View All Jefferson Park Chicago IL 2-Flats Listings

$599,900
5 Beds ⋅ 3 Baths ⋅ 12755079 MLS ⋅ NEW Status
JEFFERSON PARK GEM WITH A BACKYARD RETREAT LIKE NO OTHER! Meticulously maintained and exceptionally inviting, this charming 2 flat, within walking distance to Jefferson Park station, offers spacious living and dining rooms, beautiful hardwood floors, a newer kitchen, a 2nd floor rental unit and a fully finished basement ideal for extended family, guests, recreation, or additional living space. But the true heart of this home is the extraordinary two-level rear deck. Directly connected to the house and accessible from both the first and second levels, this expansive outdoor living space is an entertainer's dream. A covered gazebo, mature grapevines, warm wood decking, and a built-in hot tub create a private backyard oasis that feels more like a destination than an ordinary city backyard. It's the perfect setting for summer gatherings, quiet evenings, morning coffee, or relaxing in the hot tub surrounded by greenery. The oversized, fully fenced yard provides exceptional privacy and additional space for entertaining, gardening, or enjoying the outdoors. This is more than a very nice Jefferson Park home-it is a home with a truly special outdoor lifestyle.

5128 W Ainslie Street, Chicago
$655,000
4 Beds ⋅ 2 Baths ⋅ 12751659 MLS ⋅ NEW Status
EXCEPTIONAL 2-FLAT | UPDATED UNITS | FLEXIBLE LIVING | INCOME POTENTIAL Beautifully maintained and thoughtfully updated, this versatile 2-flat offers an excellent opportunity for an owner-occupant, multi-generational household, or investor. Situated on a quiet residential street, the property features two, 2-bedroom, 1-bathroom units, each with updated kitchens, modern fixtures, comfortable living spaces, and the convenience of in-unit laundry. The enclosed rear stairwell leads to a well-maintained backyard, providing an outdoor space for entertaining, relaxing, gardening, or enjoying the outdoors. The basement offers additional flexibility with an in-law-style living area that can be used for extended family, guests, a home office, or potentially additional rental use, subject to applicable zoning and municipal requirements. Conveniently located near bus transportation with connections toward the Blue Line and close to a forest preserve offering walking trails, green space, and outdoor recreation. Whether you're looking to live in one unit and rent the other, accommodate extended family, or add a versatile property to your investment portfolio, this 2-flat offers updated living spaces, separate laundry, outdoor space, and multiple possibilities. A well-maintained multi-unit property with the flexibility today's buyers are looking for. Schedule your showing today!

5631 N Parkside Avenue, Chicago
$599,000
6 Beds ⋅ 3 Baths ⋅ 12746363 MLS ⋅ ACTIVE Status
Excellent opportunity to own this well-maintained brick 2-flat with a non-conforming 3rd unit in the basement. All 3 units have 2 bedrooms & 1 bath! This property offers spacious layouts, quality updates, & excellent income potential! Special unit feature include: Hardwood floors & a spacious deck overlooking the yard on the 1st floor & hardwood floors, a walk-in pantry, and an enclosed porch on the 2nd floor. Additionally there are thermopane windows throughout, a nice fully fenced yard, and a large 2 & 1/2-car garage with room for lawn equipment & a workbench. Front hallway freshly painted! Entire 1st floor and basement apartments painted last summer. Major improvements include a roof replacement in 2019 and most mechanicals recently replaced. Both hot water heaters in 2022 & 2025; 1st-floor furnace in 2022; & 1st-floor A/C in 2018. All this situated on an oversized 37' x 125' lot! Prussing School K-8 is just down the block! Lovely Neighborhood Location!

5839 W Eastwood Avenue, Chicago
$535,000
4 Beds ⋅ 2 Baths ⋅ 12733038 MLS ⋅ CONTINGENT Status
Welcome to 5302 N Luna Ave, a well-maintained two-flat located on a quiet, tree-lined street in highly desirable Jefferson Park. This versatile property is an excellent opportunity for an owner occupant looking to offset their mortgage with rental income or an investor seeking a solid multifamily addition to their portfolio. Both units offer comfortable layouts with beautiful hardwood floors, stainless-steel appliances, spacious kitchens, and updated bathrooms. Each unit features its own furnace and central air system, providing separate mechanicals and added convenience. The property also features separate water heaters, upgraded electrical panels, newer windows, roof, and multiple exterior decks. The full basement provides additional storage and utility space and includes separate laundry areas with two washers and two dryers, along with dedicated storage for each unit. Outside, enjoy a fenced-in yard and an oversized detached 2+ car garage-an excellent feature for additional parking, storage, or workspace. Situated on a 30 x 125 lot, the property offers plenty of outdoor space while maintaining a convenient urban location. Ideal location for city workers. Located near schools, shopping, dining, public transportation, major roadways, and the expressway, this property combines neighborhood charm with everyday convenience. Whether you're looking to live in one unit and rent the other or add a turnkey multifamily property to your investment portfolio, 5302 N Luna Ave is an opportunity you won't want to miss.

5302 N Luna Avenue, Chicago
$525,000
4 Beds ⋅ 3 Baths ⋅ 12743877 MLS ⋅ CONTINGENT Status
Nestled on the corner of a quiet, tree-canopied street, this sturdy 2-flat sits on an oversized lot, 39' by 129'. Each unit has hardwood floors throughout and consists of 5 rooms with 2 bedrooms, one bathroom, eat-in kitchen, living room with dining area and an enclosed back sunroom. Each unit also has separate hot water baseboard heat with newer furnaces (2022) and electrical panels. Located at the intersection of the Jefferson Park and Forest Glen neighborhoods, you are blocks away from the bus, Metra, Kennedy expressway, Mariano's, and beautiful Forest Preserves. Relaxing at home, you have two sunrooms and a cozy backyard at your disposal. Whether you're looking for an investment property with two quality units, a home for a growing family that features functional garden level living space, or a blank canvas for an ambitious renovation, come take a look and envision the possibilities.

5214 N Leamington 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
$790,000
8 Beds ⋅ 5 Baths ⋅ 12740081 MLS ⋅ ACTIVE Status
Amazing investment opportunty to own an updated legal 2-flat with a finished English Garden Unit with HIGH ceilings in Jefferson Park. This property offers generous living space, strong rental income, and excellent flexibility for an investor, owner-occupant, or multi-generational household. Both Unit 1 and Unit 2 feature 3 bedrooms and 1.5 bathrooms with thoughtfully redesigned floor plans that provide larger bedrooms than typically found in vintage Chicago buildings. Each unit offers bright living spaces, recessed lighting, updated kitchens with quartz countertops, stainless steel appliances, and ample cabinetry, plus one full bathroom and a convenient powder room. Unit 1 is currently leased at $2,650 per month, including electricity, gas/heat, water, trash removal, landscaping, and one garage parking space. Unit 2 is currently leased at $2,400 per month, including electricity and water. Together, the two legal units currently generate $5,050 in monthly rental revenue, or $60,600 annually. The finished basement is currently vacant but can provide additional flexible living space with 2 bedrooms and 1 full bathroom and an estimated rental potential of approximately $2,300 per month (MLS Comparable#: 12616160), subject to applicable laws, zoning, approvals, and permitted use. If legally approved for rental use, the property's potential combined gross income could reach approximately $7,250 per month or $87,000 annually. Additional features include an oversized deck above the garage, shared outdoor space, rear decks, and coin-operated washer and dryer, providing added convenience and potential supplemental income. Conveniently located near shopping, dining, transportation, parks, and neighborhood amenities, this is a versatile income-producing property with updated interiors, spacious layouts, and excellent long-term potential. Schedule your private showing today and explore everything this unique Chicago 2-flat has to offer.

