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2-flats For Sale In Chicago IL

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Newest 2-flats Properties In Chicago

$583,000
4 Beds 2 Baths 12764178 MLS NEW Status
Classic Chicago two-flat offering a great combination of vintage character, spacious floor plans, and income potential. Each unit features 2 bedrooms, 1 full bath, a separate living room and dining room, kitchen, and enclosed sunroom, providing generous living space and flexible room configurations. The property retains attractive original details, including hardwood floors, substantial wood trim and doors, and a distinctive stained-glass window. Large windows provide excellent natural light throughout both units. The kitchens offer ample cabinet and counter space, while the bathrooms are functional and well maintained. The full unfinished basement provides extensive storage, laundry facilities, mechanicals, and additional possibilities for the new owner. A detached two-car garage is another significant benefit-especially for a Chicago two-flat. This property provides flexibility for an owner-occupant, extended-family arrangement, or investor. Live in one unit while generating rental income from the other, or maintain both apartments as rental units. With two well-proportioned apartments, separate living and dining spaces, sunrooms, a full basement, and a two-car garage, this is a versatile property with plenty of potential. Outstanding Jefferson Park location! Enjoy the convenience of a highly walkable neighborhood with shopping, restaurants, parks and everyday amenities nearby. Excellent transportation options include nearby CTA bus service plus convenient access to the Jefferson Park Transportation Center offering CTA Blue Line, Metra and Pace service, providing easy connections to downtown Chicago, O'Hare and the northwest suburbs. Commuters will also appreciate convenient access to the Kennedy and Edens Expressways. Outdoor recreation is plentiful, with neighborhood parks, Caldwell Woods, LaBagh Woods and other forest-preserve areas nearby. This location offers an appealing combination of a residential neighborhood setting with outstanding access to transportation and city amenities. Property Highlights: Two units * 2 bedrooms/1 bath per unit * Separate living and dining rooms * Kitchen in each unit * Enclosed sunroom in each unit * Hardwood floors and vintage woodwork * Full unfinished basement * Laundry area * Detached 2-car garage * Excellent natural light. SOLD AS IS.

Chicago

$1,395,000
6 Beds 6 Baths 12699701 MLS NEW Status
Introducing a stunning new construction two-flat in the heart of historic Pilsen. Designed with flexibility and lifestyle in mind, this beautifully crafted property is ideal for multigenerational living, owner-occupants seeking rental income, or savvy investors looking for a standout opportunity in one of Chicago's most vibrant neighborhoods. The garden unit is over 1200 sf offering 2 bedrooms and 2 full baths. The duplex up is over 2430 sf and lives like a single-family home, including 4 bedrooms and 3.5 baths. Both homes are filled with natural light and complemented by beautifully designed and well-proportioned kitchens with open concept large family rooms connected to outdoor space, in-unit laundry and generous storage. Both kitchens include white oak cabinetry, quartz countertops, decorative backsplashes and stainless-steel appliances including beverage centers. Abundant private outdoor space offers true indoor/outdoor living including gas, electricity, and water hookups. The garden unit has 2 outdoor living spaces including the shared backyard and private front patio while the duplex unit highlights vaulted ceilings with a large custom designed enclosed deck off the family room extending the living and entertaining space adding a dramatic finishing touch. The back patio offers a retreat off the primary bedroom with city skyline views. With excellent closet space, refined design details, and quality craftsmanship throughout, these homes deliver both comfort and sophistication. Enjoy the best of Pilsen just outside your door-renowned dining, easy access to transportation, neighborhood events, and the unmistakable energy of the community. This is a rare opportunity to own a thoughtfully designed, expertly built new development in an unbeatable location.

1118 W 19Th Street, Chicago

$579,000
4 Beds 3 Baths 12764061 MLS NEW Status
NEW CITY! If you lived here-you'd be enjoying a healthier, more affordable, and comfortable lifestyle with less maintenance! Come your our MODEL HOME in what will be Chicago's largest sustainable community. Excellent location, minutes from the loop, Midway, transit and just a block from beautiful Historic Sherman Park. Greenline Homes, an award-winning developer, is transforming this neighborhood into a sustainable community with homes that truly work for their owners. Perfect for first-time buyers! Rental income helps make your home more affordable, and it's great for multigenerational buyers who want accessibility without sacrificing their lifestyle. This brand-new all-electric two-flat blends beautiful design, thoughtful layouts, cutting-edge building science, and the best materials and equipment available. On the main level, the primary duplex-up unit features a versatile bonus room, perfect for a high-end home office, 3rd bedroom, or recreation room. Upstairs, a private rear balcony, large enough for gatherings and dining, is directly off the great room, creating a seamless indoor-outdoor living experience. The stunning ADA-accessible first-floor unit offers a spacious retreat, ideal for multi-generational living or generating high-value rental income to boost affordability. No compromises here-custom cabinetry, designer quartz, and induction cooking in a home designed for the future. Triple-pane windows ensure ultimate thermal comfort, and a fully paid-for solar PV system means near-zero utility costs without sacrificing style. The super insulated walls and roof make for a library-quiet interior. Plus, an energy recovery ventilator keeps fresh, filtered air flowing 24/7, even when the windows are closed, so you can still enjoy comfort and efficiency. Every detail, from the premium Hardie Board exterior to the EV-ready garage and gated intercom security, is designed for effortless, low-maintenance living. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. And the best part? More houses to come next door...

5236 S Bishop Street, Chicago

$1,275,000
6 Beds 3 Baths 12763197 MLS NEW Status
Charming Andersonville 2-Flat with Owner-Occupant & Investment Potential Welcome to 1639 W Rascher Ave, a charming and versatile two-flat located in the heart of Chicago's highly sought-after Andersonville neighborhood. This classic Chicago property offers an excellent opportunity for an owner-occupant, multigenerational household, or investor looking to own in one of the city's most desirable and walkable communities. The property features spacious living areas, classic Chicago character, and a flexible layout that provides the opportunity to live in one unit while generating rental income from the other. With approximately 2,456 square feet of living space and a generously sized lot, there is plenty of room to make this property your own. Enjoy everything Andersonville has to offer just outside your door-from locally owned restaurants, cafes, shops and boutiques to neighborhood parks, community events and easy access to the lakefront. The surrounding residential streets offer a wonderful balance of city convenience and neighborhood charm, making this an appealing location for both families and professionals. The property's two-flat configuration provides multiple possibilities for the next owner: live in one unit and rent the other, accommodate extended family, or maximize its investment potential. Its location, size, and flexible layout make this a unique opportunity to own a piece of one of Chicago's most vibrant neighborhoods. Come experience the character, convenience, and lifestyle that make Andersonville such a special place to call home.

