlands is set on a 50 x 134 sf lot; what appears to be small and quaint from the outside is deceptively large at just under 4,700 sf. One large cozy room reveals itself to another with natural light that follows you throughout the day. This home features 5 bedrooms, 3 bathrooms, wrap-around terrace, expansive recreation room, and a two-car garage. Upon entering, the foyer opens up to a large hallway with views into the dining room and living room that is large enough to have multiple seating areas. French doors allow access to the terrace from the living room and adjacent family room making this home comfortable for indoor/outdoor entertaining. In the kitchen, stainless steel appliances and granite countertops make food prep and cooking easy. Walk through the dining room to a private area at the rear of the house where the primary suite is located with its own screened porch. Just past the second bedroom are stairs to three additional bedrooms and another full bath on the second floor. In the basement, you will find a finished recreation room with a wet bar. An office, full bathroom, laundry/mechanical room and storage areas complete the lower level. Below the generously sized two-car garage is a full basement. Its caddy corner location on the property creates a lovely outdoor space to read a book or have dinner on a summer night with friends. This property is sold AS-IS and will shine with a few creative thoughts and aesthetic ideas. Walk to play a round of golf at the Jackson Park Golf Course or to the lakefront trail; the Obama Presidential Center is only minutes away. Easy access to Metra, CTA, and DuSable Lake Shore Drive will take you directly to the Loop.

6840 S Constance Avenue, Chicago
$250,000
5 Beds ⋅ 5 Baths ⋅ 12673283 MLS ⋅ ACTIVE Status
Investor / Redevelopment Opportunity in Roseland! Rare chance to acquire two separate parcels with income, adaptive reuse, and redevelopment potential. Buyer may explore rezoning to B2-2, with potential for up to 8 units per lot / 16 total units, subject to zoning approval, plans, permits, and buyer verification. Situated on a combined 50 ft x 140 ft site, the property offers flexibility for investors, developers, nonprofits, owner-users, or faith-based organizations. Strong potential for affordable studio apartments in an area where attainable housing remains in demand. Offered at $325,000 with room to negotiate for a qualified buyer. Bring your vision to this value-add opportunity in Chicago's Roseland neighborhood.

127 E 107Th Street, Chicago
$1,349,900
5 Beds ⋅ 4 Baths ⋅ 12672399 MLS ⋅ CONTINGENT Status
*Look! Low interest assumable Loan* This is impeccably designed luxury turnkey 3 unit in the hot Avondale area bordering Logan Square was completely renovated completed in 2019 from the foundation up to the roof sits on an oversized Chicago lot with 3 outdoor parking spaces. All kitchens offer custom cabinetry with under cabinet lighting, granite counter-tops, backsplashes, deep sinks with sprayers, GE stainless steel appliances including dishwashers and microwaves. The large bathrooms offer Kohler soaking tubs and fixtures, spacious vanities, honeycomb and rain inspired tile. The HVAC units, tankless water heaters, in-unit washer/dryers, and wide plank rustic hardwood floors on floors 1 and 2 and herringbone ceramic floor tiles in the Garden Unit were all installed between 2018-19. Each unit is equipped with recessed lights with dimmers throughout. Each level has its own outdoor space which include 3 large outdoor decks and 1 patio. Special features for the 2nd floor duplexed-up unit include a beautiful island with room to maneuver, 2 bathrooms, with 1 major bathroom with a double sink and walk-in shower shower sprayer located off the oversized major bedroom at the top level. A den sits right off the top level deck. Skylights brighten the upper level. The exterior includes newer roof, gutters, siding, custom encasement windows and vinyl double hung windows throughout the building (2018). The foundation was waterproofed, the concrete newly poured, new "I" beams, columns, drain-tile, plastic barrier, sump pump and ejector pit. The structure insulated with spray foam, new electrical system from the service throughout the building. New copper plumbing throughout. New low voltage and cable wiring throughout. Freshly painted wrought iron and wood decks. Garage was built just two years ago. All walking distance to grocery shopping, parks and public transportation. Truly a wonderful location to call home!

