Jefferson Park Homes under $750,000

Welcome to Jefferson Park, a vibrant neighborhood nestled in the heart of Chicago, Illinois. Known for its family-friendly atmosphere and strong sense of community, Jefferson Park offers a perfect blend of urban convenience and suburban charm. With tree-lined streets, well-maintained parks, and a rich history, this neighborhood is a hidden gem for those seeking a welcoming place to call home.

Jefferson Park boasts a diverse array of homes, including charming bungalows, modern townhouses, and spacious single-family residences—all available for under $750,000. This makes it an ideal location for first-time homebuyers, growing families, and anyone looking to invest in a dynamic community without breaking the bank. The homes here often feature unique architectural details, generous yards, and easy access to public transportation, making commuting a breeze.

In addition to its attractive housing options, Jefferson Park is known for its excellent schools, local shops, and a variety of dining experiences. Residents enjoy access to beautiful parks such as Jefferson Park itself, where families can gather for picnics, sports, and community events throughout the year. The neighborhood is also well-connected to downtown Chicago, making it easy to enjoy the city's vibrant culture while returning to the tranquility of home.

If you're searching for a neighborhood that combines affordability, community spirit, and a welcoming environment, look no further than Jefferson Park. Discover your dream home in this charming Chicago enclave today!

Newest Jefferson Park Homes under $750,000

$255,000

2 Beds ⋅ 2 Baths ⋅ 12776882 MLS ⋅ NEW Status

An affordable entry point into homeownership with room to make it your own. This charming 2 bed 2 bath home offers first-time buyers the chance to own now, update over time, and build equity along the way, while also appealing to investors looking for a value-add opportunity. The home offers a manageable footprint and a straightforward layout that provides a solid starting point for future improvements. A one-car detached garage adds everyday convenience, while the surrounding neighborhood offers the residential feel many buyers are looking for, with tree-lined streets, parks, local businesses, and easy access to the rest of the city. Move in and improve it at your own pace, or take on the renovation from the start. Either way, this is an opportunity to create a home that reflects your style while adding value over time.

4562 N Mulligan, Chicago

$630,000

4 Beds ⋅ 4 Baths ⋅ 12778327 MLS ⋅ NEW Status

This is your chance to own one of the most beautiful houses on the NW side on a block that hosts block parties, October Fests, Easter egg hunts, holiday parties, and more! Full of character and natural light, this home features beautiful hardwood floors, fresh paint, and a huge primary suite with a walk-in closet, and beautifully renovated private bathroom. The kitchen has been updated and flows seamlessly into a dining area that could one day be part of an even larger kitchen. The finished basement has a wet bar, fully renovated bathroom, and flex space. Major updates include a new roof and front porch in 2023, furnace in 2021, AC in 2024, water heater in 2021, dishwasher in 2026, and garbage disposal in 2023.

6051 N Marmora Avenue, Chicago

$679,000

3 Beds ⋅ 3 Baths ⋅ 12775474 MLS ⋅ NEW Status

4903 N Moody Avenue, Chicago

$599,900

6 Beds ⋅ 4 Baths ⋅ 12776463 MLS ⋅ NEW 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 ⋅ NEW 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 ⋅ 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. 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 availabe for owner occupancy now. Do not miss this chance to live and have others cover your mortage!

5037 W Winona Street, Chicago

$589,000

6 Beds ⋅ 3 Baths ⋅ 12775298 MLS ⋅ RE-ACTIVATED Status

Excellent opportunity to own this well-maintained brick 2-flat with a non-conforming 3rd unit in the basement. All 3 units have 2 bedrooms & 1 bath! This property offers spacious layouts, quality updates, & excellent income potential! Special unit feature include: Hardwood floors & a spacious deck overlooking the yard on the 1st floor & hardwood floors, a walk-in pantry, and an enclosed porch on the 2nd floor. Additionally there are thermopane windows throughout, a nice fully fenced yard, and a large 2 & 1/2-car garage with room for lawn equipment & a workbench. Front hallway freshly painted! Entire 1st floor and basement apartments painted last summer. Major improvements include a roof 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

5630 W Goodman Street Unit #301, Chicago

$289,500

2 Beds ⋅ 2 Baths ⋅ 12774389 MLS ⋅ ACTIVE Status

Beautifully remodeled, move-in-ready 2-bedroom, 2-bathroom top-floor condo in a convenient Jefferson Park location. This home features freshly painted walls, a remodeled kitchen with new appliances, remodeled bathrooms, refinished floors and newer laminate flooring in the bedrooms. Enjoy a lovely private balcony with space to relax outdoors. Building constructed in 2005. Walk to Jefferson Park and the Jefferson Park Transit Center for Blue Line, Metra and bus connections. Easy access to the Kennedy Expressway, with nearby shopping, coffee and dining. Rear tandem parking may accommodate up to three vehicles, depending on size. A beautiful place to call home with everyday conveniences close by.

5630 W Goodman Street Unit #301, Chicago

$670,000

5 Beds ⋅ 3 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. 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 ⋅ ACTIVE 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

$470,000

3 Beds ⋅ 3 Baths ⋅ 12771633 MLS ⋅ ACTIVE Status

Welcome home to this wonderful Queen Anne brick bungalow in Chicago's desirable Jefferson Park neighborhood. Offering 5 bedrooms, 3 full baths, and a 3-car garage, this spacious home provides flexible living space for a variety of needs. The main level features beautiful hardwood floors, a welcoming living room, formal dining room, one bedroom, and a remodeled kitchen with granite countertops and stainless steel appliances. The second floor offers 2 additional bedrooms. The finished basement includes 2 more bedrooms, a second full kitchen, laundry area, and excellent potential for an in-law arrangement, extended-family living, or additional recreational space. Additional highlights include a newer gas forced-air furnace, newer central air-conditioning condenser, a newer wood deck, and a generous 3-car garage. The location is hard to beat-just two blocks from Metra, with convenient access to I-90 and I-94, and only minutes from O'Hare Airport and Rosemont. Enjoy the convenience of city living with easy access to everything Chicago and the surrounding suburbs have to offer.

5650 N Mason Avenue, Chicago

$242,000

2 Beds ⋅ 1 Baths ⋅ 12773464 MLS ⋅ ACTIVE Status

5312 W Windsor Avenue Unit #2W, Chicago

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