1639 W Rascher Avenue, Chicago

$1,150,000
5 Beds 6 Baths 12763441 MLS NEW Status
Welcome to this exceptional Greystone vintage 2-unit building with a garden apartment on the lower level - offering 5 bedrooms, 5 full bathrooms, and 1 half bathroom, perfectly blending classic Chicago charm with modern comfort. Featuring beautiful landscaping, a fenced backyard, and thoughtfully designed living spaces, this remarkable property presents an outstanding opportunity for both homeowners and investors. A stunning hardwood staircase welcomes you through the main entrance, providing access to both the first- and second-floor units. Let's begin with the second-floor residence. As you enter, you're greeted by a bright and spacious living room, highlighted by a beautiful English skylight lantern above the foyer and oversized windows that fill the home with abundant natural light. Located just off the living room, the primary suite offers a private retreat with a separate sitting area, generous closet space, direct access to a private balcony, and large windows that create a warm and inviting atmosphere. On the opposite side of the living room, the second bedroom features a walk-in closet and ample living space. The unit includes two full bathrooms-one with a luxurious walk-in steam shower and the other with a relaxing soaking tub. Conveniently located between the bedrooms, the dedicated laundry room adds everyday comfort and functionality. Toward the rear of the home, the open-concept family room and kitchen create the perfect gathering space, centered around a cozy fireplace with both gas and wood-burning options. The kitchen is beautifully appointed with stainless steel appliances, a large center island with breakfast bar seating, pantry storage, and expansive windows that surround the space with exceptional natural light. The first-floor unit mirrors the upper-level layout, offering incredible flexibility for multi-generational living or rental income. It features its own fully equipped kitchen, two full bathrooms, a dedicated laundry room, and an added layer of security with alarm sensors installed on every window. From the rear staircase, you'll find access to the basement studio unit. Before entering the studio, you'll pass a spacious recreation room, utility area, and a separate laundry room dedicated exclusively to the lower-level residence. Inside the studio, you'll find a thoughtfully designed living space featuring a full kitchen with stainless steel appliances, a microwave, air fryer, and range hood. The studio also includes one full bathroom, one half bathroom, and generous closet space, creating a comfortable and functional living arrangement that's perfect for guests, extended family, or rental income. The rear staircase also provides convenient access to the rooftop, the first-floor unit, and the second-floor residence, making movement throughout the building both practical and efficient. Designed with long-term comfort and peace of mind, the property is equipped with multiple tankless water heaters, multiple zoned furnaces, multiple sump pumps, and a comprehensive security system, showcasing the exceptional care and quality invested throughout the home. Step outside to enjoy the beautifully landscaped, fenced backyard featuring a brick paver patio, mature landscaping, and multiple outdoor seating areas-an ideal setting for entertaining family and friends or simply relaxing outdoors. Conveniently located near public transportation, bus routes, restaurants, grocery stores, shopping, and everyday conveniences, this exceptional Greystone offers the perfect combination of timeless Chicago architecture, modern functionality, and outstanding investment potential. Don't miss this rare opportunity to own a versatile, meticulously maintained multi-unit property that seamlessly blends historic character, modern upgrades, and exceptional income potential-all in one of Chicago's most desirable neighborhoods.

4448 N Tripp Avenue, Chicago

$649,900
6 Beds 3 Baths 12759675 MLS NEW Status
GORGEOUS CLASSIC CHICAGO GREYSTONE 2-FLAT - BOTH RESIDENTIAL UNITS COMPLETELY REHABBED IN 2025! Both units have been beautifully renovated, while many major systems and exterior components have also been replaced or upgraded. Major 2025-2026 improvements include a NEW ROOF, WINDOWS, FURNACES, CENTRAL A/C, WATER HEATER, ELECTRICAL, PLUMBING, SIDING/EXTERIOR, GUTTERS & DOWNSPOUTS, SUMP PUMP, SEWER LINE, and BASEMENT/FOUNDATION WATERPROOFING. New drywall was installed throughout both units. Each unit features new kitchens with cabinets, countertops and appliances, remodeled bathrooms, updated flooring, fresh paint, new lighting, fixtures, doors and trim. New refrigerators, ranges, dishwashers, washers and dryers are included, along with smart thermostats and security cameras. The property also offers a rear deck, extra-deep backyard and parking, plus an unfinished basement with front and rear access, good ceiling height and separate heating. The basement provides excellent storage and flexible-use space, with potential for a future garden unit, subject to City of Chicago zoning, building-code and permitting requirements. Ideally located in East Garfield Park, just minutes from the United Center, Green Line, I-290, Garfield Park Conservatory, parks and Downtown Chicago. A wonderful opportunity to own a classic Chicago Greystone with two beautifully rehabbed residential units, major updates already completed, a spacious lot, and an unfinished basement with future potential. A great choice for an owner-occupant or investor!

3234 W Fulton Boulevard, Chicago

$1,199,000
5 Beds 3 Baths 12758512 MLS NEW Status
Outstanding opportunity to purchase a 2 flat building on a picturesque residential corner with 2 car parking garage and incredible outdoor space 3657 N. Hermitage Avenue. Prime Lakeview Location! This desirable two-flat is located on a quiet, tree-lined residential street in the heart of Chicago's sought-after Lakeview neighborhood. The property offers an excellent combination of classic Chicago character, convenient city living, and strong neighborhood appeal. Enjoy easy access to the Southport Corridor, Wrigleyville, North Center, Roscoe Village and Lincoln Park, with an abundance of restaurants, cafes, shopping, entertainment and everyday conveniences nearby. Southport Avenue, Lincoln Avenue, Belmont Avenue and the Wrigleyville entertainment district are all within easy walking or biking distance. Residents also enjoy convenient access to neighborhood parks, playgrounds and Chicago's lakefront recreational opportunities. Schools: Chicago Public Schools District 299, including Hamilton Elementary School and Lake View High School. With its highly walkable location, nearby public transportation, restaurants, shopping, parks and entertainment, 3657 N. Hermitage Avenue is an excellent opportunity for an owner-occupant or investor seeking a two-flat in one of Chicago's most desirable North Side neighborhoods. This is a well-maintained property with a new garage roof. The property is available for owner occupants and investors; basement can also be converted to a 3rd unit which will be financially benefit a new owner

3657 N Hermitage Avenue, Chicago

$1,200,000
7 Beds 2 Baths 12757528 MLS NEW Status
A rare opportunity in Chicago's desirable Ravenswood area! Built in 1898, this classic Victorian 2-flat with Queen Anne architectural influences makes a striking first impression with its steep front-facing gable, asymmetrical facade, projecting second-floor bay, tall, narrow proportions, decorative brackets and trim beneath the gable and eaves, and distinctive shingle treatment at the peak.This substantial, owner-occupied vintage 2-flat sits on an exceptionally deep 25' x 174' lot and offers approximately 3,445 square feet of living space-about 1,722 square feet per floor-plus a full high-ceiling attic and full basement. 10 foot ceilings on both floors. 8-12 foot ceilings in the attic. Loaded with original character, the home features beautiful hardwood floors, high ceilings on both levels, vintage pocket doors, substantial original trim and moldings, and custom built-ins in the dining room. The first-floor residence offers three generously sized bedrooms, a large kitchen footprint and decorative faux fireplace. The second floor features four nicely sized bedrooms and a wood-burning fireplace. Beyond the two main living levels, the property offers tremendous additional space. The full attic has impressive ceiling height, while the full basement also features high ceilings and two separate entrances. Outside, the unusually deep lot provides a large, open grassy backyard with plenty of room to enjoy. Zoned RS-3, this is a property with tremendous potential and possibilities. Preserve and update it as a spacious 2-flat, explore conversion to a grand single-family residence, or investigate other potential configurations such as duplex-up/duplex-down or condominium conversion, subject to zoning and City of Chicago approvals. This is an opportunity for a buyer with vision to restore, renovate and reimagine a large vintage Ravenswood property with wonderful architectural details, substantial square footage and an exceptional lot. Property is being sold strictly "as-is." Most contents currently in the property will remain and are included with the sale, with the exception of certain personal items the seller will remove prior to closing.

