View All Jefferson Park Chicago IL Multi-Family Homes Listings

$649,900
4 Beds ⋅ 3 Baths ⋅ 12746405 MLS ⋅ NEW Status
**Beautifully Maintained All-Brick Two-Flat in Desirable Jefferson Park! Well-maintained all-brick two-flat featuring 2 generous 2-bedroom, 1-bath units ~Each unit offers a spacious living room, formal dining room, eat-in kitchen, and a versatile den that can be used as an office, craft room, or additional living space ~Vintage charm throughout includes Craftsman-style oak doors, trim, crown molding and hardwood floors. The finished basement provides an additional full bathroom and laundry area, offering excellent flexibility and storage ~Enjoy outdoor entertaining in the private, fenced yard, ~Oversized two-car garage for parking ease **Prime location easy access to bus service, the CTA, Metra, and I-90/94. Jefferson Park offers an array of restaurants, shops, parks, and neighborhood amenities ~Updates over the years include: Gutters and roof(2 yrs) with Ice melt system, Water heater (2 yrs), 1st floor kitchen, Vinyl windows on second floor, ~Electric Panels ~Tuck-pointing ~Garage door and opener ~Excellent opportunity to live in one unit and rent the other! This home has been maintained over the years but is being sold AS-IS.

4984 N Major Avenue, Chicago
$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
$575,000
4 Beds ⋅ 3 Baths ⋅ 12754787 MLS ⋅ NEW Status
City-certified two-flat in the heart of Gladstone Park offering exceptional flexibility for investors, owner-occupants, or multi-generational living. Thoughtfully updated over the years, this well-maintained property features remodeled kitchens and bathrooms on both the first and second floors, along with an updated first-floor primary bedroom. Each unit offers comfortable living space, while the second-floor apartment features two private entrances and an expanded rear deck overlooking the beautifully landscaped yard. A partially finished basement includes an in-law suite, with 1 bedroom and 1 full bath providing additional flexible living space. Outside, you'll find a true urban oasis with raised garden beds, fruit trees, a patio, and mature landscaping that creates a private retreat. The insulated 2.5-car garage was fully rehabbed in 2023 and offers excellent storage or workshop potential. Additional improvements include newer windows, hardwood floors, and numerous updates throughout. Interior stairs connecting the first and second floors remain behind the dining room wall, offering the potential for a future single-family conversion if desired. This versatile property combines income potential, beautifully maintained outdoor space, and a prime Gladstone Park location. Property is being sold As-Is.

5942 W Thorndale Avenue, Chicago
$579,900
5 Beds ⋅ 3 Baths ⋅ 12754676 MLS ⋅ NEW Status
What a yard! Gorgeous frame 2 unit spanning 2 lots in Jefferson Park side of Portage Park Chicago. Fully enclosed, this double lot has mature landscaping, an oversized garage, raised patio and additional storage shed. It doesn't lack hang out space nor growing space! This 2 unit has a partially finished basement with a bedroom/bar setup and full bath. The attic is unfinished with further expansion potential. The second floor has central heat and air with a brand new condenser and updated fridge. It features all hardwood, original hutch and high ceilings. Most of the windows have been updated in the last 15 - 20 yrs. Roof estimated 10-15yrs old. The 1st floor is boiler heated with 2 large bedrooms and a big kitchen with back sunroom. This unit is in need of some TLC. Unit 1 and garden are vacant and ready while 2nd floor's lease ends in Feb. 28th 2027. Great location by greenspace, walk to the Metra, bus and Jeff Park Blue line transit center and just 2 blocks from Jewel, great dive bars, Starbucks, Prussing Elementary, great Pilipino and Polish restaurants.. ALL within a 5 minute walk...

5753 W Giddings Street, Chicago
$655,000
4 Beds ⋅ 2 Baths ⋅ 12751659 MLS ⋅ ACTIVE 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
$585,000
4 Beds ⋅ 2 Baths ⋅ 12751624 MLS ⋅ ACTIVE Status
Opportunity awaiting! Chicago's desirable Jefferson Park, two units property with a two car garage. Unit one features two bedrooms and one bathroom, unit two also offers two bedrooms and one bath. Basement is unfinished waiting for your ideas. Property is habitable needs work and is sold AS IS.

