Jefferson Park, Chicago IL · Curated MLS Search

Multi-Family Homes in Jefferson Park, Chicago IL

An editorially curated view of every active multi-family homes listing in Jefferson Park, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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Jefferson Park Market — Multi-Family Homes Comparison

Live MLS data — Jefferson Park vs. Multi-Family Homes

Jefferson Park

Multi-Family Homes

inventory

Active Listings

Sold (Past 6 Mo.)

205

Under Contract

pricing

Avg. List Price

$739,061

$639,982 ↓ 13%

Cost / Sq. Ft.

$278

—

typical home

Living Area

2,039 ft²

—

Avg. Beds

3.9

5.2 ↑ 34%

Avg. Baths

2.7

3.0 ↑ 12%

Days on Market

152

27 ↓ 82%

Multi-Family Homes in Jefferson Park: Market Data

Data as of October 20, 2026 (MLS snapshot; listings below update live)

Chicago Real Estate Source's review of MLS data as of October 20, 2026 shows 17 active listings for Jefferson Park multi-family homes. That is about 24% of the 70 active listings in Jefferson Park across every property type. At the time, 10 more were pending, and 32 sold in the past six months, roughly 5 a month. That works out to about 3.2 months of supply, a level generally read as a seller's market. The median list price was $585,000. That price was $15,000 above the $570,000 median for all active listings in Jefferson Park, across every property type. The average listing had 5.2 bedrooms and 3.0 bathrooms. Listings had been on the market an average of 27 days. If you're buying, it pays to be ready when a new listing comes up. If you're selling, well-priced homes have been moving quickly.

Multi-Family Homes in Jefferson Park, Chicago IL, October 20, 2026
Measure	Value
Active listings	17
All active listings in Jefferson Park, every property type	70
Under contract	10
Sold, past six months	32
Months of supply	3.2
Median list price	$585,000
Median list price, all Jefferson Park listings	$570,000
Average days on market	27

Multi-Family Homes in other neighborhoods

Chicago: 850 active, median $449,950
Cicero: 36 active, median $419,000
Logan Square: 29 active, median $825,000
Belmont Cragin: 17 active, median $499,000
West Ridge: 16 active, median $780,450

Market questions

How many Jefferson Park multi-family homes are for sale?

There were 17 Jefferson Park multi-family homes for sale as of October 20, 2026, based on Chicago Real Estate Source's review of MLS data.

What do Jefferson Park multi-family homes typically list for?

The median list price of Jefferson Park multi-family homes was $585,000 as of October 20, 2026.

How long have Jefferson Park multi-family homes been on the market?

Listings for Jefferson Park multi-family homes had been on the market an average of 27 days as of October 20, 2026.

How do Jefferson Park multi-family homes compare with other neighborhoods?

As of October 20, 2026, there were 17 Jefferson Park multi-family homes for sale. In the same search, Chicago had 850 multi-family homes for sale at a median list price of $449,950, Cicero had 36 multi-family homes for sale at a median list price of $419,000 and Logan Square had 29 multi-family homes for sale at a median list price of $825,000.

Are Jefferson Park multi-family homes priced above or below the Jefferson Park median?

The median list price of Jefferson Park multi-family homes, $585,000, was $15,000 above the $570,000 median for all active listings in Jefferson Park, across every property type.

Is the market for Jefferson Park multi-family homes a buyer's or a seller's market?

With 17 active listings and roughly 5 sales a month, supply of Jefferson Park multi-family homes stood at about 3.2 months, which is generally considered a seller's market.

How many Jefferson Park multi-family homes sold in the past six months?

32 Jefferson Park multi-family homes sold in the six months before October 20, 2026, roughly 5 a month.

Listing data courtesy of Midwest Real Estate Data LLC.

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View All Jefferson Park Chicago IL Multi-Family Homes Listings

$579,000

4 Beds ⋅ 3 Baths ⋅ 12793590 MLS ⋅ NEW 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

$449,900

4 Beds ⋅ 2 Baths ⋅ 12791701 MLS ⋅ NEW Status

Classic brick architecture and timeless character define this Chicago two-unit property, offering an appealing opportunity for homeowners and investors alike. The spacious interiors feature generous living areas, large windows that welcome natural light, and original wood trim that adds warmth and charm throughout. Both units offer functional kitchens with ample cabinetry, comfortable bedrooms, and flexible living spaces ready for personal touches. The upper-level unit features distinctive ceiling lines and inviting rooms, while the full basement provides additional storage and possibilities for future use. A detached two-car garage adds everyday convenience. With its traditional architectural details and versatile layout, this property offers excellent potential for those looking to customize or invest. Conveniently located in the Jefferson Park area near neighborhood parks, shopping, dining, schools, public transportation, and major roadways, with access to Metra and CTA connections throughout Chicago and surrounding communities.