4426 N Damen Avenue, Chicago

$1,200,000
5 Beds 3 Baths 12748261 MLS NEW Status
Located in the heart of Logan Square, this classic brick two-flat underwent a full gut renovation in 2020, thoughtfully preserving its original architectural details while introducing updated finishes, modern systems and functional living spaces. The result maintains the vintage charm of a traditional Chicago two-flat while offering the comfort and convenience of a fully renovated home. The first-floor duplex-down offers 3 bedrooms and 2 full baths across two levels. The main level features a living room with the original fireplace and mantel, a dedicated dining room, two bedrooms, a full bath and a fully appointed kitchen. The lower level expands the living space with a spacious family room, perfect as a media room, home office or additional flex space, along with a third bedroom and second full bath. The second-floor unit offers 3 bedrooms and 1 full bath with a comfortable, functional layout and its own original fireplace mantel, preserving another piece of the home's vintage character. Both units feature enclosed porches, central heat and air conditioning, and updated interiors that complement the building's original details. A shared laundry area is conveniently located on the lower level, and the property also includes a shared backyard and detached 2-car garage. Ideally situated near Logan Square's restaurants, cafes, shopping, entertainment, parks and neighborhood amenities, this turnkey two-flat offers versatility for an owner-occupant, investor or multigenerational living. With two updated units, flexible living spaces and a prime neighborhood location, this is a unique opportunity to own a classic Chicago two-flat that has already undergone a comprehensive renovation. Photos from 2020 renovation, new photos coming soon!

2428 N Rockwell Street, Chicago

$530,000
5 Beds 3 Baths 12759258 MLS ACTIVE Status
Welcome to this well maintained two unit property in the heart of Bronzeville, offering a great opportunity for an owner occupant or investor. The first floor apartment is a cozy two bedroom, one bath walk up with its own in unit washer and dryer and a comfortable layout that makes it easy to call home. Upstairs, the spacious duplex lives more like a single family home. The main level features hardwood floors, a generous living area, half bath, in unit laundry, and an eat in kitchen with an island plus plenty of room for a dining table. Upstairs, you'll find brand new carpet, three bedrooms, a full bath, separate linen closet, and a spacious primary bedroom with vaulted ceilings and its own private balcony. Out back, enjoy a private fenced yard with a deck just off the kitchen, perfect for relaxing, grilling, or entertaining. A two car garage adds even more convenience, and with separate utilities for each unit, the property is set up well for both owner occupants and investors. Located in historic Bronzeville, you'll be surrounded by a neighborhood known for its beautiful architecture, rich culture and history, while enjoying convenient access to public transportation, the lakefront, parks, restaurants, and downtown Chicago. Live in the duplex and let the second unit help with your expenses, bring extended family closer while maintaining separate living spaces, or add a solid two unit property to your investment portfolio. There are plenty of possibilities here. These units are NOT listed for rent on any website or Facebook marketplace.

631 E Bowen Avenue, Chicago

$1,100,000
5 Beds 4 Baths 12757167 MLS ACTIVE Status
Rarely available all-brick 2-unit building in an unbeatable Wicker Park location, just steps from Colectivo Coffee! Situated on a 24' x 120' lot, this property offers more than 1,300 SF per floor, good bones, vintage curb appeal, generous ceiling heights, excellent outdoor space, and a highly desirable layout. Zoned RT-4 and not located in a landmark district. The tenant occupied top-floor 2BD/1BA simplex features approximately 10' ceilings, beautiful parquet wood flooring, an exceptionally spacious living/dining area, covered private rear deck, and a massive bedroom easily accommodating a king-size bedroom set plus additional furnishings. Newer in-unit washer/dryer in a dedicated closet, tankless hot water, furnace, and central A/C. The 3BD + den/3BA duplex-down is ready for immediate occupancy and offers an impressive blend of vintage character and thoughtful updates. The upper level showcases exposed brick and timber details in the front living area, approximately 10' ceilings, and a dramatic skylight that floods the open-concept kitchen with natural light. The enormous kitchen offers an extraordinary amount of cabinetry and counter space, with beautiful granite countertops, plus a pantry closet. The oversized primary suite features abundant closet storage and a jetted tub, while the second full bath on this level also includes a jetted tub. Upper-level flooring has just been refinished. The newly finished lower level features quality new vinyl plank flooring, a laundry room with oversized side-by-side washer/dryer, a third full bathroom with steam shower and body sprays, and a versatile rear bonus room. The middle walk-through bedroom includes an enormous walk-in closet. A new comprehensive waterproofing system (drain tile and sump pump) was added when the owner created the duplex unit about a decade ago and the basement has been bone dry. Each unit has its own furnace, central A/C, and in-unit laundry. Incredible oversized backyard, extra-wide 2-car garage, and classic all-brick facade with serious vintage curb appeal. Despite being on a main road, street noise is remarkably well contained inside. An exceptional opportunity to own a distinctive Wicker Park 2-flat with strong owner-occupant and investment appeal, just approximately 100 feet north of Colectivo Coffee and surrounded by the neighborhood's renowned restaurants, shops, nightlife, and transportation.

1219 N Damen Avenue, Chicago

$650,000
5 Beds 4 Baths 12755646 MLS ACTIVE Status
WHY BUY ONE LIVING SPACE WHEN YOU CAN HAVE TWO? BRAND-NEW CONSTRUCTION WOODLAWN DUPLEX designed for luxury living, house hacking, and income potential! Live upstairs and let the garden unit help reduce your mortgage-or maximize the property's rental potential in one of Woodlawn's most exciting locations. UNIT 1 offers 3 spacious bedrooms and 2.5 baths with HARDWOOD FLOORS THROUGHOUT. Enjoy an impressive overly sized open layout with quartz countertops, waterfall island, custom wet bar with glass rinser, fireplace, smart toilets, and high-end washer and dryer per unit. The spacious primary suite features its own private bath with double vanities. The GARDEN UNIT features 2 bedrooms and 1 bath with its own open modern open kitchen, living area, and high end washer/dryer in unit. Ideal for long-term rental income, extended family, or potential short-term rental use where permitted. Short-term rentals in the surrounding area can command strong rates, with demand supported by nearby attractions and institutions. LOCATION MATTERS! Minutes from the OBAMA PRESIDENTIAL CENTER, University of Chicago, Jackson Park, Museum of Science and Industry, Hyde Park, the lakefront, and convenient transportation. More upgrades include SOLAR PANELS that you ACTUALLY OWN to help reduce utility expenses, tankless hot water, a HUGE REAR DECK built for entertaining, and a BRAND-NEW 2-CAR GARAGE. NEW CONSTRUCTION. TWO LIVING SPACES. INCOME POTENTIAL. PRIME WOODLAWN LOCATION. GRANTS ASSISTANCE MAY BE AVAILABLE for qualified buyers. Schedule your private showing today!