4855 N Mcvicker 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
$650,000
6 Beds ⋅ 3 Baths ⋅ 12565108 MLS ⋅ CONTINGENT Status
Pride of Ownership. Well-maintained multi-unit property located on a quiet tree-lined street within Chicago's Portage Park/Jefferson Park corridor. This multifamily building sits on an oversized 35' x 125' lot. Each unit features a three-bedroom, one-bath layout. Hardwood floors throughout the first floor living, dining, and bedrooms. 2nd Flr features original hardwood floors beneath wall-to-wall carpeting.2nd Flr Kitchen Linoleum Tiles. Enclosed porches provide additional space suited for an office or a variety of additional uses. Plenty of closet capacity and storage options. Building amenities include coin-operated laundry in the basement, Three Separate Storage RoomsThe oversized lot affords a rear yard for gardening and recreation. Property includes a full two-car garage with a side drive for a third vehicle. Prime location provides excellent access to transportation, including the Jefferson Park and Montrose Blue Line stations and Metra stops, and the Jefferson Park CTA Depot. Easy access to I-90/94 for easy travel to O'Hare or downtown. Located near parks, shopping, and neighborhood amenities. Two leases are month-to-month. First floor is vacant. Current rents are well below market, and the area supports significantly higher rental rates. ROOF 9YRS FURNACES 2 YEARS NEW.

5048 W Agatite 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
$769,000
6 Beds ⋅ 3 Baths ⋅ 12736664 MLS ⋅ ACTIVE Status
**Rare Jefferson Park Multi-Unit Opportunity!** Owned and cared for by the same family for more than 30 years, this well-maintained property offers an incredible combination of space, income potential, and location just down the block from Dunham Park. Situated on an oversized approximately **50' x 190' lot**, this **legal 2-unit with garden-level living space** is currently being enjoyed by the seller as one expansive single-family residence-showcasing just how much living space this property provides. Featuring approximately **6 bedrooms and 3 bathrooms throughout the building**, the layout includes 2 bedrooms on the second floor, 3 bedrooms on the first floor, and 1 bedroom at the garden level. The property offers **central heat and air**, new driveway, 3 year old roof, generous living areas, and has been lovingly maintained throughout its longtime family ownership. Outside, the property continues to impress with a **long driveway, garage, and additional land beyond the garage**, a combination rarely found in this part of the city. **Longtime ownership. Oversized lot. Multiple income possibilities. Prime Jefferson Park location near Dunham Park.** A unique opportunity for investors, owner-occupants, and multi-generational families alike.

6134 W Leland 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
$525,000
6 Beds ⋅ 4 Baths ⋅ 12703033 MLS ⋅ CLOSED Status
Rare opportunity to purchase a legal 4 unit in Jefferson Park in highly sought after Beaubien elementary! A well maintained building that has been cared for over 30 years by the current owners, the property offers (two) 2 bed 1 bath units and (two) smaller 1 bed 1 bath units. The top front unit has in unit washer/dryer and is a duplex up that expands to the attic with 2nd bedroom, skylight, and huge walk in closet. Very attractive building with below market rents and separate utilities with tenants paying their own gas and electric. Each unit is equipped with newer wall furnaces, newer hot water tanks, and hardwood floors or LVP/laminate. Solid architectural shingled roof that is 13 years old, mostly vinyl windows, 200 amp electrical, and most waterlines have been upgraded to copper with booster pump. Tall two car garage is leased for $250/month for additional income. Incredible Jefferson Park location with easy highway access and nearby Metra and CTA Blue Line.

4849 W Ainslie 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
$590,000
5 Beds ⋅ 3 Baths ⋅ 12701869 MLS ⋅ RE-ACTIVATED Status
3 Total Dwelling Units Multi-Family building (zoning RS-3 on recent Zoning Certificate attached in Additional Info) on an oversized double Lot (6,250 Sq Feet) right in the heart of Jefferson Park. Attention: Rehabbers, Developers (for Value in the Land). Also, for Homeowners/Owner Occupied to live in one apartment and rent out two other units. 3 units comprise: Two smaller 2bed/1 bath apartments in divided 1st Floor. And on the 2nd Floor, one 2 bedrm/ 1 bath apartment with Living Rm/Family Rm and Dining Room. Full unfinished basement is just an open space with mechanicals and laundry room. Newer roof was installed in 2022. 2 car garage. Plus an additional rent from 3 parking spaces.