2821 N Springfield Avenue, Chicago
$240,000
5 Beds ⋅ 2 Baths ⋅ 12670853 MLS ⋅ ACTIVE Status

5646 S Sangamon Street, Chicago
$359,900
5 Beds ⋅ 2 Baths ⋅ 12672036 MLS ⋅ PENDING Status
Property Highlights: Legal 2-unit multifamily building 5 total bedrooms and 2 bathrooms Approximately 2,238 square feet Detached garage Strong rental income potential for investors or owner-occupants Convenient commuter location Near major employers, hospitals, universities, and transportation hubs

1124 S Sacramento Boulevard, Chicago
$289,800
5 Beds ⋅ 3 Baths ⋅ 12667002 MLS ⋅ CONTINGENT Status
Income-producing Exceptional opportunity to own a well-maintained 2-unit building on a quiet, desirable block. Perfect for investors seeking strong rental income or owner-occupants looking to offset their mortgage with rental revenue. The first unit features 2 bedrooms and 1 bathroom, while the spacious duplex-down unit offers 3 bedrooms, 2 bathrooms, and a second kitchen, providing excellent flexibility for related living, extended family arrangements, or additional living space. This property stands out with a finished duplex-down layout already in place and an unfinished attic offering exciting potential for future expansion, additional bedrooms, office space, or customized living areas (buyer to verify all possibilities). Conveniently located near parks, schools, public transportation, grocery stores, shopping, restaurants, and everyday amenities. Easy access to neighboring communities and major thoroughfares makes commuting a breeze. Whether you're building your investment portfolio or searching for the ideal owner-occupied property, this versatile multi-unit offers space, income potential, and future upside all in one.

5237 S Princeton Avenue, Chicago
$289,000
5 Beds ⋅ 2 Baths ⋅ 12667382 MLS ⋅ CONTINGENT Status
Gorgeous 5 BR 2-Flat home nestled on a Roseland cul-de-sac street, each unit with SS kitchen appliances, hardwood floors, updated bathrooms, fantastic light fixtures, recessed lights, chandeliers and ceiling fans, and bright two-tone paint throughout w/chair rail. The full basement has a W/D and is awaiting your storage, duplex down or ADU vision and creativity. Enclosed back porch leads to the gated exterior which encloses a large backyard, 2-car garage (built 2019), back to front concrete walkway, front porch and yard. Near transportation, Block Park, Gately Park Stadium, local schools, healthcare, shopping, dining, supermarkets, health clubs and other area amenities.

Chicago
$255,000
5 Beds ⋅ 2 Baths ⋅ 12668405 MLS ⋅ CONTINGENT Status
Solid, family-owned brick two-flat that has been maintained for more than 50 years and offers great curb appeal. This charming property features hardwood floors throughout both units, blending timeless vintage character with thoughtful modern updates. Each spacious unit offers generous living areas, including a bright sunroom and living room with a vintage fireplace, providing ample space for large furniture and comfortable everyday living. The first-floor kitchen and bathroom have been completely renovated within the last few years, adding modern convenience while preserving the home's character. The first-floor unit also provides direct access to the basement, presenting a potential opportunity for a duplex-down conversion. Both units feature separate dining rooms, eat-in kitchens, and deep pantry storage, making them ideal for daily living and entertaining. The full unfinished basement spans the entire length of the building and offers endless possibilities for additional living space, storage, or future improvements. Outside, you'll find a nice sized backyard perfect for relaxing or entertaining. Recent improvements include: * Back porch rebuilt in 2018 * 75 Gallon Hot water tank replaced in 2023 * First-floor kitchen renovation (2023) * First-floor bathroom renovation (2021) * Boiler professionally serviced annually This property is being Sold As-Is. Don't miss this rare opportunity to own a maintained, character-filled two-flat with excellent potential and long-term pride of ownership.

5430 S May Street, Chicago
$105,000
5 Beds ⋅ 2 Baths ⋅ 12609762 MLS ⋅ CONTINGENT Status
Investor Special! Don't miss this excellent opportunity to add to your investment portfolio. This detached single-family home offers tremendous potential for investors, rehabbers, or buyers looking to customize a property to their vision. Featuring a spacious layout with a basement, first floor, and second floor, this property provides ample space and endless possibilities. The basement already includes plumbing for an additional bathroom, offering added value and expansion potential. Conveniently located near schools, public transportation, shopping, and major roadways. Property is being sold AS-IS. Bring your ideas and unlock the value of this promising investment opportunity. AS-IS Sale

8106 S Burnham Avenue, Chicago
$540,000
5 Beds ⋅ 3 Baths ⋅ 12573000 MLS ⋅ ACTIVE Status
Come see this beautifully maintained and thoughtfully updated 5-bedroom, 3-full-bath home in sought-after Garfield Ridge. The home is filled with natural light and offers a spacious open-concept layout with numerous recent upgrades throughout. The main level features new flooring (2025), fresh paint, updated lighting, new carpet in the living room, and an updated kitchen with stainless steel appliances, quartz countertops, and a new backsplash. A main-level bedroom and fully renovated full bath are conveniently located just off the kitchen. Upstairs boasts new windows, a new stair railing, and a spacious primary bedroom with an additional lounge area and new ceiling fan. Three additional generously sized bedrooms share a fully remodeled full bathroom. The finished basement offers new flooring (2023), a second full kitchenette, a full bathroom with new laminate flooring, and an additional office space-perfect for extended living or work-from-home needs. Additional highlights include an updated A/C unit, new dryer, and all three bathrooms fully updated. The backyard is ideal for entertaining with a new pool liner and sand filter. Conveniently located near shopping, dining, expressways, and more.