6547 S Evans Avenue, Chicago

$549,900
5 Beds 3 Baths 12755567 MLS ACTIVE Status
Welcome to one of the largest residential 2-flat properties you'll find in the highly sought-after North Lawndale neighborhood! This property has been fully rehabbed, with the renovation completed in August 2026, offering buyers the opportunity to own a beautifully updated multi-unit property with modern finishes and extensive improvements. Situated on three city lots, this unique property offers an abundance of land and flexibility rarely found in a multi-unit setting. The property sits on one lot with an additional lot on each side, providing exceptional outdoor space and plenty of room for parking, recreation, expansion, or storage. Business owners with multiple vehicles, work trucks, equipment, or additional parking needs-this could be the ideal property for you! The expansive lot configuration provides valuable space that is difficult to find in the city. Inside, the property features two beautifully remodeled 2-bedroom units, each offering one full bath, a kitchen, and a modern open-concept layout. The second-floor unit is duplexed into the attic, creating additional living flexibility and making the space ideal for an in-law suite, extended family, guests, or other living arrangements. The attic includes its own kitchen and bathroom while sharing central heat with the second-floor unit. The first- and second-floor living spaces each feature their own individual furnace and central heating, providing separate heating systems for each unit. All living areas have been thoughtfully remodeled with modern finishes and an inviting open-concept design. Located in the rapidly developing North Lawndale community, this property offers convenient access to Chicago's Medical District, downtown Chicago, major highways, dining, entertainment, and nightlife. Approximately a 15-minute drive to the Medical District and 25 minutes to downtown, making this an excellent location for both residents and commuters. Whether you're an investor looking for a versatile multi-unit property, an owner-occupant seeking additional living space, or a business owner in need of substantial parking and land, this property offers possibilities that are hard to find. Three lots. Two remodeled units. Recently completed rehab. Exceptional flexibility and space. Don't miss this opportunity-schedule your showing today! This one won't last long!

2248 S Kolin Avenue, Chicago

$579,999
4 Beds 3 Baths 12744009 MLS ACTIVE Status
Excellent opportunity to own a well-maintained 2-flat in the highly desirable Jefferson Park neighborhood, offering strong rental potential and an ideal setup for owner-occupants. This classic Chicago multi-unit features two spacious units, a finished basement, and shared laundry, making it a versatile investment in one of the city's most commuter-friendly areas. The first-floor unit offers 2 bedrooms and 1 bathroom with hardwood floors throughout, a bright and spacious living room that flows into a separate dining room, and a well-appointed kitchen with an eat-in breakfast area. This unit also includes central heating and air conditioning, providing year-round comfort. The second-floor unit features 1 bedroom and 1 bathroom with 9-foot ceilings. All wood floors throughout the first/Second floor. The layout includes a large living room, separate dining room, and a spacious kitchen with a walk-in pantry, along with a generous bedroom featuring a large walk-in closet. The finished basement offers additional living, recreation, or storage space and includes shared laundry and mechanicals, including the furnace, A/C, and water heater. Basement features full bedroom and bathroom. Significant exterior improvements include a newer roof, windows, siding, 2 car garage, concrete patio, and privacy fence, creating a low-maintenance investment with appealing outdoor space. Located in the heart of Jefferson Park, the property offers exceptional access to transportation and neighborhood amenities, including nearby **CTA Blue Line stations and multiple Metra lines for easy commuting to downtown Chicago. Residents are also within walking distance to everyday conveniences such as Mariano's, Target, and Starbucks, with quick access to Interstate 90 and Interstate 94. Jefferson Park is known for its strong rental demand, neighborhood charm, and unmatched transit connectivity, making this property an excellent choice for investors seeking steady income or buyers looking to live in one unit while generating rental income from the other. Home has a 2 car garage and parking pad next to garage. Fully fenced in yard. Click on 3d tour to walk though unit. 1st floor unit availabe for owner occupancy now. Do not miss this chance to live and have others pay your mortage!

5037 W Winona Street, Chicago

$599,000
6 Beds 2 Baths 12743011 MLS ACTIVE Status
Beautifully Maintained Spacious Two-Unit | Double Lot | 2-Car Garage Nestled on a quiet, tree-lined street in the heart of the city, this spacious two-unit property offers an incredible combination of comfort, versatility, and outdoor space. With two generously sized 3-bedroom units, this property is ideal for an owner-occupant, multi-generational living, or an investor looking to add a strong income-producing property to their portfolio. Each unit features 3 bedrooms, 1 full bathroom, a large dining room, and a spacious kitchen, with private entrances accessible from both the front and rear of the property. The property also offers a full walk-out basement with a dedicated laundry room, workshop, and abundant storage space. An expansive unfinished attic provides even more storage or the opportunity to create additional living space tailored to your needs. Enjoy even more usable space with the enclosed rear porch. The second-floor unit has been rehabbed, featuring new cabinets, appliances, and flooring. The first-floor unit features beautiful hardwood flooring throughout, along with central air and heat, great crown molding throughout and lots of natural light. Outside, the property truly stands out. Situated on a double lot, there is plenty of room to enjoy the outdoors, with a two-car garage, side driveway, additional guest parking, rear patio, and spacious backyard. With its generous floor plans, extensive storage, private entrances, updated units, and exceptional lot size, this property offers tremendous potential and is sure to attract attention. Don't miss your opportunity-schedule your showing today!

1936 N Tripp Avenue, Chicago

$549,999
5 Beds 5 Baths 12743055 MLS ACTIVE Status
Thoughtfully composed for modern ownership, 1433 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 and Downtown Chicago. More than a new build, 1433 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 1433 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.