5759 N Elston Avenue, Chicago
$579,000
4 Beds ⋅ 3 Baths ⋅ 12739570 MLS ⋅ ACTIVE Status
Beautiful, Legal 2 Flat with in-law arrangement in the heart of Jefferson Park. Excellent building includes top floor unit 2 Bed 1 Bath. First floor unit 2 Bed 1 Bath and in-law down for an additional Bed and Bath. Bright open units each equipped with private rear porches. Pictures only reflect second floor unit but first floor is even bigger and more updated. Long time owner, solid and well maintained building. Excellent locations, located on a quiet street close to restaurants, shopping, parks, schools, train and highway! This home has it all! Don't miss out! HURRY!!

4923 N Mason Avenue, Chicago
$599,900
6 Beds ⋅ 4 Baths ⋅ 12736543 MLS ⋅ CONTINGENT Status
MULTIPLE OFFERS. Located in Chicago's Portage Park neighborhood just south of Lawrence Avenue, this brick two-flat offers a solid investment or owner-occupant opportunity. Unit #1 spans the main level with 3 bedrooms and 1.5 baths, while Unit #2 occupies the second floor with 3 bedrooms and 1.5 baths of its own. A full, partially finished basement adds valuable extra space for storage and a detached 2-car garage round out the practical features. The brick exterior offers durability and classic two-flat character. Just steps from the Jefferson Park Transit Center - with CTA Blue Line, Metra, and bus access - and close to the neighborhood's shops, restaurants, and everyday conveniences along Lawrence Avenue, this property offers strong appeal for tenants and owners alike.

4552 N Lockwood Avenue, Chicago
$574,900
5 Beds ⋅ 3 Baths ⋅ 12736554 MLS ⋅ CONTINGENT Status
Location, Location, Location! Beautiful legal 2 flat in exceptional area. Situated on a prime corner lot in the highly desirable Jefferson Park/Forest Glen neighborhood, this meticulously maintained 2 flat features a first floor that offers a beautifully updated kitchen with granite countertops, stainless steel appliances, hardwood floors, and recessed lighting throughout the living room, dining room and sunroom, two spacious bedrooms, generous closet space, and full ceramic-tiled bath complete the first floor. The well cared for second floor features a living room, dining room, kitchen, two bedrooms and a full bath. The finished basement features a one bedroom suite complete with its own kitchen, full bath, and combined living and dining area, providing even more flexibility for multigenerational living. Conveniently located just minutes from the Metra, CTA blue line, Kennedy and Edens Expressways, and only one block from Mariano's and the secretary of State office. Broker or seller do not represent the legality of the basement in law suite.

5364 N Latrobe Avenue, Chicago
$465,000
4 Beds ⋅ 3 Baths ⋅ 12720915 MLS ⋅ CONTINGENT Status
Fantastic investment opportunity in Chicago! This 2-flat offers strong income potential with two legal units, each featuring 2 bedrooms and 1 bath, along with hardwood floors throughout. Ideal for investors. The property also includes a nonconforming basement unit, offering additional flexibility and potential for extended living or storage. A detached garage provides an added income stream, currently rented to a non-resident tenant. Conveniently located with easy access to local amenities, transportation, and more, this property is a smart addition to any portfolio. Don't miss this versatile, income-producing opportunity! Being sold AS-IS.

5212 N Ludlam Avenue, Chicago
$515,000
4 Beds ⋅ 2 Baths ⋅ 12698253 MLS ⋅ CLOSED Status
Situated on an extra wide lot in a premier location of Jefferson Park, this turnkey 2 flat presents an extraordinary opportunity for investors, multi-generational living, or house hackers - live in one unit and generate income leasing the other unit! Both bright and airy apartments feature 2 bedrooms with walk-in closets, 1 bath, tall ceilings, formal living and dining rooms, charming breakfast nooks, and a private 1st floor deck. Enjoy total peace of mind with key recent updates, including newer furnaces (2024), a brand new 2nd floor water heater (2026), and a modernized 2nd floor kitchen with updated cabinets, counter top, backsplash and faucet (2023). An enclosed rear staircase connects both levels to a massive unfinished basement and attic, offering value add potential for a duplex-up expansion or a single family conversion. Outside, a fully fenced landscaped yard leads to a 2 car garage offering additional storage or rental potential. Ideally positioned near Beaubien Elementary district, the Blue Line, Metra stations, bus routes, I-90/94, multiple forest preserves, many grocery stores, and neighborhood favorites like Gale Street Inn and Westons Coffee & Tap Co., this versatile property delivers unbeatable convenience, flexible living options, and immediate income potential!

4950 W Gunnison Street, Chicago
$575,000
5 Beds ⋅ 3 Baths ⋅ 12711245 MLS ⋅ CLOSED Status
Longtime owner offers this classic checkerboard two flat in super desirable Jefferson Park! Main floor unit features 3 beds and 1 full bath with large living room with crown molding, formal dining room with original woodwork and coved moldings throughout with nearly 9 ft ceilings (hardwood flooring under carpet)! Lots of windows (all 4 sides) and natural sunlight! 3 nicely sized beds, 1 full bath plus kitchen with large walk in pantry! 2nd floor unit features 2 beds and 1 full bath with with large living room, formal dining room plus large oversized kitchen with all appliances and pantry! Large back porch too! Full basement with 1/2 bath plus laundry room! Exterior features large patio overlooking well maintaned pine tree and garden area! 2 car detached garage! Great location...just steps to the blue line, minutes to the expressway and 10 minutes to the airport! Immediate possession if needed. Roof @ 10 yrs old and refurbished front stoop. Priced under recent appraisal...sold in as is condition! Opportunity is knocking!!

4933 W Ainslie Street, Chicago
$389,000
3 Beds ⋅ 2 Baths ⋅ 12715449 MLS ⋅ CONTINGENT Status
Clean, move-in ready 2-flat in the highly desirable Jefferson Park Pocket. Property features two units connected by an interior staircase and separated by a door, allowing flexible use as two separate units or one larger living space. Over the years, it has functioned both ways, making it ideal for an owner-occupant, investor, extended family, or multi-generational living. Main living areas are ready to enjoy, while the unfinished basement needs TLC and provides valuable space for storage, utilities, workshop use, or future ideas. Located near parks, transportation, shopping, restaurants, and neighborhood conveniences, with easy access to the Blue Line, Metra, I-90, and I-94. Adjacent curb-cut driveway lot at 4844 W. Gunnison is also available for sale and includes a 2-car garage with party door, creating a unique opportunity to purchase one or both properties. Property is being sold as-is.