5304 S New England Avenue, Chicago
$799,000
5 Beds ⋅ 3 Baths ⋅ 12665271 MLS ⋅ ACTIVE Status
Ukrainian Village/West Town two flat with in law unit in the basement. Wonderful opportunity and location to redevelop into your dream home! City lovers this is your chance.

1814 W Haddon Avenue, Chicago
$229,900
5 Beds ⋅ 2 Baths ⋅ 12665026 MLS ⋅ ACTIVE Status
Excellent investment opportunity in Chicago's South Shore neighborhood! This spacious brick mixed-use 2-unit building offers incredible upside potential for investors or owner-occupants looking to build long-term wealth. Featuring a desirable unit mix with 5 total bedrooms and 2 full bathrooms, separate utilities, individual furnaces, updated electrical, newer mechanicals including furnace and hot water tank, and a full unfinished basement offering additional storage and future possibilities. Both units feature functional layouts with generous living space, fresh paint, updated finishes, and well-maintained kitchens and baths, including a recently remodeled second-floor bathroom. The second-floor 3-bedroom unit features a spacious private deck with city views, adding additional outdoor living space. The property also includes a fully fenced backyard and 2-car garage, providing valuable off-street parking. Located minutes from Lake Michigan, multiple beaches, golf courses, public transportation, shopping, restaurants, and the future Obama Presidential Center, this location offers strong long-term growth potential. Whether you're looking to house hack, expand your rental portfolio, or secure a potential income-producing property, this solid Chicago brick multi-unit offers the location, features, and upside investors are looking for. Don't miss this South Shore opportunity!

1835 E 79Th Street, Chicago
$260,000
5 Beds ⋅ 2 Baths ⋅ 12664904 MLS ⋅ ACTIVE Status
6-bedroom, 1.5-bath brick home in the South Deering/Trumbull Park area! Features hardwood, ceramic, and laminate flooring, remodeled bathrooms, stainless steel refrigerator and stove, and quartz kitchen countertops. Master bedroom bath. The main level offers 3 bedrooms, with 2 dormer-style bedrooms on the upper level and 1 large bedroom in the basement. Shingle roof, and circuit breakers. Basement includes both interior and exterior access. Garage with awning. Oversized Chicago Lot. Fast access to I-90/I-94. Close to Marian R. Byrnes Natural Area and Trumbull/Lyman Park.

10134 S Bensley Avenue, Chicago
$179,900
5 Beds ⋅ 2 Baths ⋅ 12662871 MLS ⋅ CONTINGENT Status
Excellent opportunity for investors or owner-occupants! This investor-friendly 2-flat duplex offers the perfect chance to live in one unit while generating income from the other, or maximize cash flow by renting both units. The property is ready for your creative vision with minor cosmetic updates and presents immediate income-producing potential. Conveniently located near parks, schools, shopping, transportation, and major commuting routes. Whether you're looking to expand your investment portfolio or achieve house-hacking success, this property checks all the boxes. Bring your ideas and unlock the potential, this one won't last long! **Package Deal** 6715 S Bishop St Chicago IL is also being sold

11317 S Edbrooke Avenue, Chicago
$179,900
5 Beds ⋅ 2 Baths ⋅ 12662897 MLS ⋅ ACTIVE Status
Investor-friendly 2-flat duplex offering a fantastic opportunity to build wealth and generate income from day one! This property features solid bones and is ready for your vision with minor cosmetic updates. Whether you're an experienced investor looking to expand your portfolio or a buyer seeking a value-add opportunity, this property offers tremendous potential. Bring your ideas, add your personal touch, and start collecting rental income immediately. Conveniently located near schools, shopping, public transportation, and major expressways. Opportunities like this don't come around often. Schedule your showing today because this property won't last long! **Package deal** 11317 S Edbrooke Ave Chicago IL is also being sold by seller

6715 S Bishop Street, Chicago
$409,900
5 Beds ⋅ 3 Baths ⋅ 12661649 MLS ⋅ PENDING Status
Exceptional craftsmanship and thoughtful design shine throughout this beautifully renovated 5-bedroom, 3-bath home. Bathed in natural light, the spacious living and formal dining areas offer an inviting setting for gatherings both large and small. The stunning kitchen is the heart of the home, featuring granite countertops, a breakfast bar, glass tile backsplash, stainless steel appliances, and room for a kitchen table. The open-concept floor plan creates seamless flow between the main living spaces. A brand-new second-story addition expands the home with three generously sized bedrooms, including a private primary retreat complete with a luxurious en-suite bath, dual vanities, and an oversized walk-in shower. Two additional bedrooms and a full bath on the 2nd level provide versatility for family, guests, or a home office. Positioned on a desirable corner lot, the property also offers a fenced yard and a spacious 2.5-car garage. Completely transformed from top to bottom, this impressive home delivers the space, quality, and finishes today's buyers are searching for.