1433 S Trumbull Avenue, Chicago

$699,000
5 Beds 4 Baths 12740618 MLS ACTIVE Status
Live large, live green, and let your investment work for you. As the first of its kind ever built in North Lawndale, this two-unit marks the dawn of the next generation of housing in the neighborhood - a solar-powered building designed for an owner who wants the space and feel of a single-family home with the built-in cash flow of a rental unit. The Owner's Duplex-Up: Spanning two full floors, this 3-bedroom, 2.5-bath duplex-up lives like a detached single-family home. Soaring 9' ceilings and an open, light-filled layout set the stage for the elegant chef's kitchen with floor-to-ceiling cabinetry, quartz countertops, and a sleek induction range, anchored by a massive 10' island and glass herringbone backsplash. The living room centers around a fireplace framed by built-in glass shelving, while crown molding with LED up-lighting adds a refined finishing touch throughout. Just off the living room, the dining area is made for hosting - a dry bar, wine cooler, and floating shelves make every gathering effortless. Custom built-in mudroom cabinetry keeps everyday life organized as you walk in the door. This is a home designed for how people actually live - spacious, efficient, and thoughtful. The Garden Investment Unit: A 2-bedroom, 1-bath garden unit offers immediate rental income potential, finished to the same high standard as the owner's unit - quartz countertops, custom cabinetry, and an induction range. Whether you're offsetting your mortgage or building a rental portfolio, this unit delivers flexibility from day one. Solar-Powered & All-Electric Efficiency: Every system in this home runs on electricity, powered by on-site solar - meaning lower utility costs, a smaller carbon footprint, and a home built for the future of energy. High-performance construction is evident throughout, with triple-pane windows, Broan ERVs for continuous fresh air, and staggered stud framing with continuous spray foam insulation for a tight, comfortable building envelope year-round. Outdoor Space & Parking: A completely fenced, extra-large lot offers privacy and outdoor space rarely available with new construction in the city. The future-proof, EV-ready 2-car garage means your electric vehicle charging needs are already covered. The North Lawndale Opportunity: Positioned in one of Chicago's most dynamic West Side neighborhoods, this property puts owners close to Douglas Park, growing neighborhood investment, and easy access to downtown - all while offering the rare combination of single-family living and rental income in one address. All Electric. All New. All Yours.

3256 W Douglas Boulevard, Chicago

$750,000
6 Beds 3 Baths 12733894 MLS ACTIVE Status
Legal 2-unit frame multi-family building on a 3,125 sq ft lot with a nice backyard and 2-car garage. Attractive greyish exterior with roof extension/dormer. Substantially rehabbed in 2020 with new mechanicals (furnaces and water heaters in both units from 2020), updated appliances, and targeted renovations. Unfinished lower-level houses electrical panels plus Unit 1's furnace and water heater. Separate entrances. Unit 1 (first floor): 3 bed / 1 bath, approximately 1,200 sq ft. Fully rebuilt to the studs with a complete remodel. In-unit washer/dryer toward the rear near the third bedroom and back exit to the porch/staircase. Quiet mechanicals located downstairs. Unit 2 (duplex-up): 3 bed / 2 bath. approximately 2400 sq ft. Own entrance via staircase; and shortcut staircase entrance to upper level. Main level features a large living room with tall windows and strong natural light overlooking the avenue, laundry room, bedroom with normal closet space, kitchen with newer white Shaker upper cabinets / dark brown lower cabinets and 2020 appliances, generous dining room surrounded by windows, and rear exit. Upper level with secondary access via rear staircase includes a craft station with cabinetry and sink, access to a private wooden deck overlooking the property, second bedroom with normal closet space, full bath with vintage green tile and Hollywood-style circular bulbs (partial upgrades only during rehab-not fully gutted), and a very large master bedroom with vanity fireplace, nice closet space, and closeted mechanicals (unit's furnace and water heater). This unit received targeted renovations- kitchen updates, and first-floor bath work; remaining areas fixed up. Ideal for owner-occupant (live in one, rent the other) or investor. Both units available for viewing. Unit 1: May 31st, 2027, lease, $1995 with tenant planning to move. Rent projections $2400. Unit 2: Freshly vacated, rent projections $3500. Location in the 60647 area near North Avenue offers access to neighborhood amenities.

1621 N Talman Avenue, Chicago

$1,247,500
7 Beds 4 Baths 12722849 MLS ACTIVE Status
SECOND CHANCE AT AN EXCEPTIONAL LINCOLN SQUARE PROPERTY! Back on the market after the previous buyers were unable to move forward. This beautifully maintained 2-unit property features a rare DUPLEX-UP + DUPLEX-DOWN configuration with 7 BEDROOMS, 4 FULL BATHS AND A 2-CAR GARAGE. The 4-bedroom duplex-up is NOW VACANT AND EASY TO SHOW, offering excellent upside potential for an owner-occupant or investor. Live in one unit and collect rent from the other, lease both DUPLEXES, or explore the conversion to a spectacular single-family home. Unit 1 is a spacious 3-bed/2-bath duplex-down with a renovated kitchen, stainless appliances, granite counters, island, updated baths and mudroom.The tenants for the DUPLEX-DOWN are currently finishing up a 2 year lease on 4/27, with large upside potential to significantly increase the monthly rent. Unit 2 is an expansive 4-bed/2-bath duplex-up with a renovated kitchen, breakfast island and separate dining area. Both units have IN-UNIT LAUNDRY. Enjoy a beautifully landscaped property, private gated backyard with custom pavers and a large entertaining/grilling area, plus a detached 2-CAR GARAGE. Fantastic location on a quiet, one-way, tree-lined street near Winnemac Park, restaurants, shopping, transportation and everything Lincoln Square has to offer including Lincoln Avenue. INCREASED RENT + VACANT DUPLEX-UP + PRIME LINCOLN SQUARE LOCATION. Easy to show - don't miss this opportunity!

4937 N Bell Avenue, Chicago

$799,000
6 Beds 4 Baths 12702247 MLS ACTIVE Status
Welcome to this absolutely stunning & unique 2-unit home nestled on a quiet tree-lined street in prime East Garfield Park, less than a block from the $42M newly announced Madison Street Athletic & Cultural Complex. Must see to really appreciate this a fully reimagined frame/brick home showcasing meticulous craftsmanship and high-end designer finishes throughout. Unlike in most multi-unit properties, the upstairs duplex lives like a sophisticated single-family residence with great entertaining space, high ceilings, formal dining, along with 4 bedrooms and 2.5 baths. The main upstairs unit features a spa-inspired primary bath suite that is nothing short of true luxury. The first floor offers a bright open-concept layout, anchored by a chef's kitchen with 36-inch range, hidden walk-in pantry, wine fridge, dramatic waterfall island, custom cabinetry, and premium SS appliances, including a second, separate beverage center. There are also custom built-in cabinets in the dining room, as well as crafted shelving & an electric fireplace wall with recessed TV in the Family room that all come together beautifully with the gleaming Amish-grade hardwood floors and custom lighting throughout that helps create a warm and cozy environment. Heading out from the kitchen is an amazing mudroom that leads straight out to the newly built metal/concrete raised back deck and cozy landscaped back yard that creates a refined space for entertaining or relaxing. The stamped and stained concrete in the back add to the experience. This home has been beautifully and thoughtfully renovated to enhance the character and charm while being completely updated to exceed today's standards. In addition to the upstairs luxury home, it also has an amazing garden unit that will generate more than enough income to cover property taxes, maintenance, utilities, insurance, and even some debt coverage on the loan. This garden 2 bed/1 bath unit is no exception to quality, and will make for an ideal rental, in-law suite, guest quarters, nanny suite, work space or there's potential to expand the upstairs unit to create an even larger single family home. The garden simplex has 2 bedrooms, 1 modern bath with a tub, a bright and airy living room, a separate dining area, a beautiful custom kitchen with new SS appliances and quartz counters, not to mention in-unit laundry hook-up and warm porcelain tile throughout. All of the mechanicals are new and include new copper water service, all new underground plumbing with backflow prevention valve, all new 400 Amp electric, each unit has separate energy efficient furnaces, A/C's and individual tankless hot water heaters. New rood, new gutters, new siding, spray insulation for added efficiency, all new energy efficient windows, and a new heated flat-roof garage that could be converted to a rooftop deck. There is simply too much to list.