4846 W Gunnison Street, Chicago
$829,900
8 Beds ⋅ 5 Baths ⋅ 12705609 MLS ⋅ ACTIVE Status
BEAUTIFULLY MAINTAINED BRICK 2-FLAT WITH A GARDEN APARTMENT IN THE MOST DESIRABLE NORWOOD PARK LOCATION BETTER THAN NEW, LESS 40 YEARS OLD. GREAT OPPORTUNITY FOR INVESTORS OR MULTI-FAMILY LIVING. JUST MINUTES AWAY FROM TOP-RATED SCHOOLS. FARNSWORTH ELEMENTARY SCHOOL AND TAFT HIGH SCHOOL. EACH OF THE 2 UNITS FEATURE 3 BEDROOMS AND 2 BATHS. LARGE KITCHEN WITH A DINETTE AREA. All SEPERATE UTILITIES. NEWER WINDOWS. 2.5 BRICK GARAGE. GARDEN APARTMENT WITH 2 ENTRANCES, HIGH CEILINGS, 2 BEDROOMS, 1 BATH HAS BEEN COMPLETELY REMODELED IN 2026. FRESHLY PAINTED. BEAUTIFUL KITCHEN WITH 42" WHITE CABINETS, GRANITE COUNTERTOPS, NEW FLOOR AND NEW RECENT LIGHTING. THE FIRST FLOOR APARTMENT IS CURRENTLY VACANT. THE ESTIMATED RENTAL POTENTIAL IS $2,600 FOR THE 1ST FLOOR. 2ND FLOOR APARTMENT ALSO WITH ESTIMATED RENTAL POTENTIAL OF $2,600. HAS LEASE THAT ENDS ON APRIL 2027. COIN-OPERATED LAUNDRY LOCATED IN THE BASEMENT. THE PROPERTY IS WITHIN WALKING DISTANCE TO JEFFERSON PARK TRANSIT-CENTER PROVIDING ACCESS TO CTA BLUE LINE, METRA AND AMTRAK. CLOSE TO KENNEDY EXPRESS AND EDEN EXPRESSWAY. CLOSE TO DOWNTOWN CHICAGO AND O'HARE AIRPORT.

5789 N Elston Avenue, Chicago
$500,000
5 Beds ⋅ 3 Baths ⋅ 12693558 MLS ⋅ ACTIVE Status
This legal 2-flat with a non-conforming garden unit sits on a generous 37-foot-wide lot with garage parking in one of Chicago's most in-demand Northwest Side neighborhoods. Portage Park delivers everything income-focused buyers look for: easy access to CTA bus and nearby Metra service, walkable proximity to grocery stores and everyday retail, and several neighborhood parks within blocks - the kind of location that keeps rental demand steady and turnover low. The investment case is compelling: strong in-place cash flow with a clear, well-supported path to 7% cap rate. Numbers are available upon request for serious inquiries. Whether you're expanding a multi-family portfolio or acquiring your first Chicago 2-flat, this is a rare combination of solid bones, prime location, and real upside. Schedule your showing today.

5730 W Windsor Avenue, Chicago
$630,000
5 Beds ⋅ 3 Baths ⋅ 12676092 MLS ⋅ CLOSED Status
Fantastic investment opportunity on a quite tree lined street of Jefferson Park. Legal 3 flat perfect for an investor or live in owner looking to invest in themselves. Get the best of both worlds with a wonderful mix of vintage charm and modern conveniences. Kitchens and baths have been remodeled a while ago but very nice. Two 2-bedroom 1 bath units plus a large 4 room one bedroom on top floor. Enclosed back porches and lots of extra storage. All units have separate furnaces. Located in a quiet little neighborhood of Jefferson Park near Beaubien School and perfectly situated with easy commuter access to I-90 off Lawrence or hop on the Blue Line or Metra train just a couple blocks away. Still, plenty of opportunity to expand... additional potential square footage in the full high basement. Brand new 2 car garage and a nice, fenced yard. Rents $1900. 1st floor, $1800. 2nd floor, $1550. 3rd floor and $250 for garage with a total of $5500. monthly or $66,000 yearly gross less expenses of $18522. equals a net income of $47128. A 7% return on a cash-on-cash investment. Property in good condition and being sold "as is'". Any questions, offers or concerns contact Norbert Mika. See agent remarks.

5008 W Strong Street, Chicago
$679,000
4 Beds ⋅ 2 Baths ⋅ 12672019 MLS ⋅ CLOSED Status
Solid brick two-flat with a non-conforming basement apartment located on a beautiful tree-lined street in sought-after Jefferson Park. The first-floor unit features hardwood floors, 2 bedrooms, 1 bath, spacious living and dining rooms, & a fully applianced kitchen with sliding glass doors leading to a large rear deck. An in-unit washer and dryer add convenience. The second-floor unit offers hardwood floors throughout, a bright living room, dining room, kitchen, and full bath. The non-conforming basement apartment includes 2 bedrooms, a kitchen, and living room, providing additional flexibility and potential income opportunities. Many newer appliances throughout the property. 2 brand new hot water tanks. Additional lwasher and dryer are located in the common basement area. Outside, enjoy a spacious fenced yard & storage shed. A 2-car garage, and 2 additional parking pads add additional income opportunities. All 3 units currently rented! Conveniently located near transportation, shopping, dining, parks, and everything Jefferson Park has to offer. Great investment opportunity! Sold AS IS. All offers require Mortgage Pre-Approval Letter. Cash Buyer-VERIFIED Proof of Funds No Love letters or Escalation Clauses Seller/Broker makes no representation of legality of bsmt apartment.

5038 N Mango Avenue, Chicago
$570,000
5 Beds ⋅ 4 Baths ⋅ 12667295 MLS ⋅ CLOSED Status
Exceptional investment opportunity on the border of Jefferson/Portage Park! This beautifully maintained and updated brick 2-flat with an additional finished garden apartment offers incredible flexibility for investors and owner-occupants alike. The spacious first-floor unit features 2 bedrooms plus a versatile den that can easily serve as a third bedroom or home office, a large sun-filled living room, formal dining room, updated cabinet kitchen, and a beautifully maintained bath. The recently refinished second-floor unit offers a bright and inviting layout with a large living room, formal dining room, updated kitchen, spacious bedroom, additional den with potential for a second bedroom, gleaming hardwood floors, and a stylish tiled bath with a whirlpool tub. The finished garden apartment provides additional living space with its own kitchen and bathroom, making it ideal for extended family or additional income potential (buyer to verify legal use). Outside, enjoy a lovely backyard, a huge garage with additional rental income, and a well-cared-for property that has been lovingly maintained over the years. Ideally located near Jefferson and Portage Parks, Jewel-Osco, restaurants, shopping, public transportation, the Blue Line, and the Kennedy Expressway, this property offers unbeatable convenience and easy access to downtown Chicago and O'Hare Airport. Whether you are looking to live in one unit while collecting rental income or expand your investment portfolio, this is a rare opportunity with strong existing income and upside.

4450 N Mango Avenue, Chicago
$475,000
3 Beds ⋅ 3 Baths ⋅ 12671001 MLS ⋅ CLOSED Status
Motivated Seller!!! Will consider all offers!!! Rare opportunity to own a well-maintained legal 2-flat in the highly sought-after Jefferson Park neighborhood. Ideally located near O'Hare Airport, major expressways, public transportation, and shopping, this property offers both convenience and long-term value. The building features a total of three bedrooms and three full bathrooms, with Unit 2 fully updated and showcasing modern finishes. A dedicated laundry room adds everyday convenience for tenants. The property also includes a solid brick two-car garage, offering excellent potential for additional rental income. Unit 2 is currently leased at $1200 per month through November 2026, providing immediate and stable cash flow. This is an excellent opportunity for a flipper's dream or owner-occupants seeking a prime location with strong upside. Additionally, the garden unit offers an additional bedroom, a full bathroom, a full kitchen, and two points of entry from the side and rear of the unit.