9044 S Throop Street, Chicago
$450,000
5 Beds ⋅ 3 Baths ⋅ 12662690 MLS ⋅ CONTINGENT Status
Rare opportunity in the heart of Garfield Ridge. This expansive all-brick Chicago Bungalow delivers over 4,000 sq ft of fully finished, heated living space across three levels, a true standout in the neighborhood. With 6 bedrooms and 3 full baths, the layout is ideal for large families or multi-generational living, featuring a fully independent second floor with its own living room, three bedrooms, and a primary bedroom. The finished basement adds over 1,200 sq ft of additional space complete with a dedicated laundry room and a classic laundry chute from the second floor. Hardwood floors throughout the main floor, with hardwood waiting under the rugs on the second floor as well. Major mechanicals are within 5-10 years of age, including the furnace, boiler, solar panels, and roof for both the home and garage.

5530 S Merrimac Avenue, Chicago
$389,000
5 Beds ⋅ 3 Baths ⋅ 12647844 MLS ⋅ CONTINGENT Status

6811 S Washtenaw Avenue, Chicago
$599,998
5 Beds ⋅ 5 Baths ⋅ 12662032 MLS ⋅ ACTIVE Status
Thoughtfully composed for modern ownership, 1435 S. Trumbull introduces a new-construction two-flat where refined design and income-producing flexibility share one cohesive address. Anticipated for October 2026 delivery, the property pairs a contemporary brick-and-Hardie exterior with two independently functional residences, a two-car garage, rear deck, fenced backyard, and approximately 2,900 square feet of combined living space. The approximately 1,900-square-foot duplex-up unfolds across two well-proportioned levels with three bedrooms and 2.5 baths. An open-concept main floor connects the living, dining, and kitchen areas, while expansive west-facing windows invite warm afternoon light. Wide-plank LVT flooring, five-inch baseboards, crown molding, modern lighting, and crisp black accents establish a polished visual language throughout. At the center of the home, custom black-and-white cabinetry is paired with quartz countertops, a substantial island, and a complete GE stainless steel appliance package. Generous storage and workspace support daily routines and larger gatherings, while the adjoining rear deck extends the living space outdoors. Upstairs, the primary suite offers a quiet, design-forward retreat with a spa-inspired bath. A freestanding soaking tub, glass-enclosed walk-in shower with full-body sprayers, double vanity, wood-look accent wall, and curated Kohler, Delta, and Signature Hardware fixtures create a layered, restorative setting. Two additional bedrooms, a second full bath, and second-level laundry complete the duplex with intention. The approximately 1,000-square-foot garden residence adds two bedrooms, two full baths, 10-foot ceilings, a private entrance, full kitchen, in-unit laundry, and separate utility meters. Its independent configuration creates meaningful versatility for rental income, guests, or other flexible living arrangements without compromising privacy. Set in North Lawndale, the home is near historic Douglass Park, the Garfield Park Conservatory, and La Catedral Cafe, a locally loved destination for Guadalajara-inspired breakfast and coffee. The Kedzie Pink Line station, CTA bus connections, and nearby I-290 provide convenient access to the West Loop, Downtown Chicago, and surrounding neighborhoods. More than a new build, 1435 S. Trumbull is a thoughtful approach to city living-designed to support comfort today while creating possibilities for what comes next. Photos depict the previously completed model at 2435 W. Congress Parkway and are representative of the planned design and finishes at 1435 S. Trumbull. Qualified buyers may be eligible for up to $100,000 in purchase-price assistance through the City of Chicago's Building Neighborhoods and Affordable Homes Program. Income, owner-occupancy, program guidelines, and fund availability apply; buyers should independently verify eligibility with the City of Chicago.