4825 N Meade Avenue, Chicago

$579,000

4 Beds ⋅ 3 Baths ⋅ 12791975 MLS ⋅ PRICE CHANGE 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, good 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

$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

$540,000

6 Beds ⋅ 3 Baths ⋅ 12788881 MLS ⋅ ACTIVE Status

Beautifully maintained building in the desirable Jefferson Park/Gladstone Park area! Each floor features 2 bedrooms and one bathroom. The finished basement offers additional living space with an in-law arrangement, including two bedrooms and a full bathroom. The property is tenant-occupied, but easy to show. All tenants are on month-to-month leases, offering flexibility for investors or owner-occupants.

5618 N Major Avenue, Chicago

$519,900

4 Beds ⋅ 2 Baths ⋅ 12664739 MLS ⋅ CONTINGENT Status

Fantastic 2 Flat that only needs some personal touches. Tenant in place on 2nd Fl. is month to month. Long time owner occupies 1st floor. The basement is fully unfinished. 2 Furnaces, water tanks, electrical boxes (100 amp) and gas meters. First floor has 3 bedrooms, HWFL's in 2 bedrooms, Living room, and Dining room! Stainless steel appliances! Dining room has crown molding. There is a spacious deck and 2 car garage! The 2nd floor has 1 bedroom and 1 bath with a large walk in closet, enclosed porch. Separate entrances! The Brickwork is in great condition. Flood control!!

5349 W Winona Street, 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

$769,000

8 Beds ⋅ 5 Baths ⋅ 12777301 MLS ⋅ ACTIVE Status

Updated legal 2-flat in Jefferson Park with a finished English Garden Unit. Both legal units feature 3 bedrooms, 1.5 baths, spacious layouts with separate dining areas and additional kitchen dining space, recessed lighting, and updated kitchens with quartz countertops, stainless steel appliances, and ample cabinetry. Unit 1 is leased for $2,650/month and Unit 2 for $2,400/month, generating $5,050/month or $60,600 annually. Unit 1 rent includes electricity, gas/heat, water, trash, landscaping, and one garage parking space. Unit 2 rent includes electricity and water. The finished basement is currently vacant and offers 2 bedrooms and 1 full bath, with estimated rental potential of approximately $2,300/month, subject to applicable laws, zoning, approvals, and permitted use. If legally approved for rental use, potential gross income could reach approximately $7,250/month or $87,000 annually. 2024-2025 improvements include a new roof and windows, updated kitchens and bathrooms, tuckpointing, and improvements to the garage-top deck. Additional features include rear decks, shared outdoor space, and coin-operated laundry. Conveniently located near shopping, dining, transportation, parks, and neighborhood amenities. Excellent opportunity for an investor, owner-occupant, or multi-generational household.

5759 N Elston Avenue, Chicago

$720,000

6 Beds ⋅ 4 Baths ⋅ 12750828 MLS ⋅ CLOSED Status

Chicago

$599,900

6 Beds ⋅ 4 Baths ⋅ 12776463 MLS ⋅ CONTINGENT Status

Prime Jefferson Park location walking distance to Jefferson Park and Metra train station on Milwaukee near Lawrence. Beaubien grammar school and Robert's Square a short couple block walk. Beautiful large 2.5 story 2 flat with additional non-conforming basement apartment plus room to expand up in large open attic with high ceilings. All bright spacious apartments have lovely, updated cabinet kitchens with stoves, refrigerators, dishwashers and microwaves. Nicely updated tile baths. Hardwood floors throughout, updated electric, separate gas hot water heat. First floor offers 6 large rooms 3 bedrooms and 2 full baths. Long term tenants that are friends of owners are both on a month-to-month rental. Rents should be much higher. First floor easily $2300. second floor $2000. Garden unit is currently vacant but valued at $1500. Oversize corner lot with a 2+ car garage that faces the street for easy access, additional income and additional off-street parking. Newer privacy fence surrounds a lovely yard. Potential income with garage $6200 per month or $74,400. annually. Any questions about this listing please contact Norbert Mika. Text or email preferred.

5059 W Argyle Street, Chicago

$740,000

6 Beds ⋅ 3 Baths ⋅ 12776241 MLS ⋅ ACTIVE Status

LARGE 2 FLAT BRICK WITH 3 BEDROOM APARTMENTS, SEMI FINISHED BASEMENT WITH FRONT ENTRANCE. HARDWOOD FLOORS THROUGHOUT, GREAT INVESTMENT OR OWNER-OCCUPIED HOME.