5552 N Major Avenue, Chicago
$695,000
6 Beds ⋅ 3 Baths ⋅ 12664676 MLS ⋅ CLOSED Status
Welcome to this meticulously maintained two-unit brick building in one of Chicago's most sought-after Northwest Side neighborhoods. Located on a peaceful cul-de-sac this home offers the perfect mix of comfort, convenience, and community. Both units are freshly painted, sparkling clean, and move-in ready, featuring beautiful hardwood floors throughout the first and second levels, central HVAC, and impressive updates. The first-floor kitchen boasts all-new countertops and backsplash, while both bathrooms have been renovated with heated floors. A brand-new roof was installed in the spring of 2024, hot water heaters were replaced in 2020, and the building is equipped with two Generac generators for reliable backup power. Additional highlights include a convenient enclosed back porch and custom built-ins for extra storage, a dedicated laundry room, ample storage space throughout the building, and a detached 2-car garage with extra cabinetry. The lower level offers excellent potential for an in-law suite or additional living space. Ideally situated for both owner-occupants and investors, this property is just minutes from the Jefferson Park Blue Line and Metra stations, easy access to the 90/94 expressway, HIP shopping center, Ridgemoor Country Club, and Wilbur Wright College. Excellent schools, parks, and neighborhood amenities are all right at your doorstep just a half-block from Dunham Park with its tennis courts, playgrounds, and recreation. This is a rare opportunity to own a well-cared-for, updated two-flat in a highly desirable Jefferson Park location. Don't miss out - schedule your showing today!

6122 W Leland Avenue, Chicago
$649,900
6 Beds ⋅ 2 Baths ⋅ 12657416 MLS ⋅ ACTIVE Status
Incredible Two-Flat in the Sought-After Jefferson Park Neighborhood! Don't miss this beautifully maintained and updated two-flat offering exceptional value for both investors and owner-occupants. Each spacious apartment features 3 bedrooms and 1 bathroom with an excellent, functional layout, abundant natural light, and beautifully refinished hardwood floors throughout. Both kitchens have been tastefully updated with white cabinetry, quartz countertops, and modern finishes, while the bathrooms have been stylishly renovated. Additional improvements include updated electrical panels, providing peace of mind for years to come. The property also offers a 2-car garage, private basement storage space for each unit, and separate washers and dryers for added convenience. Ideally located within walking distance to Indian Road Park and Hitch Elementary School, with easy access to shopping, dining, transportation, and everything Jefferson Park has to offer. A truly turnkey opportunity in one of Chicago's most desirable neighborhoods!

6029 N Austin Avenue, Chicago
$860,000
4 Beds ⋅ 2 Baths ⋅ 12642736 MLS ⋅ CLOSED Status
Highest and Best Offers due by May 26th at 11AM. This beautifully updated brick 2-flat with garden apartment shows pride of ownership everywhere you look! Sitting on a quiet tree-lined street close to the Jefferson Park Blue Line "L" stop and the Jefferson Park Metra Station as well and providing easy access to the expressways, downtown Chicago and the airport too, the location simply couldn't be better! This classic Chicago building sits on an extra-wide lot, offering ample yard space and a backyard patio as well as a new 2-car garage with party door. The property has been very well-maintained by its current owners and is in excellent shape. The 2nd floor owner's unit underwent a complete gut rehab and features a reconfigured floor plan with an amazing eat-in kitchen that's twice the size of typical kitchens, making it perfect for cooking and entertaining with tons of counter space, all stainless appliances and a gorgeous backsplash. It also features a beautiful new bathroom, 2 bedrooms including a huge primary bedroom with tree-top views, new windows and gas forced air heat with central air. 1st floor apartment is comprised of a large kitchen with 42" cabinetry, all stainless appliances, stone countertops and lots of storage and counter space, 2 BR's, an updated bathroom, separate dining room and huge living room. Garden apartment has been remodeled and has 2 bedrooms, a stunning bathroom and kitchen with all stainless appliances. Building improvements include new copper plumbing throughout, all new high-efficiency hot water heaters and HVAC systems, new garage, tear-off roof in 2013, and so many other thoughtful updates including mud-room areas in the back entrances with space to hang coats and sit down to put your shoes on and off. This property is in incredibly good condition and resides in a highly desired location close to transportation, restaurants, grocery stores, bars, entertainment, and the Six Corners as well.

5010 N Major Avenue, Chicago
$639,000
5 Beds ⋅ 3 Baths ⋅ 12637405 MLS ⋅ CLOSED Status
Welcome to Jefferson Park!! This charming Chicago classic corner 2 flat is well maintained and sits on an oversized lot. Perfect for investors or owner-occupants looking to generate rental income potential. Hardwood floors thru-out in both units and generous room sizes. Basement includes washer/dryer for each unit and separate storage spaces. Basement also gives additional living space plus two entrances. DON'T MISS THIS FANTASTIC OPPORTUNITY IN A PRIME LOCATION!!

5063 N Mango Avenue, Chicago
$525,000
3 Beds ⋅ 3 Baths ⋅ 12628249 MLS ⋅ CLOSED Status
Step into timeless elegance at 5042 W Winnemac Ave, a meticulously renovated all-brick 1929 Jefferson Park 2-flat that masterfully fuses historic charm with contemporary luxury. This property is a rare gem, offering two distinct units that cater to both multi-generational living and investment opportunities. Every detail has been thoughtfully designed to create a harmonious blend of historic character and modern convenience. First-Floor Duplex-Down (Unit 1) The main level and fully reimagined lower level of Unit 1 provide a sophisticated sanctuary with 2 bedrooms and 2 baths. The living room, featuring custom built-ins and freshly painted walls, exudes warmth and charm. Gleaming hardwood floors flow throughout the first floor, which also includes a versatile exercise room that can double as a private office. The gourmet kitchen is a chef's dream, complete with granite countertops, stainless steel appliances, and crisp white cabinetry that enhances the bright and airy feel of the space. The first-floor bathroom features a tub and shower combo, an updated vanity, and a modernized design. The fully renovated basement bathroom offers a luxurious glass-enclosed shower with subway tile and a sleek, contemporary aesthetic. The fully renovated lower level also boasts new laminate vinyl plank flooring and features a spacious family room and additional living space. Step outside to your private yard oasis, perfect for entertaining or relaxing, and enjoy the convenience of in-unit laundry. Attic Penthouse (Unit 2) Unit 2 is a light-filled 1-bedroom, 1-bath penthouse that combines charm and functionality. The eat-in kitchen features white cabinetry, butcher block countertops, and a stainless steel stove, creating a clean and modern aesthetic. While hardwood floors are found in several rooms, the hallway and kitchen feature alternate flooring for added practicality. The bathroom is a serene retreat, complete with a soaker tub, elegant millwork, and white cabinetry. The convenience of a washer/dryer combo enhances everyday living, making this unit as versatile as it is beautiful. Located in the prestigious Jefferson Park neighborhood, this property offers unparalleled convenience for commuters and city explorers alike. The home is just a short walk to the Jefferson Park Transit Center, providing access to the Blue Line train, Metra rail, and multiple bus routes, making travel to downtown Chicago and beyond a breeze. For drivers, the property is ideally situated near the Kennedy Expressway (I-90) and the Edens Expressway (I-94), offering quick and easy access to major highways. Whether you're heading to O'Hare International Airport, downtown Chicago, or the suburbs, this location ensures seamless connectivity. The 2-car garage is a standout feature, with its very tall ceilings that can easily accommodate a work van or truck, making it ideal for professionals or those with larger vehicles. The property is equipped with dual furnaces (2018/2005) and a 2015 water heater, ensuring comfort and efficiency year-round. This property is a true masterpiece, offering a unique opportunity to own a home that combines historic charm, modern updates, and exceptional functionality. Whether you're seeking a luxurious multi-generational home or a prime investment property, 5042 W Winnemac Ave delivers on every level. Don't miss your chance to experience the pinnacle of refined living, schedule your private showing today.