1435 S Trumbull Avenue, Chicago
$1,450,000
5 Beds ⋅ 4 Baths ⋅ 12567829 MLS ⋅ ACTIVE Status
Exceptional opportunity in the highly sought-after Kinzie Park community. This 5-bedroom, 3.1-bath, four-level townhome offers approximately 3,500 square feet of refined living space within one of River North's most exclusive gated enclaves. Located within the 6.5-acre riverfront community of Kinzie Park, this residence offers privacy, security, and a lifestyle rarely found in downtown Chicago. The home features expansive living areas, generous bedroom sizes, and multiple levels designed for both comfortable daily living and effortless entertaining. The top level is ideal for hosting, complete with a wet bar, beverage refrigerator, enclosed den/office (or optional bedroom), and direct access to a private roof deck with city views. The flexible floor plan provides versatility for work-from-home needs, guest accommodations, or additional living space. Kinzie Park is a fully gated community with 24-hour security, beautifully landscaped grounds, brick-paved streets, a private river walk, and complimentary guest parking. Townhome residents enjoy full access to the community's amenities, including a pool and fitness center located within the adjacent high-rise building. Unmatched location between Kinzie & Grand and Clinton & Canal, directly along the Chicago River. Just steps from the Loop, Merchandise Mart, East Bank Club, premier River North and West Loop dining, shopping, public transportation, and major expressways. O'Hare International Airport is approximately 30 minutes away. A rare opportunity to own a spacious, turnkey townhome in one of downtown Chicago's most private and amenity-rich communities.

481 N Clinton Street, Chicago
$3,500,000
5 Beds ⋅ 8 Baths ⋅ 12658546 MLS ⋅ ACTIVE Status
Introducing a truly one-of-a-kind duplex in one of the city's premiere boutique buildings with endless opportunities to create your dream home. Located across from Lakeshore Park and steps from the lakefront, this homes offers spectacular views of the city, park, lake, and Navy Pier. Enjoy over 6800 sq. ft. of expansive living and entertaining spaces along with 3 terraces, five en-suite bedrooms, a study, and a lounge/bar. This incredible space offers versatility for every aspect of your life. There are nearly limitless options to tailor the space to suit your needs along with a strong investment opportunity should one decide to re-create two separate residences. Five parking spaces and 3 large storage areas are included in this price, truly making this a once in a lifetime value.

270 E Pearson Street Unit #701-801, Chicago
$999,999
5 Beds ⋅ 2 Baths ⋅ 12655638 MLS ⋅ CONTINGENT Status
North Center/Lincoln Square! Welles Park/Coonley School/ Queen of Angels School/ Brick 2 Unit with basement and laundry 2yr New 2 Car Garage, 3bdrm 1bth and 2bdrm 1bth units with hardwood floors, Gas forced heat and Central air. Same owners since 1985! Restaurants, Cafes, Old Town School, Davis Theater, Convenient transportation. SOLD "AS IS" Conventional or "CASH OFFERS ONLY " please see additional info

4315 N Oakley Avenue, Chicago
$279,900
5 Beds ⋅ 2 Baths ⋅ 12656848 MLS ⋅ ACTIVE Status
Huge investment opportunity! Solid brick 2-flat built in 1970 featuring a full basement, separate utilities, corner lot, and 2-car garage. Conveniently located near schools, parks, shopping, Metra station, and CTA bus stop. Great potential for investors or rehabbers. Don't miss this opportunity! Property is being sold AS IS. CASH ONLY.

7448 S Maplewood Avenue, Chicago
$169,000
5 Beds ⋅ 2 Baths ⋅ 12656322 MLS ⋅ ACTIVE Status

10941 S Wentworth Avenue, Chicago
$299,000
5 Beds ⋅ 2 Baths ⋅ 12653972 MLS ⋅ CONTINGENT Status
Exceptional opportunity in a solid brick single-family home offering 5 bedrooms and 2 full bathrooms, including a private master suite. Major renovations were initiated in 2019 with key system upgrades already completed: new electrical, new plumbing, new furnace, and a new tankless water heater-providing peace of mind and a strong foundation for future value. This property sits in an area experiencing ongoing revitalization, strong rehabs, and increasing development activity. Surrounded by both renovated homes and new construction, the neighborhood offers excellent long-term upside. With hardwood floors throughout and only minor finishing touches needed, this home is ideal for investors, rehabbers, or end users looking to build equity quickly. A true value-add opportunity in a strategically positioned area-ready for the next owner to maximize its full potential.

