Jefferson Park Real Estate

Located in the vibrant city of Chicago, Jefferson Park is a neighborhood that offers a perfect blend of suburban tranquility and urban convenience. Situated in Cook County, Illinois, this charming community is known for its tree-lined streets, picturesque parks, and close-knit atmosphere.

One of the standout features of Jefferson Park is its excellent transportation options. The neighborhood is conveniently located near major highways, making it easy for residents to commute to downtown Chicago or other parts of the city. Additionally, the Jefferson Park Transit Center provides access to multiple bus routes, the CTA Blue Line, and the Metra Union Pacific Northwest Line, ensuring that residents have plenty of options for getting around.

In terms of amenities, Jefferson Park has something for everyone. The neighborhood is home to a variety of shops, restaurants, and entertainment venues, offering residents plenty of opportunities for shopping, dining, and leisure activities. The Jefferson Park Sunday Market is a popular attraction, where locals can browse through a wide range of fresh produce, handmade crafts, and artisanal goods.

Nature enthusiasts will appreciate the abundance of green spaces in Jefferson Park. The neighborhood is home to several parks, including the expansive Jefferson Memorial Park, which features sports fields, a swimming pool, and a golf course. These parks provide residents with ample opportunities for outdoor recreation and relaxation.

With its convenient location, charming atmosphere, and array of amenities, Jefferson Park is an ideal neighborhood for those seeking a balance between city living and suburban tranquility. Whether you're looking for a peaceful community or easy access to the bustling city, Jefferson Park has it all.

Newest Listings in Jefferson Park

$389,000

3 Beds ⋅ 2 Baths ⋅ 12715449 MLS ⋅ NEW 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

$299,000

12715345 MLS ⋅ NEW Status

Rare Jefferson Park Pocket lot opportunity on one of the area's most desirable blocks. This 25 x 125 parcel features approximately 3,125 sq. ft. of land, a curb-cut driveway, and a 2-car garage with party door already on site. The existing driveway and garage create immediate flexibility for parking, storage, a work vehicle, hobby use, or possible boat/trailer storage. Adjacent 2-flat at 4846 W. Gunnison is also available for sale, creating a unique opportunity to purchase one or both properties. Set directly across from a beautifully updated Chicago Park District park, the 4800 block of Gunnison has the feel of a quiet residential pocket with green space right at your doorstep. Close to the Blue Line, Metra, parks, shopping, restaurants, and neighborhood conveniences, with easy access to I-90 and I-94. Property is being sold as-is.

4844 W Gunnison Street, Chicago

$639,900

6 Beds ⋅ 2 Baths ⋅ 12714843 MLS ⋅ NEW Status

Fully renovated and leased with great tenants! Instant profit with above market rents, or occupy one unit yourself. Legal 2-flat featuring 3 bedroom 1 bath units. 2 car garage. Central Air, separate furnaces. Common area laundry. Quiet street in Forest Glen neighborhood. Nothing to do but collect the rent... Total rents 4975. Non-conforming unoccupied 1Bed unit in basement is vacant. In great shape but being offered AS IS.

4854 W Winnemac Avenue, Chicago

$1,395,000

12714988 MLS ⋅ NEW Status

For sale: 23,000 SF industrial building with two drive-in doors on a 26,000 SF site. Excellent North Chicago location with immediate access to I-90, the Gladstone Park UP-NW Metra Station, O'Hare International Airport, and the Northwest suburbs. M1-2 zoning. Ideal for manufacturing, distribution, logistics, warehousing, and other industrial uses.

5504 N Northwest Highway, Chicago

$579,999

4 Beds ⋅ 3 Baths ⋅ 12714777 MLS ⋅ NEW 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.

5037 W Winona Street, Chicago

$569,999

2 Beds ⋅ 2 Baths ⋅ 12713331 MLS ⋅ NEW Status

Welcome to this beautifully remodeled home, perfectly situated on an oversized lot in the highly desirable Jefferson Park neighborhood. This move-in-ready residence has been completely renovated with quality craftsmanship and modern finishes throughout. The main level features a spacious and inviting layout, including a stunning European-style kitchen with sleek cabinetry, premium finishes, and contemporary design. You'll also find generously sized bedrooms and a beautifully updated full bathroom, providing both comfort and functionality. The finished basement offers exceptional flexibility with a second kitchen, an additional bedroom, a full bathroom, and a separate exterior entrance, making it ideal for an in-law arrangement, extended family living, or potential rental income. The attic presents an incredible opportunity to add even more living space. Water hookups are already installed, allowing for an easy conversion into additional bedrooms and a full bathroom, a luxurious primary suite, or a private guest retreat. Situated on an oversized lot, the property offers plenty of outdoor space for entertaining, gardening, or future improvements. The backyard is a gardener's delight, featuring an abundance of mature red and white currant bushes along with gooseberry bushes, providing both beauty and a delicious seasonal harvest. Conveniently located near parks, schools, shopping, restaurants, and public transportation, this exceptional home combines modern style, versatile living space, and endless possibilities. Don't miss this rare opportunity to own a fully remodeled home with income potential and room to grow!