5042 W Winnemac Avenue, Chicago
$635,000
5 Beds ⋅ 3 Baths ⋅ 12546850 MLS ⋅ CLOSED Status
MOVE-IN READY | JEFFERSON PARK 2-FLAT | FANTASTIC INCOME OPPORTUNITY: Welcome to this beautifully maintained, English-style 2-flat on an extra-wide lot in highly sought-after Jefferson Park-just moments from the Blue Line, Metra, and 1-block from top-rated Beaubien School. With approximately 2,400 sq.ft. of finished living space, this home is ideal for live-in owners or savvy investors in a highly competitive rental market...offering immediate comfort and strong income potential.....FIRST FLOOR (2bd/1bth): Enjoy brand new luxury vinyl flooring and modern decor in a spacious living area that opens to a sunlit deck-perfect for outdoor entertainment. The backyard is a tranquil retreat, fully enclosed by a cedar privacy fence and landscaped with easy-care perennials for year-round enjoyment......SECOND FLOOR (2bd/1bth): Newly updated kitchen with contemporary cabinetry. Original hardwood floors. Cozy enclosed porch-great for relaxing with friends or as a create-your-own space. Ample closet/storage space and a bonus room ideal for an office or workspace.....FINISHED BASEMENT: Updated extra living space with bedroom, bath, etc. Perfect for extended family, guests, or flexible living options-----Additional Highlights: SS appliances throughout / Oversized 2.5-car garage (24x24) / 2024 HVAC / 2019 Roof and Siding / Significant storage on every level and w/in garage...and more! Don't miss this rare opportunity to own a well-maintained, income-generating property in one of Jefferson Park's most desirable locations. Move right in and start enjoying-or earning from-your new home today!

5034 W Argyle Street, Chicago
$620,000
7 Beds ⋅ 3 Baths ⋅ 12605083 MLS ⋅ CLOSED Status
**MULTIPLE OFFERS RECEIVED, HIGHEST AND BEST DUE MONDAY, APRIL 6TH AT 5:00 PM** Solid income-producing opportunity in a well-maintained 2-flat with additional garden unit (owner cannot confirm the legality of the garden unit), all fully occupied with tenants in place. Each unit features separate utilities, offering ease of management and strong rental potential. Property includes a private patio with a fenced yard and a 2-car detached garage. Conveniently located near expressways, public transportation, and local schools. Ideal for investors seeking immediate cash flow with tenants willing to continue current leases.

5054 N Lockwood Avenue, Chicago
$831,100
4 Beds ⋅ 2 Baths ⋅ 12560434 MLS ⋅ CLOSED Status
MULTIPLE OFFERS! HIGHEST AND BEST DUE 5PM ON 2/15/26. Do not miss an opportunity to purchase this beautifully renovated 2 flat on an oversized lot in Jefferson Park with a true duplex up owner's unit! Completely gut renovated with city permits in 2023, the 2nd floor unit is designed perfectly for a long term owner occupant who can enjoy offsetting their mortgage with additional rental income from the first floor unit. Virtually everything has been updated including copper plumbing, electrical with 200 amp service, furnaces, AC condensers, water heaters, appliances, kitchens, bathrooms, flooring, windows, and spray foam insulation. The 2 bed 1 bath owner's unit features an open floor plan with wide plank hardwood floors throughout, solid core doors, and abundant natural light. The modern Scandinavian inspired kitchen offers quartz countertops with a waterfall edge, huge island fitting 4 barstools, sleek cabinets with plenty of storage, upgraded stainless steel appliances, and an in-unit washer/dryer. Designer bathroom with step-in shower, a generous primary bedroom with walk-in closet, sizable second bedroom, and a bright rear sunroom perfect for a home office, gym, or cozy retreat. The top-floor living area impresses with soaring 11-foot vaulted ceilings, skylights, and newer plush carpeting. The first floor 2 bed 1 bath rental unit offers refinished hardwood floors, charming original doors and hardware, upgraded kitchen and bath, plus a rear sunroom. The unfinished basement provides excellent potential, with two separate entrances, a steel center support beam, and a practical 6'10" ceiling height-perfect for future expansion, storage, or added living space. The large fenced backyard presents a paver patio, solid deck, and 2 car garage with a party door. Prime Jefferson Park location that is steps away from multiple parks, the blue line, Metra, I90, Jewel Osco, and easy proximity to O'Hare airport.

4744 N Lotus Avenue, Chicago
$511,000
4 Beds ⋅ 3 Baths ⋅ 12554072 MLS ⋅ CLOSED Status
Ideal location to public transportion, expressways and airport. Great opportunity to own a two flat with loads of potential. The basic are good. Upgraded electric panels. 15 yr old boiler for radiant heat. Copper piping replaced. 50 gal hot water heater. Enclosed front porch and half finished basement with toilet and washer & dryer. Kitchens are eat in with the first floor extra sun room, Both unit's kitchens have walk in Pantrys. Vintage bathrooms. each unit has 2 bedrooms and the basement has its own access and toilet. 2 garage with alley access. Building is being sold as is, where is. firstGreat investment!

5207 N Ludlam Avenue, Chicago
$602,000
4 Beds ⋅ 3 Baths ⋅ 12521358 MLS ⋅ CLOSED Status
Classic Chicago brick two flat located in the heart of Jefferson Park! This building is in great condition with updated electrical. Unit 2 is currently rented for $1600 a month. Unit 1 is currently rented for $1500 a month. Both units have hardwood floors, a separate living room, separate dining room, kitchen, two full size bedrooms, one bathroom and an attached back porch. Each unit pays for their gas and electric. Included in the rent is water. The building has radiator heat and window units for the air conditioning. The basement is partially finished with a kitchen, full bathroom, storage and a washer & dryer. It is not a finished garden unit but can easily be one with some TLC. New roof and new gutters in 2018. The backyard includes a patio and a two-car garage. Excellent school district with Farnsworth for K-8 and Taft High School. Conveniently located near shops and restaurants. Plus, easy access to public transpiration, the blue line and the expressway. As Is Sale. Please and thank you.

