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$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
$585,000
4 Beds ⋅ 2 Baths ⋅ 12751624 MLS ⋅ NEW 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
$635,900
5 Beds ⋅ 3 Baths ⋅ 12748438 MLS ⋅ NEW Status
NICE JEFFERSON PARK 2 FLAT WITH FINISHED BASEMENT! 2 OVERSIZE UNITS WITH CENTRAL AIR, THREE SEPARATE FURNACES AND HOT WATER TANKS, COPPER PLUMBING. BOTH UNITS HAVE FORMAL DINING ROOM, DEN AND SLIDING DOOR TO THE DECK! NEWER WIDOWS, NEWER 1ST FLOOR AC UNIT,TWO FURNACES AND WATER TANKS ARE NEWER TOO. 2 CAR GARAGE AND ADDITIONAL PARKING SPOT. COIN LAUNDRY. GREAT RES BLOCK! THE PROPERTY IS IN A GREAT SHAPE BUT SELLER WANTS TO SELL IT AS IS.

5475 N Monitor Avenue, Chicago
$599,000
6 Beds ⋅ 3 Baths ⋅ 12746363 MLS ⋅ NEW 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 ⋅ ACTIVE 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 ⋅ ACTIVE 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
$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
$539,900
4 Beds ⋅ 2 Baths ⋅ 12740981 MLS ⋅ ACTIVE Status
Fantastic investment opportunity in the desirable Jefferson Park neighborhood-a well-maintained and updated 2-flat that offers both turnkey investment potential and the option for owner-occupancy. Each unit features 2 bedrooms and 1 bathroom, complemented by beautiful hardwood floors, central HVAC, and a bonus back porch. The main floor unit boasts modern upgrades, including stainless steel appliances, maple cabinetry, and new light fixtures. Both units have separate utilities, ensuring convenience and privacy. The unfinished lower level provides dedicated laundry spaces, mechanical systems, and open storage for each unit. Additionally, there is a detached 2.5 garage currently leased to a neighbor, adding extra income potential. Situated on a quiet, tree-lined street, this property is within walking distance to the Gladstone Park Metra station, offers quick highway access, and is close to schools, parks, restaurants, and shopping. Current tenant leases expire in December 2026 and June 2027.

5848 W Catalpa 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
$574,900
5 Beds ⋅ 3 Baths ⋅ 12736554 MLS ⋅ ACTIVE 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
$599,999
3 Beds ⋅ 2 Baths ⋅ 12710112 MLS ⋅ ACTIVE 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, 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
$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 ⋅ ACTIVE 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
$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
$649,900
5 Beds ⋅ 3 Baths ⋅ 12647973 MLS ⋅ ACTIVE 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
$734,900
5 Beds ⋅ 3 Baths ⋅ 12503023 MLS ⋅ ACTIVE Status

5600 N Mango Avenue, Chicago



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