1133 N Kedvale Avenue, Chicago
$265,000
5 Beds ⋅ 3 Baths ⋅ 12628910 MLS ⋅ CONTINGENT Status

2736 S Kildare Avenue, Chicago
$1,900,000
5 Beds ⋅ 4 Baths ⋅ 12628802 MLS ⋅ ACTIVE Status
MOVE-IN THIS FALL! NOW UNDER CONSTRUCTION! Introducing RiverWard - a collection of 35 new construction, extra-wide row homes tucked along the north branch of the Chicago River. Perfectly situated in an idyllic location and with access to Southport, Roscoe Village, and the expressway, this exclusive offering will deliver contemporary new construction row homes never before available in the neighborhood. Residence 20-B boasts an idyllic and never-before-available location on the north bank of the Chicago River, delivering over 4700 SF of indoor and outdoor living space plus 335 SF private fenced yard. Designed by acclaimed-developer ZSD in conjunction with Sullivan, Goulette & Wilson, the EXTRA-WIDE (22 FEET!) home boasts sophisticated and functional design for today's homebuyer in a space WIDER than a single-family home. Spanning four levels of living, this 5-bedroom residence delivers a family room, loft office with skyline views, private rooftop, and two car garage parking. All four bedrooms are on the same, upper level with the option to add a 5th bedroom to the first level. At the heart of this home is a spacious, contemporary kitchen, with immense cabinet count and integrated appliances from Sub-Zero, Wolf, and Bosch, designed to cater to both the casual cook and the culinary enthusiast. The massive quartz waterfall peninsula and full-height cabinetry throughout provides the desired function and storage expected from a single-family home. This home includes an open-concept living and dining room and a private 225 SF walkout terrace complete with gas, water, and electric. A separate Powder Room and oversize Family Room finish off the large main level. The impressive, extra-wide Primary Suite is designed as a personal retreat with large bedroom, dressing room, and "wet room" bathroom with European glass shower, standalone tub, skylight, and double vanity with quartz countertop. Traversing to the rooftop unveils a private loft office and 300 SF private rooftop terrace with skyline views. Two side-by-side garage parking spaces ensure you have all the comforts of a single-family home without any of the maintenance. Contact Corwin Partners for a private appointment at Sales Gallery at 2977 N Clybourn.

2235 W Oakdale Avenue Unit #20-B, Chicago
$300,500
5 Beds ⋅ 2 Baths ⋅ 12654228 MLS ⋅ CONTINGENT Status
Welcome to this charming two-unit property in a rapidly revitalizing Englewood neighborhood. With an affordable list price, this property is brimming with potential. This building offers a fantastic opportunity for investors or those looking to live in one unit and collect rent from the other! There is separate heating, which is great for maximizing rental income. The second-floor unit is move-in ready, while the first-floor unit has a long-term tenant. The area has excellent walkability throughout the community, good transportation options, and many new things happening for accessibility in the community. Don't miss out on this incredible opportunity!

6209 S Justine Street, Chicago
$465,000
5 Beds ⋅ 3 Baths ⋅ 12640821 MLS ⋅ ACTIVE Status
Beautiful, well-maintained home with a spacious, functional layout and modern touches throughout. The main level features an inviting living area filled with natural light, an updated kitchen with ample cabinet space, and a separate dining area perfect for everyday living and entertaining. The bedrooms are generously sized, and the master bedroom has its own private bathroom. The finished lower level provides comfort and flexibility, adding valuable extra living space ideal for a family room, recreation area, home office, or gym. Enjoy the convenience of several freshly updated bathrooms, a dedicated laundry area, and lots of storage throughout the home. The backyard provides a wonderful outdoor space perfect for get-togethers, relaxing, or summer fun. Nestled in a sought-after neighborhood near parks, schools, shopping, dining, and major highways. A move-in-ready home that offers something for everyone in the family!

4951 W Concord Place, Chicago
$229,000
5 Beds ⋅ 3 Baths ⋅ 12651650 MLS ⋅ ACTIVE Status
Welcome to this spacious and beautifully updated 6-bedroom, 3-bath home offering an abundance of living space and endless possibilities. Featuring numerous recent updates throughout, this home combines comfort, functionality, and style. Enjoy generously sized bedrooms, updated bathrooms, a modernized kitchen, and expansive living and entertaining areas perfect for large households or multi-generational living. The ample square footage provides flexibility for a home office, gym, playroom, or guest space. Natural light fills the home, creating a warm and inviting atmosphere. Move-in ready with room to grow - this is a must-see property!

135 W 109Th Place, Chicago
$280,000
5 Beds ⋅ 2 Baths ⋅ 12652010 MLS ⋅ CONTINGENT Status
A charming, recently refreshed 2-flat frame property offering versatility for both homeowners and investors. With 5 total bedrooms and 2 full bathrooms, each unit delivers a comfortable, functional layout ideal for long-term living or steady rental income. The first-floor unit features 3 well-proportioned bedrooms and 1 bath, providing ample space for families or reliable tenants. The second-floor unit offers 2 spacious bedrooms and 1 bath, making it an excellent option for an owner occupant or an easy to rent unit. Live in one unit and lease the other to help with your mortgage and build equity faster - a smart path to becoming your own landlord. Whether you're expanding your portfolio or stepping into homeownership, this property is designed to work for you. A move in ready opportunity in a desirable location at an accessible price point is hard to find. Don't miss your chance to secure a solid, income producing asset with room to grow.