5338 N Luna Avenue, Chicago
$625,000
9 Beds ⋅ 3 Baths ⋅ 12437405 MLS ⋅ CLOSED Status
Longtime family-owned and meticulously maintained, this rare extra-large 4,200 sq. ft. brick three-flat in Chicago's desirable Portage Park neighborhood offers a unique investment or owner-occupant opportunity. Each of the 3 spacious units features 3 bedrooms, a rare find in the area. Dry basement! 2 car garage! New boiler! Cash flow if owner occupancy as well as pure investment. Text Kelley to see this gem

5338 W Montrose Avenue, Chicago
$640,000
5 Beds ⋅ 3 Baths ⋅ 12526740 MLS ⋅ CLOSED Status
Highest and best offers due by Wednesday December 10th at 5PM. Well-maintained legal 2-flat with a non-conforming in-law apartment in the finished basement, ideally located in Jefferson Park. Both units feature spacious living and dining room combos with large eat-in kitchens. Unit 1 features 2 bedrooms, 1 bathroom, plus a den/bonus room off an enclosed porch, along with a nicely remodeled kitchen and bathroom. Unit 2 offers 2 bedrooms and 1 bathroom, with an enclosed porch currently used for storage and ready for updating. Coin-operated laundry conveniently located in the basement. The building is fully occupied with units on month-to-month basis. The brick 2 car garage is also rented. Solid brick construction with recent tuck-pointing completed within the last 3 years. Roof is approximately 10 years old. Both boilers are about 2 years old; one furnace is approx 1 year old, and the second furnace is older but in good working condition. Room sizes and room count are estimates, Buyer to verify. Excellent income-producing property in a desirable Jefferson Park location.

5555 N Mango Avenue, Chicago
$740,000
5 Beds ⋅ 3 Baths ⋅ 12501648 MLS ⋅ CLOSED Status
Discover this meticulously maintained 2-flat at 5774 N Elston Ave in vibrant Jefferson Park-a prime opportunity for investors or multi-family living! This move-in-ready property blends modern finishes with timeless Chicago charm. Each of the 2 units boasts open-concept layouts, gleaming hardwood floors, and gourmet kitchens with stainless steel appliances, quartz countertops, dishwashers, and breakfast bars. Stylish bathrooms feature designer fixtures, complemented by in-unit washer/dryers, central heat/AC, and tenant-paid utilities for effortless ownership. Relax in the private, landscaped backyard, perfect for unwinding or entertaining. Located steps from top-rated schools, parks, and transit (Blue Line & Metra), this property offers seamless access to downtown Chicago while enjoying a peaceful neighborhood vibe. Don't miss this turn-key gem at 5774 N Elston Ave-ideal for rental income or owner-occupancy. Schedule your tour today!

5774 N Elston Avenue, Chicago
$665,000
4 Beds ⋅ 3 Baths ⋅ 12496805 MLS ⋅ CLOSED Status
WELCOME TO THIS BEAUTIFULLY UPDATED BRICK 2 FLAT IN THE DESIRABLE JEFFERSON PARK. EACH UNIT WITH THE SAME LAYOUT FEATURES A SPACIOUS LIVING ROOM, DINING ROOM, 2 BEDROOMS, A DEN/OFFICE OR A THIRD BEDROOM AND AN ELEGANT BATHROOM. THE TOTAL REHAB IN 2023 INCLUDES: NEW ROOF (TEAR OFF) WITH ADDITIONAL INSULATION, NEW ELECTRIC SYSTEM WITH A NEW 200 AMP. SERVICE, NEW WINDOWS, DOORS, NEW CENTRAL HEATING AND AIR CONDITIONING UNITS, GORGEOUS KITCHENS WITH 42" CABINETS, QUARTZ COUNTERTOPS AND A STAINLESS STEEL APPLIANCES, STUNNING HARDWOOD FLOORS THROUGHOUT. TWO CAR GARAGE. EACH APARTMENT PAYS THEIR OWN HEAT, ELECTRIC AND GAS. THE FULL BASEMENT ALREADY HAS A VERY NICE BATHROOM AND THE REST IS WAITING FOR YOUR REMODELING IDEAS. GREAT LOCATION WITH A WALKING DISTANCE TO THE ELEMENTARY SCHOOL, CLOSE TO EXPRESSWAY, SHOPPING ETC. DON'T MISS THIS FANTASTIC INVESTMENT PROPERTY!

5510 N Luna Avenue, Chicago
$700,000
7 Beds ⋅ 5 Baths ⋅ 12491840 MLS ⋅ CLOSED Status
Fantastic opportunity in Jefferson Park! This well-maintained jumbo brick 2-flat is perfect for owner/occupants or investors. Each spacious unit offers 3 bedrooms, 2 ceramic title bathrooms, large living and dining rooms with carpeting over hardwood floors, and generous eat-in kitchens with ceramic title flooring--plus a brand new refrigerator in the first floor unit. First floor unit freshly painted. Hardwood floors throughout both units. The finished basement includes a recreation room with ceramic tile flooring, wet bar, electric fire place and a full bath, kitchen with new stove and bedroom. Ideal for extended family use. Utilities are separate (except water), and the property features a back porch, a fenced backyard accessed via the rear stairway and a detached 2.5-car garage. Located near bus stops, expressways, the Blue Line, schools, parks and shopping. Rental potential is strong for the area. Pre-qualified buyers only. Show and sell!

5705 W Higgins Avenue, Chicago
$727,500
5 Beds ⋅ 3 Baths ⋅ 12485436 MLS ⋅ CLOSED Status
Beautiful brick two-flat with additional In-law apartment in the basement with one bedroom, one bath. Both units offer, generous living and dining room, 2 bedrooms, den and one bath. Hardwood floors on each level. First floor apartment and in- law apartment completely redone with stainless steel appliances. All new windows thru out the building, except one, newer roof, siding on the back porch and detached two car garage. Great location, close to expressway, blue line and buses. Great opportunity for investors and owner occupant.

5626 N Central Avenue, Chicago
$570,000
5 Beds ⋅ 3 Baths ⋅ 12460326 MLS ⋅ CLOSED Status
Welcome to this beautifully maintained 2-flat with in-law suite, nestled on a quiet, tree lined street. This solid brick property has large 2 bedrooms / 1 bath units with heated bonus rooms which could be a terrific den or office. Additionally, there is central air through the entire building. The combined living/dining area can accommodate lots of large furniture pieces. The kitchens have plenty of room for breakfast tables. The lower level lays out as a massive in-law suite with a gorgeous newer bath, or it could make for a huge, lovely duplexed unit as the building has both front and rear stairs. It's an excellent, flexible floor plan. Unit 1 features newer appliances. The building also has a flood control system, 3 separate gas hot water boilers and free laundry in basement. The yard is beautiful and there's a large 2.5 car garage. Enjoy all that Jefferson Park has to offer such as fun restaurants, shopping, a Metra stop, a Blue Line stop taking passengers to both downtown and O'Hare, plus very easy highway access. Units are ready to rent right now, or with some cosmetic updates this could be a fabulous investment. The property is rock solid.

5132 N Mango Avenue, Chicago
$410,000
4 Beds ⋅ 3 Baths ⋅ 12457450 MLS ⋅ CLOSED Status
Frame 2 flat in need of total renovation in a great Jefferson Park location close to a school and a park. This property is on a large 50 foot lot features, 1st floor unit with 2 bedrooms, 2bath, dining room, and enclosed porch. 2nd floor features 2 bedrooms 1bath and an enclosed porch. Unfinished basement. 2.5 car garage. Sold in "as in" condition. Cash or construction loan only.