5236 W Montrose Avenue, Chicago

$569,999

4 Beds ⋅ 3 Baths ⋅ 12775522 MLS ⋅ CONTINGENT 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. Unit 1 is empty perfect for owner occupancy, making rental income, ready now for you to move in. 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 available for owner occupancy now. 2nd floor unit lease ends 12/1. Do not miss this chance to live and have others cover your mortgage!

5037 W Winona Street, Chicago

$1,195,000

9 Beds ⋅ 6 Baths ⋅ 12775394 MLS ⋅ ACTIVE Status

Old Irving/Portage Park! Fully Remodeled three unit! This ideal Owner-Occupier is offering three spacious 3-bedroom, 2-bathroom apartments! The stylish kitchens feature sleek quartz countertops, a full-height backsplash, and a stainless steel appliance package including a dishwasher and microwave. Spacious bedrooms comfortably accommodate queen- or king-size furniture, while two beautifully updated bathrooms feature modern finishes and spa-inspired walk-in showers. Bonus updates include recessed lighting, New windows, new water heaters, new boiler, modern light fixtures, and numerous additional updates throughout the building. Residents have access to free laundry in the basement, a shared patio, and plenty of space to make themself at home. Ideally located near Portage Park's beautiful parks, neighborhood shops, restaurants, cafes, and public transportation, this apartment offers the perfect blend of modern updates, space, and convenience. Two car garage.

5338 W Montrose Avenue, Chicago

$670,000

4 Beds ⋅ 2 Baths ⋅ 12600798 MLS ⋅ ACTIVE Status

Welcome to this Lovingly Maintained Gladstone Park Gem! Owned and cherished by the same owner-occupant for over 20 years, this two-flat at 5426 N Lovejoy shines with true pride of ownership and consistent, thoughtful updates throughout. Featuring two units with 2 bedrooms and 1 bathroom, and an additional 1 bedroom, 1 bathroom unit (non conforming) in the basement, it's the perfect opportunity for an investor or an owner-occupant seeking a move-in-ready home with built-in income. You'll be greeted by a gorgeous front porch, the perfect spot for your morning coffee. Both the first and second floors offer 2 bedrooms and 1 bathroom with bright, functional layouts. The first-floor unit includes a versatile bonus space, ideal as an office, sitting room, or additional sleeping area, along with a charming wood-burning fireplace. The finished basement features a 1-bedroom, 1-bathroom in-law suite (non-conforming), offering excellent flexibility for extended family. Enjoy immediate cash flow, with the first floor recently renting for $2,160/month (currently owner-occupied) and the second floor at $1,975/month. This building has been lovingly maintained with numerous mechanical updates over the years, including new electric and copper plumbing throughout all three units. Units 1 and 2 feature updated can lighting in the kitchens, with Unit 2 also updated in the dining area. The first- and second-floor hardwood floors have both been recently refinished. Additional conveniences include shared basement laundry for all occupants and a sump pump/flood control system for added peace of mind during rainy months. Located in a quiet, tree-lined section of the neighborhood, you're just minutes from the Blue Line, Metra, and I-90/94 - a true commuter's dream. Don't miss this rare find, where long-term pride of ownership meets modern rental demand!

5426 N Lovejoy Avenue, Chicago

$550,000

5 Beds ⋅ 3 Baths ⋅ 12773644 MLS ⋅ PENDING Status

Well situated two flat home spanning 2 lots in the Jefferson Park side of Portage Park Chicago. What a yard! Fully fenced, 6250 sq ft lot with a dreamy yard, 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! The 2 unit has a partially finished basement with a bedroom/bar setup and full bath. The attic is unfinished and holds the second floor's central heat and air. The second floor 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 and high ceilings. This unit is in need of some TLC. Unit 1 and garden are vacant and ready for new life while 2nd floor's lease ends Feb. 28th 2027. Keep as an income generating property or convert to the most beautiful single family home around! Great location by greenspace, walk to the Metra, bus and Jeff Park Blue line transit center and just 2 blocks from Jewel, Starbucks, Prussing Elementary, great Filipino and Polish restaurants.. ALL within a 5 minute walk...