307 E 136Th Place, Chicago
$520,000
5 Beds ⋅ 3 Baths ⋅ 12647778 MLS ⋅ ACTIVE Status
Located in the sought-after Belmont Cragin neighborhood, this well-maintained property offers an incredible opportunity for both owner-occupants and savvy investors alike! Situated in the desirable 60639 area, this versatile building features spacious living arrangements, functional layouts, and excellent income potential. The main dwelling offers 3 generously sized bedrooms, 1 full bathroom, a large L-shaped living room perfect for entertaining, ample kitchen space with abundant cabinetry, and a separate eating area off the kitchen. Radiant heated floors add comfort throughout, while the covered rear deck provides a great outdoor retreat. The second floor features a very large 1-bedroom, 1-bath layout with a spacious living room, separate dining/eating area off the kitchen, radiant heat within the walls, and its own covered deck. This unit is tenant occupied, making it ideal for immediate rental income. The recently updated finished basement expands the living space even further with an additional bedroom, full bathroom, kitchenette, dining area, and a comfortable family/living room featuring a fireplace. Additional basement highlights include a large walk-in closet, oversized laundry area, mechanical room with workout/flex space, and a convenient mud room with rear entry access. Outside, enjoy a large fenced yard perfect for entertaining, gardening, or pets, along with a 2-car garage for added convenience. Ideally located near shopping, dining, and public transportation, this property combines space, flexibility, and strong investment potential in one of Chicago's established neighborhoods. This is a legal non-conforming 2 unit property. Don't miss this exceptional opportunity!

2705 N Monitor Avenue, Chicago
$4,550,000
5 Beds ⋅ 6 Baths ⋅ 12643241 MLS ⋅ ACTIVE Status
Situated on one of Lincoln Park's most coveted tree-lined streets just steps off Armitage, this exceptional newer construction 5-bedroom, 5.1-bath home seamlessly blends sophisticated modern design with thoughtful functionality in an unbeatable location. Built in 2019, the residence is filled with natural light and features soaring ceilings and dramatic floor-to-ceiling windows throughout every level. A beautiful entry foyer welcomes you into an elegant, sun-filled living and dining space that feels both refined and inviting. The sleek chef's kitchen showcases striking European cabinetry, premium appliances, an oversized island with built-in shelving, and a clean contemporary aesthetic perfect for both everyday living and entertaining. Just off the kitchen, the spacious rear family room features custom built-ins, marble tile detail, and an electric fireplace, while a fully opening accordion-style glass door creates a seamless transition to the private outdoor patio. The space also offers the opportunity to build out an incredible garage rooftop deck. The second level offers three generously sized ensuite bedrooms, including a luxurious primary suite flooded with natural light through oversized windows. The spa-inspired primary bath features a floating soaking tub, steam shower, dual vanity, and a serene retreat feel. The top floor provides incredible flexibility with an additional large bedroom featuring floor-to-ceiling windows, another full bath, and a bright oversized family room that opens directly onto an expansive rooftop terrace ready to be transformed into your dream outdoor oasis. The lower level offers a large recreation room perfect for cozy nights in or entertaining, along with an additional bedroom, full bath, mudroom entry, and dedicated laundry room. A second laundry area is conveniently located on the bedroom level upstairs. Additional highlights include surround sound throughout, integrated smart home technology for seamless control, and a two-car garage. Ideally located just steps from parks, restaurants, boutiques, and everything Lincoln Park has to offer, this home delivers exceptional modern living on one of the neighborhood's premier streets.

1944 N Fremont Street, Chicago
$475,000
5 Beds ⋅ 3 Baths ⋅ 12650081 MLS ⋅ ACTIVE Status
Recently updated very large home in fast appreciating area. Upon entering, the large foyer welcomes you to an open concept layout combining living and dining room. Updated kitchen has new cabinets and quartz countertops. 2 bedrooms and a full bathroom complete the first floor. Second floor has master bedroom with walk in closet and additional family room. Large finished basement with exterior access. Conveniently located seconds from 290. Close to downtown and medical district. Numerous new construction and rehabs all around This home has multiple cosmetic updates including new floors, paint, lights, kitchen and bathrooms. Home is being sold as-is.