5222 W Winnemac Avenue, Chicago
$541,000
4 Beds ⋅ 2 Baths ⋅ 12455272 MLS ⋅ CLOSED Status
Desirable, air conditioned, brick 2-FLAT on attractive residential street with convenient location to Jefferson Park train and expressway access. Well maintained 2-FLAT features new roof in 2021, two new furnaces and one central air conditioning unit in 2016, new bathroom toilets and bathroom windows in 2023, new washers and dryer in 2024, new hot water heaters in 2023. Overhead sewer installed in 2007 (or 2008). Hardwood floors. Ample closet and storage space. Fenced backyard. 2 car garage (rented separately to 2nd floor tenant). Full, unfinished basement with doors to entry vestibule and backyard. Please note that rental prices are lower than current market value. This would be a great place to call home or to have as an investment property.

5107 N Mango Avenue, Chicago
$715,000
6 Beds ⋅ 4 Baths ⋅ 12390583 MLS ⋅ CLOSED Status
Unbelievable opportunity to live in sought-after Jefferson Park or expand your rental/investment portfolio with this impeccably maintained all-brick 2-flat featuring additional income-generating living space in the basement. Over $100K in recent improvements include a complete electrical service and distribution replacement ($37K, 2022) by ABC Electric with City of Chicago permits, new GFCIs, smoke/CO detectors, and Ring video doorbells; a fully renovated in-law suite ($40K) with new flooring, bathroom, kitchen, cabinets, and furnishings; and a new GAF roof ($10K) with Class A fire rating and 25-year limited warranty. Units 1 and 2 each offer 3 bedrooms, 1.5 baths, updated kitchens and baths (2019) with quartz counters and stainless steel appliances, hardwood floors under carpeting, fresh paint, and new exterior screen doors. The rented basement unit includes a full bath, bedroom, kitchen, living area, and laundry. Additional highlights include central air, generous outdoor space with a patio, 2-car garage, and parking pad. Located near O'Hare, I-90, I-94, CTA and Metra, this move-in-ready, income-producing property is a rare find you won't want to miss.

5534 N Central Avenue, Chicago
$578,000
4 Beds ⋅ 3 Baths ⋅ 12442985 MLS ⋅ CLOSED Status
Nice brick 2 flat building with a partially finished basement. Both the first and second floor have 2 bedrooms and full bath, eat in kitchen and living room. Each unit has its own furnace, central heat and central air. Enclosed porch and 2 car garage. Property is sold in "As-Is" condition.

5523 N Major Avenue, Chicago
$405,000
6 Beds ⋅ 2 Baths ⋅ 12441563 MLS ⋅ CLOSED Status
Buyer financing fell through! Back on the market and a great investment opportunity in prime Portage Park. Bring your development ideas to this 2 flat on a 35 ft wide lot. Create a great duplex down with the first floor unit and continue to produce income with the second floor. Or build your dream single family home. Both units have 3 bedrooms and 1 bath plus a bright and spacious living room, dining room and kitchen with walk-in pantry. Hardwood floors throughout and second floor has newer carpet. Outdoor spaces in both the front and back. Nice size yard with 2 car garage. Unfinished basement with washer and dryer. Prime location close to the Blue Line, Metra and buses. Easy access to 90/94 Selling As-Is

5037 W Sunnyside Avenue, Chicago
$718,000
5 Beds ⋅ 3 Baths ⋅ 12433150 MLS ⋅ CLOSED Status
****** NEWLY REMODELED!!!! ********* From TOP to BOTTOM * Multi-Generational 2-flat BRICK building, with DUPLEX Down/In Law space in a NEWLY BUILT OUT Finished Basement!!! ******** Sits on a Quiet, Tree-Lined Street in the Heart of Jefferson Park!!!! ****** Just steps from Public Transportation, Parks, Schools, and Shops!!! *********** Each Spacious Unit Features Hardwood Floors! ****** The NEWLY FINISHED BASEMENT Unit Could Possibly be a 3rd Standalone Unit due to it having a private entrance ****** Whether you're an Investor or Owner-Occupant, this property Offers the Chance to Live in one unit * while renting the other!!!! ******** Don't Miss this Rare Opportunity to Own a Property in one of Chicago's Most Accessible Neighborhoods!!!!!!! ********** ******* First floor unit Features 2 Bedrooms * 1 Bathroom * Plus an Additional Sun Room / Sitting room off of the 1st Bedroom!!!!! ******* along with a Kitchen * Open Space Dining / Living Room & Family Room ******* ******* Second floor unit Features 2 bedrooms * 1 Bathroom * Plus an Additional closet / Changing Room off of the 1st Bedroom!!!! ********** along with a Kitchen * Open Space Dinning / Living Room & Family Room ******* ******* Duplex down/ In- Law space features 1 Bedroom * 1 Bathroom * with a NEW Beautifully Appointed Stall Shower * A Huge Recreational Room * Large Kitchen Area with BRAND NEW SS Refrigerator * A Spacious NEW Laundry Room with Side-by-Side Washer & Dryer * and a Utility Room can be found on the Lower Level * Along with Plenty of Storage in the Basement!!!!!!! ************ ******* in ALL Units the Rooms Seamlessly Connect the Kitchens and Living / Dining Rooms, Creating a Cohesive Living Space!!!! *********** ****** Large Windows Provide Ample Natural Light!!! ******** ********* This WHOLE Property FEATURES All Brand NEW Vinyl Windows with NEW Window Treatments * New Electrical Panels * NEW Copper & PVC Plumbing * NEWLY Tuck-Pointed * NEW Water Heaters * New CENTRAL A/C & Furnaces for the Units * and ALL NEW SS Appliances ******** ***** WAIT...........There is MORE!!!!!!!!!!! ******** Did I say ALL NEW Exterior Trim & Doors * Newer Roof & Vinyl Siding * Motion lights illuminate the Back Staircases * and a NEWLY finished 2.5 Car Garage with a NEW ROOF * NEW Vinyl Siding & NEW 8-foot Tall GARAGE DOOR and Electronic Opener * along with extra storage space ******* Now I think I am done...Maybe! LOL....Oh Yeh.....I Did forget to Mention the Smart Thermostats AND There is a Fenced-in Yard with a Newly Cemented Patio that Provides Space for Outdoor Relaxation!!!!! ****** ALL THIS and Great Schools and Parks Nearby!!!!!!!!! ************* Which Makes this Property PERFECTION!!!! ********* ********* Nothing to do here but MOVE RIGHT IN!!!!!! ************ This is One of the Best Multi-Family Properties on the market and a Great Investment Opportunity!!!