5753 W Giddings Street, Chicago

$599,000

5 Beds ⋅ 3 Baths ⋅ 12772229 MLS ⋅ ACTIVE Status

4542 N Long Avenue, Chicago

$570,000

5 Beds ⋅ 3 Baths ⋅ 12769997 MLS ⋅ ACTIVE Status

3 Total Dwelling Units Multi-Family building (legal 3 Flat with zoning RS-3 on recently issued Zoning Certificate attached in Add'l 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

$755,000

7 Beds ⋅ 3 Baths ⋅ 12764380 MLS ⋅ CONTINGENT Status

Rare opportunity to own a fully renovated, income-producing 2-flat in the heart of Jefferson Park! Offering more than 3,000 square feet of living space and impressive rental income, this turnkey property is ideal for investors or owner-occupants looking to supplement housing costs with rental income. Unit 1 is currently rented for $3,200/month, while the beautifully remodeled second-floor unit offers projected rental potential of approximately $2,900/month, bringing total pro forma rental income to approximately $6,100/month or $73,200 annually. Each unit features three bedrooms, one full bath, abundant natural light, and separate utilities including Central Air. The first-floor unit offers hardwood floors, a generous living and dining space, and a spacious kitchen with white cabinetry, stainless steel appliances, granite countertops, and an oversized island with seating for four. The second-floor unit was remodeled just this year and features luxury vinyl flooring, a gorgeous new kitchen with white cabinetry, quartz countertops and new stainless steel appliances, plus its own in-unit washer and dryer and updated bathroom. Finally, the finished lower level with a washer / dryer, large family room, additional non-conforming bedroom and full bath provides exceptional additional living space. 3 floors and 3 bathrooms - one on each level! Major property improvements include a newer roof, drain tile and sump pump. Outside, enjoy a fully paved, low-maintenance backyard, two-car garage, and additional parking pad. Conveniently located near the Jefferson Park Blue Line and Metra stations, I-90/94, O'Hare, schools, parks, shopping and restaurants. With substantial current and projected rental income, extensive recent improvements, separate utilities, and excellent long-term potential, this is a truly turnkey opportunity in one of Chicago's most desirable Northwest Side neighborhoods.

5351 W Foster Avenue, Chicago

$635,000

4 Beds ⋅ 3 Baths ⋅ 12762156 MLS ⋅ CLOSED Status

Rare opportunity to own a well-maintained legal 2-flat situated on an oversized 43' x 125' lot in the Jefferson Park/Portage Park area. The property features two spacious units, each with 2 bedrooms and 1 full bath, offering flexibility for owner-occupancy, extended family, or investment. A full basement provides additional finished space, including a full bathroom, an additional room, and a kitchenette area. Numerous improvements include newer windows and doors, updated kitchens, and a newer 2.5-car detached garage. The oversized lot provides excellent outdoor space and is a standout feature for the area. Conveniently located near transportation, shopping, restaurants, parks, and neighborhood amenities.

5849 W Wilson Avenue, Chicago

$550,000

6 Beds ⋅ 2 Baths ⋅ 12753893 MLS ⋅ ACTIVE Status

Great opportunity to own 2-unit property located in Chicago's Portage Park neighborhood minutes from Jefferson Park and Mayfair. Both units are currently occupied with leases in place through May 2027. Tenants pay electric and gas. Interiors feature vintage character, including woodwork and built-in hutches, with spacious kitchens and formal dining rooms. The property also includes enclosed back porch, unfinished basement with storage and laundry space, unfinished attic, and a detached two-car garage. Conveniently located less than a mile from two CTA Blue Line stations and the Jefferson Park Metra station, with easy access to I-90 and Milwaukee Avenue, shopping, dining, parks, and other neighborhood amenities.

5102 W Sunnyside Avenue, Chicago

$624,900

4 Beds ⋅ 3 Baths ⋅ 12746405 MLS ⋅ CONTINGENT 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

$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

$584,999

4 Beds ⋅ 2 Baths ⋅ 12751624 MLS ⋅ PRICE CHANGE 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

$540,000

4 Beds ⋅ 2 Baths ⋅ 12733038 MLS ⋅ CLOSED 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

$700,000

6 Beds ⋅ 3 Baths ⋅ 12565108 MLS ⋅ CLOSED 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

$535,000

4 Beds ⋅ 3 Baths ⋅ 12743877 MLS ⋅ CLOSED 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

$650,000

6 Beds ⋅ 4 Baths ⋅ 12736543 MLS ⋅ CLOSED Status

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

$565,000

5 Beds ⋅ 3 Baths ⋅ 12736554 MLS ⋅ CLOSED 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

$300,000

3 Beds ⋅ 2 Baths ⋅ 12715449 MLS ⋅ CLOSED 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

$475,000

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

$349,900

4 Beds ⋅ 3 Baths ⋅ 12693972 MLS ⋅ ACTIVE 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

$625,000

6 Beds ⋅ 2 Baths ⋅ 12657416 MLS ⋅ CLOSED 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

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