Newest Jefferson Park Multi-Family Listings

8 Beds ⋅ 3 Baths ⋅ 12800850 MLS ⋅ NEW Status

QUALITY BUILT YELLOW BRICK LEGAL 3 FLAT W/2.5 CAR GARAGE IN JEFFERSON PARK. HARDWOOD FLOOR ,LONG TERM TENANTS. NEEDS COSMETIC UPDATES. ADDITIONAL INCOME FROM GARAGE $300.00. WALKING DISTANCE TO ALL SHOPS, TRANSPORTATION & X-WAY. GREAT AREA.

5420 W Montrose Avenue, Chicago

$579,000

4 Beds ⋅ 3 Baths ⋅ 12798459 MLS ⋅ NEW Status

Excellent opportunity to own this well-maintained brick 2-flat with a non-conforming 3rd unit in the basement. All units have 2 bedrooms & 1 bath! This property offers spacious layouts, nice floor plans, quality updates, & excellent income potential! Special unit feature on 1sr floor include: Hardwood floors, pantry, central air & a spacious deck overlooking the yard; 2nd floor has hardwood floors, central air, spacious pantry, and a lovely enclosed porch. Additionally there are thermopane windows throughout the bldg, 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 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 at the corner! Lovely Neighborhood Location!

5839 W Eastwood Avenue, Chicago

$689,000

4 Beds ⋅ 2 Baths ⋅ 12798118 MLS ⋅ NEW Status

Welcome to 5548 N. Major Avenue, located in the heart of Chicago's Jefferson Park neighborhood! This well-maintained two-flat building offers excellent flexibility for owner-occupants, investors, or multi-generational living. Both units feature new flooring throughout, while the second-floor unit shines with a newly remodeled kitchen and bathroom. The bedrooms are sizable, and ample closet space is found throughout, featuring additional coat closets, pantry, and linen closets. Each unit includes individual central air conditioning and gas forced heat. The property also features a basement ready to be finished, offering endless possibilities for an additional in-law suite or duplex-down expansion. Major improvements include new electric service to the building, new water heater, a roof approximately 5 years old, newer windows, and a completely rebuilt garage featuring an impressive 12-foot ceiling and a brand-new rooftop deck above the garage. Enjoy the outdoor space with a charming brick patio in the rear yard, perfect for entertaining or relaxing. With significant updates already completed and tremendous potential to add even more value, this property is a fantastic opportunity to own a versatile two-flat in Chicago!

5548 N Major Avenue, Chicago

$619,999

6 Beds ⋅ 3 Baths ⋅ 12796977 MLS ⋅ NEW Status

Ready to begin cash flowing? This fully vacant freshly renovated 6 bedroom 3 bathroom 2-Unit building with a finished basement is missing one thing, YOU! Entire building has spacious bedrooms, tons of natural light, updated appliances, recess lights, new flooring, new central heat, new windows, tankless water heaters and everything else you will need. Downstairs unit duplexes into the finished basement giving you a massive 4 bedroom 2 bathroom in law apartment.

4457 N Lamon Avenue, Chicago

$740,000

8 Beds ⋅ 5 Baths ⋅ 12796696 MLS ⋅ ACTIVE Status

OVER $200,000 IN IMPROVEMENTS over the last three years! This is not a flip, just a well-managed and exceptionally improved opportunity in Jefferson Park featuring a legal 2-flat with a finished English garden unit. A rare find! Especially with BOTH upper units offering 3 bedrooms and 1.5 baths. Extensively updated in 2024-2025, this turnkey property delivers the space, condition, and income potential investors and owner-occupants are looking for. Both legal units feature spacious layouts, separate dining rooms, additional kitchen/dining areas, recessed lighting, and beautifully updated kitchens with quartz countertops, stainless steel appliances, and ample cabinetry. Updated bathrooms and modern finishes make these units stand out. The improvements go well beyond cosmetics, including a new roof, windows, gutters, tuckpointing, flooring, kitchens, bathrooms, and an upgraded rooftop deck over the garage-all completed in 2024-2025. Enjoy the benefits of substantial recent investment without the immediate expense of major renovations. The income is already working for you! Unit 1 is leased at $2,650/month, and Unit 2 at $2,400/month, generating $5,050/month or $60,600 annually in current gross rental income. The finished garden unit is currently vacant and offers 2 bedrooms and 1 full bath, presenting additional flexibility for an owner-occupant, extended household, or potential rental income, subject to applicable zoning, permits, and legal occupancy requirements. If approved for rental use, estimated rent of $2,300/month could bring potential gross income to $7,250/month or $87,000 annually. Explore the short-term rental opportunity! AirDNA market data provided by the seller indicates an average daily rate of $116 and 69% occupancy. At those market benchmarks, a qualifying short-term rental could generate approximately $29,200 in gross annual booking revenue for one unit. Combined with the existing leases, the property presents a potential gross revenue opportunity of approximately $89,800 annually, assuming the garden unit is legally approved for short-term rental use and achieves the stated market performance. Actual results will vary, and gross revenue excludes operating expenses. Additional features include rear decks, a rooftop deck over the 2-car garage, shared outdoor space, and coin-operated laundry. Enjoy convenient access to the Kennedy Expressway (I-90/I-94), O'Hare International Airport, and the Jefferson Park transportation hub, with CTA Blue Line and Metra connections. Nearby shopping and everyday conveniences include Jefferson Park Plaza, Gladstone Corners, Mariano's, and Jewel-Osco, along with neighborhood restaurants, cafes, parks, and local businesses.