5484 W Gettysburg Street, Chicago
$599,000
5 Beds ⋅ 3 Baths ⋅ 12699951 MLS ⋅ ACTIVE Status

4542 N Long Avenue, Chicago
$399,900
4 Beds ⋅ 3 Baths ⋅ 12693972 MLS ⋅ CONTINGENT Status
"BACK ON THE MARKET - Buyer got cold feet. Their loss is your buyer's gain!" Bring your vision and creativity to this classic brick two-unit property offering exceptional flexibility, generous living space, and outstanding potential in one of Chicago's most desirable Northwest Side neighborhoods. Whether you envision living in one unit while generating rental income from the second, creating the perfect multi-generational home, or transforming the property into a spacious single-family residence, this home offers endless possibilities to match your lifestyle and goals. Featuring a total of 4 bedrooms, 3 full bathrooms, and a full basement, this property provides the solid foundation to create something truly special while adding your own personal style and finishing touches. Inside, you'll find spacious living areas filled with natural light and traditional layouts that provide excellent functionality. Each unit offers comfortable living and dining spaces, well-sized bedrooms, and kitchens ready to be redesigned and customized to today's preferences. The flexible floor plan allows future owners to preserve the two-unit configuration or reimagine the property as one expansive residence. The full basement adds tremendous value, providing abundant storage space, a dedicated laundry area complete with washer and dryer, and additional room that could serve a variety of future uses, including recreation space, a workshop, hobby area, fitness room, or expanded living space, subject to local requirements and approvals. Outside, the classic brick exterior offers timeless curb appeal and durable construction that continues to be highly desirable. The yard provides space for gardening, outdoor entertaining, summer gatherings, or simply enjoying your own private outdoor retreat. Whether your vision includes enhancing the landscaping or creating additional outdoor living areas, the property offers plenty of opportunity to make it your own. The location is equally impressive. Situated in one of Chicago's most established residential neighborhoods, this home offers convenient access to parks, recreational facilities, shopping, dining, grocery stores, coffee shops, and everyday conveniences. Nearby Portage Park and Jefferson Memorial Park provide green space, athletic facilities, playgrounds, tennis courts, swimming, and year-round recreational activities. The neighborhood is known for its mature tree-lined streets, strong community atmosphere, and well-maintained homes that continue to attract buyers looking for long-term value. Commuters will appreciate the excellent transportation options, including nearby CTA bus routes, Metra service, and quick access to Interstate 90/94, providing convenient travel to downtown Chicago, O'Hare International Airport, and surrounding suburbs. The home is also close to the Six Corners shopping district, forest preserves, golf courses, entertainment venues, restaurants, and a wide variety of retail destinations that make daily living both convenient and enjoyable. Whether you're looking for the flexibility of owner-occupied living with additional rental potential, space for extended family, or the opportunity to create a beautiful single-family home, 5160 W Sunnyside Ave offers the layout, location, and potential to bring your vision to life. With its solid brick construction, 4 bedrooms, 3 full bathrooms, full basement, and highly desirable Northwest Side location, this property is ready for its next chapter and presents an outstanding opportunity to create a home tailored to your lifestyle while building lasting value.

5160 W Sunnyside Avenue, Chicago
$700,000
5 Beds ⋅ 3 Baths ⋅ 12675885 MLS ⋅ CLOSED Status
**Rarely Available Legal 3 Unit**Very Well Maintained building located in prime Portage Park location near groceries, restaurants, transportation (The Jefferson Park blueline is approximately 5 blocks away. 90/94 is also approximately 5 blocks away) and walking distance to Starbucks & Dunkin Donuts. **Major **Building **Upgrades in 2025 include all new windows in all 3 units (windows in back porch unchanged); New main electric service upgraded to 200 amp as well as new public electric panel added and all 4 new individual panels upgraded to 100 amp; New water heater Unit 2 (Unit 1 WH replaced 2023 and Unit G WH replaced 2019); Unit 1 (2bd/1bth) thoughtfully updated with the following: completely painted, bath updated (new vanity, toilet, shower/sink fixtures, exhaust fan, mirror and light), kitchen completely updated with solid white oak soft close cabinets, quartz counters, black sink and fixtures, backsplash, and all new black appliances (GE Fridge, Stove, Microwave, Dishwasher, and LG **In-unit washer/dryer**), sanded floors in white oak, 3 new window AC units, all new light fixtures, all new blinds, and more. Unit G Bath updated (New tub, toilet, vanity, mirror, light fixture, exhaust fan, and shower/sink fixtures). Rents - Unit G (1bd/1bth) - $1,050; Unit 1 (2bd/1bth) includes 2 car garage - $2,350; Unit 2 (2bd/1bth)- $1625; Roof is approximately 5-7 years old. Brick exterior is in immaculate condition. **Tenants pay their own light and gas as the building has **3 separate water heaters , **3 separate boilers, **3 separate gas meters, and **4 electric meters. Building is solid and clean - offers should be made as-is with no requests. Zoning Cert and Building Info Sheet available in additional information tab.