2720 W Harrison Street, Chicago
$389,999
5 Beds ⋅ 4 Baths ⋅ 12648972 MLS ⋅ ACTIVE Status
Welcome Home! This large beautifully rehabbed single-family home featuring 5 bedrooms and 4 bathrooms. This spacious property offers hardwood floors throughout the first and second levels, with ceramic tile in the finished basement. The finished basement includes 1 bedroom, 1 full bathroom, and a family room, providing additional living space for guests, extended family, or entertaining. The home has been renovated from top to bottom with major updates including a new kitchen, new bathrooms, new electrical, new plumbing, new windows, 2 furnaces, and 2 water heaters. All work was completed with permits. The home also features an exceptional primary bedroom with a private attached bathroom and a generously sized closet for extra storage. Appliances were purchased after the listing photos were taken. FHA Approved! Schedule a showing today! Seller is very motivated and all offers will be considered.

6640 S Champlain Avenue, Chicago
$124,900
5 Beds ⋅ 3 Baths ⋅ 12645541 MLS ⋅ CONTINGENT Status
*** MULTIPLE OFFERS RECEIVED - HIGHEST AND BEST CALLED FOR DUE MONDAY 7.13.26 AT NOON* - Attention investors and savvy owner occupants looking for a huge value-add opportunity in the red-hot Greater Grand Crossing neighborhood! This house is much larger than it looks and includes 5 bedrooms, 2.5 baths and a detached garage. The property needs some TLC and is being sold AS-IS. Alleged Code Violations from a 2022 Conservation Inspection Attached. Home will not pass FHA.

7047 S Eberhart Avenue, Chicago
$1
5 Beds ⋅ 2 Baths ⋅ 12648278 MLS ⋅ AUCTION Status
This two unit traditional style home built in 1920 offers 6 bedrooms and 2 bathrooms with approximately 2250 square feet of living space on a .13 acre lot. The foreclosure deed has been recorded, allowing for shorter closing timelines. Please be advised that this property has code violations from the City of Chicago. These violations would be transferred to the new owner. No Buyer Premium on this property. The buyer has the right to select their own title/closing company. The buyer is responsible for all closing costs in this transaction. It is a criminal offense to trespass on this property. Sold As Is. Seller does not provide survey. Room sizes are estimated and unverified. Xome Auction. *Property not for rent.*

11806 S Parnell Avenue, Chicago
$399,000
5 Beds ⋅ 3 Baths ⋅ 12648217 MLS ⋅ CONTINGENT Status
Great opportunity to own a solid brick 2-flat in the highly sought-after Pilsen neighborhood! This property features 2 legal units plus a finished attic offering additional living space with an extra room. In total, the home offers 5 bedrooms and 3 full bathrooms, making it ideal for owner-occupants, multi-generational living, or investors seeking rental income potential. The property also includes a very solid 2-car garage, plus 2 additional exterior parking spaces in the rear, along with a private patio area between the home and garage perfect for outdoor enjoyment. Conveniently located just steps from the Pink Line train with easy access to downtown Chicago, shopping, restaurants, schools, and transportation. This is a fantastic opportunity for a starter home or investment property with great upside potential. Property needs some TLC but offers strong bones and endless possibilities. Property is being sold AS-IS. Don't miss your chance to own in one of Chicago's most vibrant neighborhoods - schedule your showing before it's gone!

2123 W Cullerton Street, Chicago
$450,000
5 Beds ⋅ 3 Baths ⋅ 12645662 MLS ⋅ CONTINGENT Status
Excellent investment opportunity in a desirable Northwest Chicago neighborhood. This fully leased, well-maintained building generates $3,500 per month in gross rental income ($42,000 annually), with an estimated net operating income of $26,613.52 and a current cap rate of approximately 5.91%. With only a modest 10% increase in rents, the cap rate would exceed 6.5%, presenting strong upside potential. Additional income is generated from the basement coin laundry (one washer and one dryer), producing approximately $400-$500 annually. Recent improvements include a new roof (2019), new front porch (2019), garden unit remodeled (2018), and Unit 1 remodeled (2020). The property features hardwood floors in the first and second floor units, separate furnaces, and separate electric meters. Units #1 and #2 have tenants paying all utilities, while utilities are included in the rent for the garden unit. The building is fully rented with well-screened, reliable tenants, and units are clean and well-maintained. Additional highlights include easy street parking, outdoor storage sheds, a large fenced yard with a concrete patio, and coin laundry in the basement for supplemental income. Seller makes no representation regarding the legality of the third (garden) unit.

3301 N Ozanam Avenue, Chicago
$180,000
5 Beds ⋅ 2 Baths ⋅ 12646324 MLS ⋅ ACTIVE Status
Check out this spacious 5 bedroom 2 bath home . The Main level offers Hardwood floors, spacious living room, dining room. eat-in kitchen, and full bathroom. Finished attic with two added bedrooms. Nice vintage features such as high ceilings, wood wind trim. Two car garage, fenced yard, good area for transportation.

8728 S Carpenter Street, Chicago
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