2839 W Monroe Street, Chicago

$589,000
4 Beds 3 Baths 12724342 MLS ACTIVE Status
Your home should work harder for you. This brand-new construction Two Flat is perfect for first-time buyers and those seeking low-maintenance ownership with income, accessibility, affordability, or multigenerational living. Built by award-winning Greenline Homes, this high-performance, all-electric, two-unit building combines elegant design with cutting-edge building science. Every detail, from the premium Hardie Board exterior to the EV-ready garage and gated intercom security, is crafted for effortless, low-maintenance living. The primary unit on the second floor offers a condo-quality 2 Bedroom + 2 Bath layout The unit features a chef's kitchen with custom cabinetry, quartz countertops, and a premium Induction range. An expansive private balcony extends from the great room, offering a seamless indoor/outdoor living experience.The stunning grade-level accessible first-floor offers a easy to rent 2 Bedroom + 1 Bath Layout that interfaces well with the private rear yard. This unit provides a spacious retreat, perfect for multi-generational living or generating high-value rental income to enhance affordability. Each Greenline Home is appointed by a designer with tastemaker-grade finishes. Embrace custom cabinetry, designer quartz, and induction cooking in a home designed for the next 100 years, not the last. With triple-pane windows for ultimate thermal comfort and a fully paid-for solar PV system, enjoy near-zero utility costs without compromising on style. Your comfort and investment in this home will last for generations. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. Schedule your showing today to explore Chicago's best-priced new construction.

6553 S Rhodes Avenue, Chicago

$579,800
6 Beds 3 Baths 12719311 MLS ACTIVE Status
Welcome to 5702 S. Wabash Ave - where luxury, style, and opportunity meet. This stunning, brand-new two-unit building in 60637 ZIP Code is the definition of modern elegance. Every inch has been thoughtfully designed with high-end finishes, soaring ceilings, and impeccable craftsmanship from top to bottom-electrical, plumbing, HVAC, roof, windows, porch and flooring are all completely new, offering true peace of mind. The expansive first unit features a beautifully designed duplex layout with 2 spacious bedrooms and 1 bath on the main level, flowing into a lower level with an additional bedroom, a massive spa-like bathroom, and a comfortable living space-perfect for relaxation or extended living. Both units showcase sleek quartz countertops, custom cabinetry, and designer kitchens with oversized islands made for entertaining. Each unit offers generous living and dining areas, along with well-proportioned bedrooms that provide both comfort and versatility. The bathrooms are nothing short of stunning-you will absolutely fall in love. Perfect for an owner-occupant or investor, this property offers the ideal setup to live luxuriously while generating income. Location is everything, and this one delivers. Enjoy easy access to Interstate 90/94, public transportation including the Chicago Red Line, and nearby green spaces like Sherwood Park and Washington Park. You're also just minutes from University of Chicago, plus shopping, dining, and everyday conveniences along Garfield Boulevard. Outside, enjoy a brand-new porch, a spacious yard, and rare three-car tandem parking in the rear. The curb appeal alone sets this home apart, with a front presence that feels as grand as it is inviting. This is more than a property-it's a lifestyle, an investment, and a rare opportunity to own something truly unique. Come experience it for yourself

5702 S Wabash Avenue, Chicago

$589,000
3 Beds 3 Baths 12717920 MLS ACTIVE Status
Your home should work harder for you. This brand-new construction Two Flat is perfect for first-time buyers and those seeking low-maintenance ownership with income, accessibility, affordability, or multigenerational living. Built by award-winning Greenline Homes, this high-performance, all-electric, two-unit building combines elegant design with cutting-edge building science. Every detail, from the premium Hardie Board exterior to the EV-ready garage and gated intercom security, is crafted for effortless, low-maintenance living. The primary duplex unit offers a condo-quality 2 Bedroom + 2 Bath layout upstairs with a versatile duplex to the main-level bonus room, ideal for a high-end home office, a third bedroom, or home gym. The unit also features a chef's kitchen with custom cabinetry, quartz countertops, and a premium Induction range. The stunning grade-level accessible first-floor interfaces well with the private rear yard and extra-wide garage. Both the garage and main-level unit are ADA accessible. This unit provides a spacious retreat, perfect for multi-generational living or generating high-value rental income to enhance affordability. Each Greenline Home is appointed by a designer with tastemaker-grade finishes. Embrace custom cabinetry, designer quartz, and induction cooking in a home designed for the next 100 years, not the last. With triple-pane windows for ultimate thermal comfort and a fully paid-for solar PV system, enjoy near-zero utility costs without compromising on style. Your comfort and investment in this home will last for generations. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. Schedule your showing today to explore Chicago's best-priced new construction.

6852 S Langley Avenue, Chicago

$639,000
5 Beds 5 Baths 12715315 MLS PRICE CHANGE Status
Stunning New Construction 2-Unit in the Heart of Booming Humboldt Park! Owner-occupants may qualify for up to a $20,000 grant through the Cook County Land Bank program, making this an incredible opportunity to own a luxury home while generating rental income. The ground-floor 2-bed / 2-bath unit is currently rented for $1,900 per month, helping offset your mortgage from day one. Above, the spectacular duplex-up lives like a single-family home with an ideal blend of modern luxury, thoughtful design, and expansive living space. The main level of the duplex features a sun-filled open-concept layout perfect for entertaining, complete with a designer kitchen showcasing quartz countertops, high-end stainless steel appliances, custom finishes, and enhanced foam insulation for added comfort and efficiency. A half bathroom on the main level adds convenience for guests and everyday living. Upstairs, retreat to an oversized luxury primary suite featuring two massive walk-in closets and a spa-inspired bathroom with both a soaking tub and a separate glass shower. Two additional spacious bedrooms and another full bath complete the upper level. Both units offer luxury vinyl flooring, in-unit laundry, and garage parking. Whether you're an investor or an owner-occupant looking to build wealth while living in style, this is a rare opportunity in one of Chicago's fastest-growing neighborhoods. Opportunities like this are hard to find - a brand-new construction property that combines luxury living, rental income, and potential grant assistance all in one of the city's most exciting and rapidly appreciating areas.