4614 N Central 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
$522,500
5 Beds ⋅ 3 Baths ⋅ 12673635 MLS ⋅ CLOSED Status
Bright and sunny Dutch Colonial two-unit building with an in-law unit in Portage Park on an oversized lot. Each unit offers 2 large bedrooms divided by updated bathrooms with an in-law suite in the basement that includes a flexible one bedroom/studio with a seperate bathroom and living room. The property now includes modern heating and cooling systems in all three living areas including ductwork. Unit 1 had additional updates including beautiful hardwood and subfloors, a new bathroom (including tile, floor, toilet, sink and lighting), dishwasher added to the kitchen and was painted in April 2026. Excellent care has been taken over the years including exterior work on the porch and adding a new front and back gate. There are two hookups for laundry in the basement and 1 washer and dryer are included in the sale. The building has a beautiful backyard ideal for entertaining and pets. This is an ideal house hacker or any first time investor looking to live for pennies. Location has strong long term income potential in charming Portage Park close to restaurants, bars, shopping and many cute neighborhood parks.

5725 W Giddings Street, 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
$600,000
5 Beds ⋅ 3 Baths ⋅ 12647973 MLS ⋅ CLOSED Status
Prime Portage Park location! Move-in ready property offering great space, solid bones, and excellent natural light. Ideally located in the middle between Downtown Chicago and O'Hare Airport right off the Kennedy Expressway (I-90/94). Conveniently situated near public transportation (CTA Blue Line & Montrose bus), top-rated schools, parks, and vibrant local dining/shopping. 1st floor is duplexed with the lower level, adding additional living space, 2 bedrooms, a 2nd kitchen, and a full bathroom. Rare opportunity-it won't last long!

4916 W Montrose Avenue, Chicago
$662,000
6 Beds ⋅ 3 Baths ⋅ 12655153 MLS ⋅ CLOSED Status
Decades of prideful ownership, consistent upkeep, and proactive maintenance are evident in this exceptionally well-cared-for multi-unit property located on a quiet, tree-lined street. Perfectly positioned within Chicago's sought-after Mayfair/Portage Park/Jefferson Park corridor, this multifamily opportunity sits on an oversized 35' x 125' lot, offering expanded outdoor living and future flexibility. Each unit features a desirable 2-bedroom, 1-bath layout. The 1st and 2nd floor residences showcase sun-filled interiors, expansive living rooms, separate formal dining areas, and natural hardwood flooring extending throughout the living/dining spaces and bedrooms. Enclosed rear porches provide versatile flexible areas well-suited for a home office, den, storage, or a variety of additional uses. The second-floor unit also includes a front balcony, creating another private outdoor retreat. Abundant closet capacity and storage options add further functionality throughout the building. Separate HVAC systems and individual hot water tanks for each unit provide efficiency. Building amenities include coin-operated laundry in the basement along with dedicated storage areas for each residence. Major improvements include heating mechanicals and garage roof all 10 years old or newer, central air conditioning replaced in 2022 and 2024, and flood control system installed in 2024. Long-term ownership is reflected in the continued care and ongoing significant investments made throughout the years. The oversized lot further enhances the property with an expansive side/rear yard for gardening, entertaining, recreation, or future possibilities. Rounding out the exterior is a full 3-car garage.This prime location provides excellent access to transportation including the Jefferson Park and Montrose Blue Line stations & Metra stops, Jeff Park CTA depot, and convenient access to I-90/94 for easy travel to O'Hare and downtown Chicago. Located near parks, shopping, dining, and neighborhood amenities, this is a rare opportunity to own a solid, well-maintained building with decades of attentive ownership in an exceptionally convenient location. Your clients will not be disappointed. 2 leases are MTM, other expires in August.