4833 N Moody Avenue, Chicago

$485,000

3 Beds ⋅ 3 Baths ⋅ 12713873 MLS ⋅ NEW Status

RARE COMMODITY OF TREX COVERED FRONT PORCH AND REAR DECK IN ONE HOME!! Great value and location is waiting for you in this south-facing, updated and long loved English with a front covered porch, sitting on a 30 foot-wide lot, in the heart of the highly coveted Jefferson Park. As soon as you enter you are welcomed by a large, sun-drenched living room with bay windows. Main level also includes a large dining room, fully equipped and updated kitchen with Stainless-Steel Appliances, one good sized guest bedroom and a full bathroom. Updates on the main level include freshly painted walls (06/2026), resurfaced hardwood floors (06/2026), new kitchen countertops (2026) and new carpet in the guest bedroom (2026). Upper level brings the master bedroom as well as a secondary bedroom and a half bath. Updates on upper level include newer windows, new carpet (2026) as well as freshly painted walls (06/2026). Full updated basement includes updated full bathroom (2021), newer laminate flooring (2021), new carpet on the stairs (2026) as well as fresh paint (06/2026). Fully equipped laundry room also included in the basement. Other updates include; New Roof (2015), New Hot Water Heater (2014), Freshly painted rear deck (2025), new garage door (06/2026), all gutters were cleaned (06/2026), full exterior pressure wash (06/2026) and new backyard grass (06/2026). All these updates provide confidence and security for years to come. **PRIME JEFFERSON PARK LOCATION** Easy access to I-90 and I-94 as well as the Jefferson Park CTA and METRA make it a great choice for commuters. Less than a mile away from the highly rated Prussing Elementary, 1.5 miles from Taft High School as well as from Wilbur Wright College. Easy Access to Harlem Irving Plaza, Harwood Heights, Norwood Park as well as Ridgemoor Country Club. Do not miss out.

4953 N Meade Avenue, Chicago

$525,000

6 Beds ⋅ 4 Baths ⋅ 12703033 MLS ⋅ NEW 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

$665,000

5 Beds ⋅ 3 Baths ⋅ 12707341 MLS ⋅ NEW Status

This Jefferson Park Tudor checks the boxes! Its massive main level floor plan provides dedicated living and dining rooms, an open layout kitchen with an adjacent family room and deck, and still yet a main level bedroom and bathroom. The hardwood floors, stylish wainscoting, and plentiful kitchen cabinet storage certainly don't hurt either. Upstairs provides 4 bedrooms itself, and the finished basement has more than enough space for a large rec room, a gym, or many other configurations to suit your needs. Commuters will appreciate the options - either a quick drive to I90 and I94, or the home is also under a half mile to the Forest Glen Metra station. Even closer is Marianos to pick up groceries on the way home. Cyclists will appreciate the access to virtually unlimited trails through forest preserves just a few blocks away. All this with solid schools (Farnsworth Elementary and Taft HS) and on a quiet block with a pleasant tree canopy.

5310 N Lockwood 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

$598,600

3 Beds ⋅ 3 Baths ⋅ 12711139 MLS ⋅ ACTIVE Status

Beautifully renovated home located in the desirable Forest Glen neighborhood, featuring an open-concept layout perfect for modern living and entertaining! This spacious property offers 3 bedrooms and 3 full bathrooms, plus an additional bedroom in the basement ideal for guests, a home office, or extra living space. The stunning kitchen showcases brand-new cabinets, gorgeous quartz countertops, and plenty of space to cook and gather. Enjoy the convenience of a 2-car garage and an excellent location just 2 blocks from the highway, making commuting easy. The home is also only 5 minutes from the Metra station and close to shopping, restaurants, parks, and everyday amenities. With stylish updates, functional space, and a prime location this move-in ready home is a fantastic opportunity you do not want to miss!

4829 W Strong Street, Chicago

$869,900

4 Beds ⋅ 4 Baths ⋅ 12710673 MLS ⋅ ACTIVE Status

Discover this stunning, Feng Shui-inspired 5-bedroom, 4-bath bungalow in the heart of sought-after Jefferson Park. Completely renovated from top to bottom, this exceptional home offers over 3,000 square feet of beautifully finished living space on an oversized 30-foot-wide lot. Every detail has been thoughtfully designed, blending timeless character with today's modern style and comfort. The open-concept main level features a chef's kitchen with quartz countertops, a large island, soft-close cabinetry, premium stainless steel appliances, and a spacious dining area perfect for entertaining. Two elegant electric fireplaces and engineered wire-brushed oak hardwood flooring throughout all three finished levels create a warm, sophisticated feel. For added convenience, the main level includes a spacious bedroom and a full bath, while the second floor features a private primary suite, creating an ideal layout for guests, multigenerational living, or flexible family needs. Enjoy peace of mind with dual-zone energy-efficient HVAC, new windows, a tankless water heater, a new furnace, an ejector pump, new tuckpointing, and a roof approximately three years old. The finished lower level offers high ceilings, a private exterior entrance, an additional bedroom, and a full bath-perfect for related living, guests, a home office, or recreation. Additional highlights include two mudrooms and a separate, spacious laundry area, providing exceptional functionality, organization, and convenience for everyday living. Step outside to a fully fenced backyard with plenty of green space and a 2.5-car garage. Conveniently located near Prussing Elementary School, Portage Park, shopping, restaurants, the Blue Line, Metra, and I-90/94, this move-in-ready home combines luxury finishes, quality craftsmanship, and an unbeatable location.

5748 W Eastwood Avenue, Chicago

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