544 N Lawndale Avenue, Chicago

$674,999
9 Beds 3 Baths 12713376 MLS RE-ACTIVATED Status
This brick multi-unit building in Albany Park is a rare house-hacker and investor opportunity, with 3 spacious 3-bedroom units, a fully finished lower level, and recent big-ticket upgrades already done. These large 3 bedroom units, each with a primary bedroom, formal dining, sunlit living room, and a bright sun room. Market rent runs approximately $2,300 to $2,600 per unit. Expansive finished lower level with its own kitchen and full bath, perfect for extended-family living, a private guest suite, or generous owner space. NEW building roof and NEW garage roof, so the major capital expenses are already handled. Detached garage plus an additional parking pad, opening the door to extra parking rental income. On-site coin-operated laundry for another stream of supplemental revenue. ADU upside: Zoned multi-unit residential, where Chicago's permanent Additional Dwelling Unit ordinance (effective April 2026) now permits ADUs by-right. Buyers may have a path to explore legalizing additional living space as a conforming ADU, adding a potential third income stream. Buyer to verify ADU eligibility and approvals with the City of Chicago Steps to the CTA Brown Line, Kedzie and Lawrence dining and shopping, Ronan Park, and the Chicago River trail, with fast access to downtown and the expressways. Albany Park is one of the city's most in-demand rental corridors, and tenants want to be here. Live in one unit, rent the others, and let parking and laundry pad your bottom line. Whether you are building generational wealth, buying your first investment, or growing a portfolio, this is the kind of Albany Park building that does not last. Schedule your private showing today.

4918 N Monticello Avenue, Chicago

$949,000
3 Beds 4 Baths 12711516 MLS ACTIVE Status
NEW PRICE. Rare turnkey opportunity for an operator or investor seeking a fully renovated, PPA-licensed venue with uncommitted VGT potential in a prime Chicago corridor - includes Real Estate, Business, and Assets. Unlike standard restaurant offerings, this 4,055 SF freestanding corner asset includes a rare Public Place of Amusement (PPA), Liquor, and Food license, enabling the owner to collect cover charges or donations for ticketed events, raffles, live music, comedy, and more - creating multiple high-margin revenue streams beyond traditional food and beverage. The VGT-ready game room is currently uncommitted to any gaming operator, giving a new owner full leverage to negotiate their own terminal operator agreement and signing incentives. The restaurant was fully gut-rehabbed in late 2024, offering a new dining & bar space that seats 95 and a brand-new fully equipped commercial kitchen featuring pizza ovens, extended range, stove, prep areas, a walk-in cooler, and much more. The property functions as a clean, SBA-compliant operating shell primed for immediate occupancy - a true plug-and-play asset priced to bypass construction and permitting delays, minimize capital requirements, and facilitate a seamless acquisition of all existing licenses and FF&E. Situated on a 0.16-acre lot, the property features a 3,125 SF main level, a dedicated +15-car parking lot with ample street parking, and a 930 SF 3-bedroom residential unit for additional income. The site offers prime frontage on Irving Park Road near Harlem Avenue and the Harlem-Irving Plaza (HIP), capturing high visibility from over 26,000 vehicles per day (VPD) within a densely populated residential corridor. Contact Listing Agent for showings and details.

7455 W Irving Park Road, Chicago

$750,000
5 Beds 5 Baths 12703877 MLS ACTIVE Status
***$20,000 Grant Available Through the Cook County Land Bank!*** Rare opportunity in the Historic Garden district of East Garfield! Welcome to 2832 W Wilcox, a truly one-of-a-kind property that offers the best of both worlds. A rare cross between a traditional 2 flat and a single family home. This legal 2-flat encompasses 3150 Square feet, a total 5-bedrooms, 4.1 bath spanning 3 levels of living space. You can't get better than a dual Primary Suite, dual HVAC, dual Laundry area, and dual Kitchen. Private side entry for each unit. Whether you are searching for a multi-generational living arrangement, an owner-occupied investment, or a flexible property with endless possibilities, this unique residence delivers. Nestled on a tree line street, this sought after East Garfield property is just minutes away from the United Center and the transformative 1901 redevelopment project. This distinctive home offers an adaptable floor plan that provides the privacy and comfort of a single-family residence. Upper level showcases a primary suite with pass thru dual walk-in closets, a spectacular primary bath with dual vanity, freestanding tub, and oversized separate shower. Enjoy two generous guest bedrooms, oversized guest bath with double vanity sinks and laundry center. The incredible English garden level offers 2 Bedrooms and 2 bath, full living room, full kitchen with quartz countertops and stainless appliances. Your opportunity awaits so schedule your private tour today.

2832 W Wilcox Street, Chicago

$725,000
6 Beds 4 Baths 12702733 MLS ACTIVE Status
Take a look at this beautiful, West Ridge jumbo brick legal 2-flat w/a non-conforming full 1-bedroom garden unit. First time on the market in 44 years! The first floor unit has been occupied by the owner for the last 44 years! It consists of 2 bedrooms plus a tandem room that is heated, has windows and a closet, and 1 full bathroom. Open-concept floor plan allows for the large, formal living room to flow right into the formal dining room. A large, remodeled eat-in kitchen w/stainless steel appliances completes the first floor. The second floor unit contains 3 bedrooms plus a tandem room and a full bathroom. It also features a formal living room and dining room, and a large eat-in kitchen. The basement has a separate laundry room with a 1/2 bath, and a separate utility and storage area. The non-conforming remodeled garden unit features 1 bedroom, 1 bathroom and an open concept floor plan that allows the kitchen to flow into the living/dining room combo. The garden unit has two access points, including a private front/side entrance. Enclosed back porch. 3-car brick garage. For peace of mind, both the building and garage roofs were replaced two years ago. Second floor tenants are month-to-month. This is great for an investor or to be occupied by the owner. This one surely won't last long, so don't hesitate and schedule your showing today! Neither the seller nor the agent represent the legality of the garden unit.

6718 N Campbell Avenue, Chicago

$1,500,000
6 Beds 2 Baths 12696771 MLS ACTIVE Status
Rare opportunity to own a unique mixed-use property offering exceptional income and redevelopment potential. Located in a prime Avondale location just east of the California/Elston intersection...this 75' x 120' triple lot has 75 feet of frontage along Belmont Avenue and contains a fully renovated all-brick 2-flat , a large brick carriage house/garage, and a private parking lot...The brick 2-flat was completely renovated in 2019 and features two spacious 3-bedroom, 1-bath apartments with large living rooms, bay windows, separate dining rooms, modern kitchens with granite countertops and SS appliances, updated bathrooms with walk-in showers, engineered wood flooring, in-unit laundry, central heat and AC, and private outdoor decks. A shared ground-level patio provides additional outdoor space. The full unfinished basement offers approximately 7.5-foot ceilings and provides excellent storage or future expansion potential...The approx. 1,800 SF all-brick carriage house/garage features impressive 16.5-foot ceilings and offers various possibilities under M1 zoning, including workshop, studio, storage, light industrial, showroom, or other creative commercial uses (buyer to verify permitted uses)....The expansive side parking lot (approximately 50' x 90') provides abundant parking or future development opportunities. An outstanding opportunity for investors seeking stable rental income or owner-users looking for a flexible property with significant upside in one of Chicago's most desirable neighborhoods.