5041 W Agatite 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
$660,000
4 Beds ⋅ 3 Baths ⋅ 12650518 MLS ⋅ CLOSED Status
Well-maintained 2-unit property with a finished in-law basement, offering great flexibility for owner-occupants or investors alike. The second-floor unit features 1 bedroom, a spacious living room, formal dining room, updated kitchen with stainless steel appliances, and hardwood floors throughout. The first-floor unit also offers 2 bedrooms, a bright living room, dining room, kitchen with stainless steel appliances, and hardwood flooring. The updated in-law basement includes 1 bedroom, living room, dining area, and additional living space perfect for extended family or related living arrangements. Additional improvements include a newer garage and a check valve installed approximately 2 years ago. Conveniently located near shopping, schools, transportation, and more. Great opportunity to own a versatile multi-unit property with strong rental potential.

4915 W Winnemac 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
$376,200
6 Beds ⋅ 3 Baths ⋅ 12631781 MLS ⋅ CLOSED Status
Rarely does an opportunity this versatile hit the Jefferson Park market! This massive three-unit building is an investor's dream, perfectly suited for a high-end flip, a steady rental addition, a BRRRR project, or the ultimate house hack. Each unit features a spacious 2-bedroom, 1-bathroom layout, complemented by a massive basement that offers incredible potential to be finished for additional living space or increased cash flow. The property also includes a two-car garage, providing even more value and revenue potential. Situated in a premier location within walking distance of top-rated schools, lush parks, and vibrant shopping districts, this property checks every single box for savvy buyers. Opportunities in this sought-after pocket don't last-schedule your showing today and secure your next big win!

5032 W Gunnison Street, Chicago
$810,000
8 Beds ⋅ 5 Baths ⋅ 12626154 MLS ⋅ CLOSED Status
Exceptional multi-unit investment opportunity at 5754 N. Elston in Chicago! This unique property features 2 units, with duplex down offering incredible income potential and flexibility for investors or owner-occupants alike(2 total units). This completely renovated property offers immediate cash flow potential or the flexibility to live in one unit while renting out the other. The building features multiple units, including a fully finished duplex down with 3 bed/ 2 bath up and 2 bed down/1 bath down. Upper unit, offering 3 bed/2 bath layouts, and each with spacious living spaces. Outside, a outdoor balcony in both units and a large parking pad with space for up to 3 vehicles- an added convenience for tenants or owners. Located in a highly desirable commuter-friendly area, the property is within walking distance to the Jefferson Park Transit Center, providing access to the CTA Blue Line, Metra, and Amtrak. Close to Kennedy Expressway and the Edens Expressway, making travel throughout the city and suburbs effortless. Downtown Chicago is approximately 11 miles away, and O'Hare International Airport is just 6 miles from the property. The property is also located within the boundaries of Farnsworth Elementary School and Taft High School. Don't miss this rare opportunity to own a versatile, income-generating property in a prime Chicago location!

5754 N Elston Avenue, Chicago
$740,000
8 Beds ⋅ 3 Baths ⋅ 12621770 MLS ⋅ CLOSED Status
Beautifully updated 3-flat located in the highly desirable Jefferson Park neighborhood of Chicago. Each unit offers three spacious bedrooms, modern finishes including granite countertops throughout, and updated shaker cabinetry. Enjoy the convenience of in-unit laundry in every apartment, along with central heating and air. The property also features a shared rear deck with ample street parking is readily available. Ideally situated just minutes from Harlem Irving Plaza, offering easy access to shopping, dining, and everyday conveniences. Don't miss this great property before it's gone! HIGHEST AND BEST DUE 4/20/2026 AT 1PM.

6030 W Lawrence Avenue, Chicago
$790,000
4 Beds ⋅ 3 Baths ⋅ 12619804 MLS ⋅ CLOSED Status
Welcome to this beautifully maintained all-brick two-flat located in the desirable Jefferson Park neighborhood! Each spacious unit features two bedrooms plus an additional bonus room off one of the bedrooms-ideal for a home office, nursery, or reading nook. Both updated baths offer modern finishes and heated floors, while the separate living and dining rooms provide bright, comfortable spaces full of classic Chicago character. The property also includes a finished basement, perfect for additional living space, storage, or an in-law arrangement. Pride of ownership is evident throughout, with thoughtful updates and meticulous maintenance inside and out. Enjoy a well-kept yard, a two-car garage, and an additional carport offering extra parking convenience. Located just minutes from the Jefferson Park CTA Blue Line and Metra station, this property provides quick access to I-90/94 for easy commuting downtown or to the suburbs. The neighborhood offers a great mix of restaurants, coffee shops, and local parks-all contributing to a warm, community feel. Whether you're looking for an owner-occupied home with income potential or a solid investment property, 5536 N Mango delivers space, comfort, and accessibility in one of Chicago's most connected neighborhoods.