5623 N Miltimore Avenue, Chicago
$655,100
7 Beds ⋅ 3 Baths ⋅ 12430366 MLS ⋅ CLOSED Status
Welcome to this beautifully renovated jumbo 2 flat located in the highly desirable Jefferson Park neighborhood. It boasts over 2,500 square feet of living space offering a perfect blend of style, comfort,and functionality making it ideal for homeowners or savvy investors. Gourmet kitchens with custom cabinetry, built in islands, range hoods and stainless steel appliances. Recessed lighting, gleaming hardwood floors throughout and high quality ceramic tiled bathrooms on every level. Separate utilities for each unit and central air conditioning for year around comfort. The finished basement offers a versatile layout with a large family room, bedroom & full bath.Renovation updates also include new drain tiles and a sump pump. , new roof, modern PVC siding installed on the entire building. Private backyard Oasis with with lovely paver stone landscaping, 2 car garage plus a carport. Located near top rated schools, O'hare, the Blue line, I90/94 Do not miss this exceptional opportunity to own this spacious, stylish and income generating property in one of Chicago's most sought after neighborhoods.

5351 W Foster Avenue, Chicago
$448,000
3 Beds ⋅ 2 Baths ⋅ 12419028 MLS ⋅ CLOSED Status
** MULTIPLE OFFERS RECEIVED BEST AND FINAL BY 8/3 NOON **.GREAT JEFFERSON PARK LOCATION. THIS WELL-CARED FOR CHARMING, SOLID 2 FLAT HAS GOOD BONES, HARDWOOD FLRS, CENTRAL AIR, ALL SEPARATE UTILITIES, ENCLOSED PORCHES, FULL UNFIN BSMT. EXTERIOR HAS NEWER SIDING & ROOF ON THE HOUSE & GARAGE(2012). BEAUTIFUL BACKYARD W/LGE PATIO, 30 FOOT LOT. SUPER LOCATION. CLOSE TO SHOPPING AND TRANSPORTATION!

5709 W Ainslie Street, Chicago
$550,000
4 Beds ⋅ 2 Baths ⋅ 12419475 MLS ⋅ CLOSED Status
Welcome to 5629 N Major Avenue - a rare opportunity offering flexibility, space, and long-term value in a prime Chicago location! Lovingly maintained by the same owner for 24 years, this solid brick 2-flat is ideal for investors, live-in owners, or multi-generational living. Both units feature 2 bedrooms, hardwood floors, large living rooms, and formal dining rooms. The second-floor kitchen was beautifully remodeled in 2019. The full basement provides shared laundry, generous storage, and potential for additional living or recreational space. Situated on an oversized 123 x 37 lot, the private yard is a true highlight with professional landscaping, a patio, and a fire pit - perfect for entertaining or relaxing. Live in one unit and rent the other, lease both for steady income, or create a comfortable home for extended family - the possibilities are endless. The property is ideally located in a desirable neighborhood near forest preserves, I-90 access, and both Metra and CTA lines for an easy commute. Turnkey, versatile, and filled with potential - schedule your private showing today!

5629 N Major Avenue, Chicago
$605,000
4 Beds ⋅ 2 Baths ⋅ 12402804 MLS ⋅ CLOSED Status
Legal 2-Flat in Prime Jefferson Park - Oversized Lot, Updated Units, and Unbeatable Location! Welcome to this beautifully maintained legal 2-flat brick home nestled in a quiet, tree-lined residential street in sought-after Jefferson Park. Situated on an oversized Chicago lot, this property offers comfort, space, and convenience - perfect for investors or owner-occupants alike. Both units feature 5 spacious rooms, including 2 bedrooms, 1 full bathroom, a den ideal for a home office, playroom, or breakfast nook, and a walk-in pantry for extra kitchen storage. Enjoy the charm of hardwood floors in the bedrooms, granite countertops in the kitchens, and the practicality of in-unit washers and dryers in both units. The large living and dining areas provide a welcoming flow and plenty of space for entertaining. Significant updates in 2019 include: New heating and cooling systems. Modern interior updates for a fresh, move-in-ready feel The home also features a full, unfinished basement offering excellent potential for additional storage, future expansion, or recreational space. Two car garage with an extra 2 parking spaces in the back. Located just a 10-minute walk to Jefferson Park and the Metra/CTA Blue Line station, with quick access to I-90/94, commuting is a breeze. One unit is currently rented, while the other is vacant-making it the perfect opportunity for a homeowner to move in or for a savvy investor to rent out both units. Don't miss this exceptional opportunity in one of Chicago's most desirable neighborhoods!

5043 W Argyle Street, Chicago
$750,000
8 Beds ⋅ 4 Baths ⋅ 12396676 MLS ⋅ CLOSED Status
Drop in showing this Sunday (7/13/25) from 12:00 PM to 2:00 PM - don't miss this fantastic opportunity! Incredibly spacious and unique 2-flat with additional finished basement (in law unit), situated on an oversized 50' wide lot in the highly sought-after Jefferson Park/Forest Glen neighborhood. This property lives like a massive single-family home and offers tremendous versatility and income potential. The main level boasts 3 generously sized bedrooms and 2 full bathrooms, including a recently renovated bath. Enjoy a bright and airy open-concept living and formal dining area, plus a fully updated kitchen featuring 42" cabinets, granite countertops, a large island, washer and dryer hook up, and stainless steel appliances. This property also boasts a sun-filled sitting room providing additional lounging space. The large primary bedroom offers excellent closet space. Upstairs, you'll find a bright and modern 3-bedroom, 6-room apartment with its own private entry, an oversized primary bedroom with walk-in closet, updated kitchen, and full tile bath. Separate utilities and central A/C make it ideal for rental-easily generating $1,800+ per month. The full finished basement offers flexible living quarters with a full bath, second kitchen, spacious living area, laundry, and an additional room that can serve as a bedroom, office, gym, or more. Basement space can be duplexed with the first floor or used as its own unit. Additional highlights include beautiful hardwood floors throughout, majority of windows are new and just installed within the last year, flood control system, freshly painted deck, and a charming side yard and rear deck. This is a rare opportunity-homes on double lots like this don't come around often. Endless possibilities for investors or owner-occupants!

5125 N La Crosse Avenue, Chicago
$475,000
6 Beds ⋅ 3 Baths ⋅ 12382226 MLS ⋅ CLOSED Status
Estate Sale-Sold As-Is. Jefferson Park classic all brick 2-flat on an extra-deep 30x155 lot offers exceptional potential for investors or owner-occupants. Each spacious unit features a bright living room, formal dining room, three generously sized bedrooms, and an eat-in kitchen with pantry. Hardwood floors flow throughout the main living areas. Enclosed rear porch adds valuable storage. The partially finished basement includes bathroom and offers additional living space possibilities. Recent mechanical updates include a newer hot water boiler and heater. Enjoy the expansive backyard and a detached 2-car garage. Prime location near Jefferson Park Metra and Blue Line stations, I-90, parks, schools, dining, and shopping. Don't miss this rare opportunity!

5330 W Foster Avenue, Chicago
$905,000
8 Beds ⋅ 4 Baths ⋅ 12383023 MLS ⋅ CLOSED Status
Rare Opportunity !!! Home and/or Investment !!! Attractive solid brick 4-flat on double lot with basement in-law unit, plus 2-car garage & additional 2 parking spaces !! Large apartments ** Individually heated ** Hardwood floors ** Recent improvements include tuck pointing & newer windows ** Extra income from garage & coin laundry (1 washer/1 dryer) ** Long-time tenants - below market rents ** Great location near parks, schools, shopping & public transportation ** Being sold "As Is"

5851 W Eastwood Avenue, Chicago
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Jefferson Park, Chicago IL · Curated MLS Search

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