2732 W Belmont Avenue, Chicago

$650,000
5 Beds 4 Baths 12685639 MLS ACTIVE Status
Value & Location: "Stunning Duplex with Dedicated Property Easement next to Kennicott Park!" Discover an incredible investment or house-hacking opportunity in Chicago's Historic Kenwood neighborhood. Priced to sell, this unique, townhouse-style two-unit building spans multi-level living space. Situated directly across from the scenic Kennicott Park and minutes from DuSable Lake Shore Drive, this property is perfectly configured for an owner-occupant looking to live comfortably while collecting premium rent, or for an investor seeking a high-demand multi-family asset. Additionally, the parcel features a legal property easement, providing guaranteed side yard buffer, private access, and flexibly usable outdoor space adding long-term functional value to the house. The Owner's Suite A massive, sun-drenched multi-level layout designed for comfortable everyday living. Main Level Entertaining: Open-concept living and dining areas feature high ceilings. Upper-Level Bedrooms: Two spacious, private bedrooms are tucked away upstairs, one bedroom on the ground level, including with its own bathroom in brand new rehabbed part. Garden level: living room, laundry room, utility room, bathroom, bedroom and office, with separate egress through public room from garden level. Park Views: Enjoy beautiful tree-lined views in directly north to local green park space, and rapid access to close-by Burnham Park via 43rd street bridge over LSD, just steps away. The Income Suite Smart Multi-Level Layout: Perfectly proportioned and maximizing space, making it highly attractive to premium renters. Flexible 1.5-Bedroom Design. Features a spacious primary bedroom with mantle piece plus a versatile half-bedroom, ideal for a home office, nursery, or creative studio. Hallway closet. Turnkey Rental: Equipped with a funcitonal kitchen, bright living area, and independent private entry to ensure total resident privacy. Unbeatable Kenwood Location: Next to Kennicott Park: Step right outside to enjoy the Kennicott Park Fieldhouse, community programs, fitness facilities, sports fields. Commuter's Dream: Enjoy rapid access to Downtown Chicago via DuSable Lake Shore Drive 39th or 47th street ramps, or use nearby 43rd street Dan Ryan expressway ramp. Public Transit Friendly: Located steps from convenient CTA bus routes and Metra Electric District 47th street station ensures a seamless daily commute. Building & Exterior Features Property Easement: Benefit from a built-in property easement that ensures easy accessibility and use for outdoor activities. This easement is a source of natural light on the west side of the house. Separate metered electric utilities ensures stress-free management, shared radiator system and gas ensures efficiency. Townhouse Structure: Vertical layout ensures no neighbors are living above or below your primary living areas.

1132 E 44Th Street, Chicago

$599,000
8 Beds 3 Baths 12682270 MLS ACTIVE Status
Exceptional opportunity to own a solid brick legal 2-flat with a finished lower-level unit in the highly desirable Brighton Park neighborhood! This well-maintained property offers three spacious levels of living space, each with separate gas and electric utilities, making it ideal for owner-occupants or investors. The first-floor unit features 3 bedrooms with ceiling fans, a bright living room, formal dining room, kitchen, full bath, 9-foot ceilings, recessed lighting, beautiful hardwood floors, and the convenience of in-unit laundry. The second-floor unit offers a similar spacious layout with 3 bedrooms, living room, dining room, kitchen, and full bath. The finished lower level provides additional living space with 2 bedrooms, a large living area, kitchen, and full bathroom. Major updates include newer plumbing and electrical on the first floor and lower level, updated electrical panels, new rear porch siding, new windows on the second-floor porch, vinyl replacement windows, front wrought iron fence, roof approximately 9 years old, tuckpointing completed about 6 years ago, and three hot water tanks (one newly installed in 2026, others approximately 3-6 years old). Each unit has its own furnace, and both the first and second-floor units feature central air conditioning (approximately 10 and 4 years old). Conveniently located within walking distance to McKinley Park and just minutes from I-55, shopping, restaurants, Midway Airport, and downtown Chicago. Owner-occupants may also qualify for the City of Chicago grant programs for eligible buyers. A fantastic opportunity to build wealth through owner-occupancy or expand your investment portfolio!

2434 W Pershing Road, Chicago

$669,000
7 Beds 3 Baths 12679025 MLS ACTIVE Status
Vintage Rosedale Park 2-Flat in Highly Desirable Norwood Park East! Step into timeless Chicago charm with this extra-large vintage 2-flat located in the far North West side. Rich in character and architectural detail, this well-maintained property offers spacious living areas, classic craftsmanship, and incredible versatility for both owner-occupants and investors. Each unit features sun-filled living rooms with original built-in bookcases and decorative fireplaces, formal dining rooms perfect for entertaining, eat-in kitchens with walk-in pantries, and three bedrooms (including a tandem third bedroom). Vintage archways, French doors, beautiful unpainted cove moldings, original trim work, and generous closet space showcase the home's historic appeal. Hardwood floors are believed to be preserved beneath the carpeting. The full semi-finished basement adds valuable living and storage space with a family room, additional bathroom, utility area, two sets of washers and dryers, and ample storage. Enclosed rear porches provide additional usable space, while the detached 2-car garage offers convenient parking. Major updates include a new roof (2024) and two new hot water tanks recently installed (2026), Windows and tuckpointing done in 8 years ago, providing peace of mind for years to come. Ideally situated within walking distance to schools, parks, CTA transportation, the Blue Line, Metra station, and offering easy access to the Kennedy Expressway and O'Hare Airport, this is a rare opportunity to own a classic Chicago 2-flat in a premier location. Whether you're looking for an investment property, multi-generational living, or a chance to own a piece of Chicago history, this Norwood Park East gem is not to be missed!

5922 N Melvina Avenue, Chicago

$575,000
7 Beds 2 Baths 12676518 MLS ACTIVE Status
Welcome to a spacious vintage home with all the amenities of luxurious city living. Located In up and coming historic Bronzeville, just south of downtown, this gem boasts two generous units with high ceilings and spacious living and dining areas. This exceptional property blends classic Chicago character with all the modern comforts of a home. Whether you seek a strong investment opportunity or a spacious owner-occupied home with additional income opportunity, this well-maintained building offers flexibility, income potential, and ample room to grow. Classic 2-unit frame featuring in the first floor 3 br and 1 bath, in the second unit 4 br 1 bath. Both units feature updated kitchens, spacious living areas with sunny rooms and gleaming hardwood floors. The charm of this property is the thoughtful layout of its spacious units that feature both the very efficient layout of a 3- and a 4-bedroom/1Br unit together with large open living and dining areas, including a fireplace on the second floor. One unit is vacant, the other will be vacant later this summer. Ideal opportunity for an owner-occupant to enjoy the Fall season in this sought-after neighborhood. The additional unit offers immediate cash flow. Steps away from local transit of the green line stop, close to parks and neighborhood cafes and centrally located to access the expressway. Additional highlights include access to a large garden, two paved parking spaces in the back, shiny hardwood floors, custom cabinetry, central A/C in both units, separate washer/dryer hookups in the shared basement. The potential of this property lies in its unfinished basement and a spacious unfinished attic. This duplex awaits your ideas to enjoy it as resident owner or to turn it into a more efficient income property. Come and discover the potential of this Bronzeville gem.

4339 S Indiana 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

$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

$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

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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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