5759 N Elston Avenue, Chicago

$579,000

4 Beds ⋅ 3 Baths ⋅ 12793590 MLS ⋅ ACTIVE Status

Beautiful, Legal Brick 2 Flat in the heart of Jefferson Park. Excellent building includes top floor unit 2 Bed 1 Bath. First floor unit 2 Bed 1 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. In-law arrangement with additional Bed and Bath. 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

$670,000

6 Beds ⋅ 3 Baths ⋅ 12787200 MLS ⋅ ACTIVE Status

Wonderful Opportunity in the Heart of Jefferson Park! Discover the possibilities with this charming 2-flat situated on an oversized lot along a beautiful, tree-lined street in one of Chicago's sought-after Northwest Side neighborhoods. Whether you're an investor looking to expand your portfolio or an owner-occupant hoping to live in one unit while generating rental income from the other, this property offers flexibility and exciting potential. The generous lot provides additional outdoor space and opportunities to create your own backyard retreat. Enjoy the charm of an established neighborhood while being just moments away from everything you need. The location is truly a highlight! Conveniently situated near neighborhood parks, shopping, restaurants, Jewel-Osco, the CTA Blue Line, Metra, and I-90, with easy access to O'Hare International Airport. With its desirable location, oversized lot, and investment potential, this property is a wonderful opportunity to bring your vision to life and make it your own. Schedule your showings today!

5122 N Lotus Avenue, Chicago

$549,900

4 Beds ⋅ 2 Baths ⋅ 12785670 MLS ⋅ ACTIVE Status

Charming Gladstone Park two-flat situated on a desirable corner lot directly across from Gladstone Park! This well-maintained property features two updated units with separate utilities, refreshed kitchens, tile baths, and refinished hardwood floors. The first-floor unit offers an inviting open living space, forced-air heat, and central air conditioning, while the second-floor unit features gas hot water heat and a wall-mounted AC unit. Enjoy a spacious front porch, a lovely yard, and a two-car garage with a covered patio. Conveniently located within walking distance of the Blue Line and Metra, offering easy access to downtown Chicago. A fantastic opportunity for investors or owner-occupants in a great neighborhood! Additional income: $250/month for garage and approx $50/mo for laundry.

5377 N Magnet Avenue, Chicago

$739,000

5 Beds ⋅ 3 Baths ⋅ 12783248 MLS ⋅ ACTIVE Status

5626 N Central Avenue, Chicago

$583,000

4 Beds ⋅ 2 Baths ⋅ 12779923 MLS ⋅ ACTIVE Status

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

5334 N Lovejoy Avenue, Chicago

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Jefferson Park Multi-family Real Estate For Sale

Thinking about buying or selling a Jefferson Park multi-family building? We have 16 years of experience selling multi-family properties in the area. Our experience and market knowledge will help you achieve your goals and avoid pitfalls.

Multi-family real estate in Jefferson Park is currently one of the hot trending neighborhoods. First time buyers and seasoned investors are competing for properties, especially for two flats and three flats. Jefferson Park is sought after due to its ideal location in the Northwest side of Chicago and easy access to public transportation.

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Jefferson Park 2 Flats, 3 Flats & 4 Flats

While the majority of Jefferson Park homes are single family homes, there are great opportunities in multi-family real estate. You will find plenty of two flats and three flats in Jefferson Park and a few hidden four flats. It is best to work with an agent familiar with the neighborhood to find the right investment for you.

Jefferson Park Multi-Family Home Prices

Prices for multi-family homes in Jefferson Park in the last 10 years have increased approximately 55%. In 2010 the average price was approximately $252,000 and in 2020 the average price was about $392,000.

Jefferson Park Multifamily Home Prices

Your Jefferson Park Multi-family Property Experts

Chicago real estate source brokers have the expertise to help you negotiate a successful sale or purchase of your multi-family home. If you’re looking for a Jefferson Park real estate broker to help you achieve your goals, call or text us today 312-788-7079 or contact us to schedule a private consultation.

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