5536 N Mango 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
$775,000
6 Beds ⋅ 3 Baths ⋅ 12606995 MLS ⋅ CLOSED Status
Perfect Opportunity for First-Time Buyer or Investor to own a 3 Flat in an Ideal Jefferson Park location! Close proximity to the award-winning Beaubien Elementary School and Taft High School! Park & playground is one block to the west, and CTA and Metra stops are just a few blocks and a short walk away. First time on the market in 39 years! Owner-occupied and/or Family-Occupied that whole time, and the renovations and improvements have been continuous. All three units offer individual furnaces and central AC, updated kitchens & baths, beautiful hardwood or bamboo floors, newer thermopane windows. Roof was a complete tear-off in 2020. Relax with a drink on the rebuilt front porch, or BBQ and entertain family/guests on the rear patio while admiring the perennial gardens. The owners will have the above ground pool removed prior to closing. Whether you are looking for your next investment, or are simply looking for a more affordable way to buy a home to live in, this property is ideal! Call/text to schedule your viewing today!

5055 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
$650,000
5 Beds ⋅ 2 Baths ⋅ 12594247 MLS ⋅ CLOSED Status
***Multiple offers received, best and final due Saturday 3/28 at 12:00 noon***Welcome to this well-maintained legal 2-unit property with additional finished basement living space located in the highly desirable Jefferson Park neighborhood of Chicago. This versatile building is perfect for investors or owner-occupants looking to generate strong rental income. The property features: Unit 1 (Main Floor): Spacious layout with 3 bedrooms, 1 full bath, a bright living room, and a full kitchen-ideal for comfortable family living. Unit 2 (Second Floor): Well-appointed 2-bedroom, 1 bath unit with a cozy living room and full kitchen, offering excellent rental potential. Currently rented. Finished Basement: Includes 3 bedrooms, 1 full bath, kitchen, and laundry room. Currently, 2 of the 3 bedrooms are rented, providing immediate income. This property offers multiple income streams with flexibility for continued rental use or potential owner occupancy. The basement setup enhances cash flow, making this an attractive option for investors seeking strong yield in a prime Chicago location. Conveniently located near public transportation, shopping, dining, and major highways, this property combines location, functionality, and income potential. Don't miss this opportunity to own a high-performing multi-unit in one of Chicago's most sought-after neighborhoods!

5428 W Sunnyside Avenue, Chicago
$532,000
5 Beds ⋅ 3 Baths ⋅ 12588296 MLS ⋅ CLOSED Status
Multiple offers have been received. Seller is asking for highest & best offers by Wednesday 03/18 at 12noon. Amazing Jefferson Park multi-unit investment opportunity perfectly positioned between I-90 & I-94 and close to Jefferson Park Metra and CTA transit depot, this well-maintained three-unit property delivers an unbeatable combination of location, income potential, and long-term value. Highly sought after location neighboring Sauganash, Forest Glen, Portage Park, Mayfair and conveniently located near restaurants & shopping, Gale Street Inn, Whole Foods, Target, Seafood City, Starbucks, etc. and highly rated Beaubien Elementary School consistently ranked among Chicago's top schools just 3 blocks away. This is an ideal opportunity with many options: live-in one unit and generate income leasing the other units OR perfect for seasoned investors to add to their portfolio. Also, a great space for multi-generational living. The building features two spacious 2-bedroom, 1-bathroom units with large and spacious kitchens plus an additional garden-level unit with lots of natural light, all with separately metered utilities paid by tenants. Significant recent upgrades include a new roof (2024) on both the main building and the detached 2-car garage, a newer garage door, several windows replaced, thermo-coils and fans replaced in wall heaters and 1 new hot water heaters (2024). All bedrooms feature original hardwood floors. Common area shared large deck and backyard plus on-site laundry. All units have had successful rental history. Immediate income potential and significant upside for the next owner. Seller and Broker do not represent that the garden unit is a legal or permitted dwelling unit. Buyers are advised to verify legality, zoning, and compliance with local authorities prior to purchase. Selling as-is

4940 W Ainslie Avenue, Chicago
$699,900
6 Beds ⋅ 3 Baths ⋅ 12559681 MLS ⋅ CLOSED Status

5113 W Strong Street, Chicago
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