Oak Park Homes under $500,000

Oak Park Homes under $500,000

Welcome to Oak Park, Illinois—a vibrant community that seamlessly blends history, culture, and modern living. Located in Cook County and just a stone's throw from downtown Chicago, Oak Park is renowned for its stunning architecture, including the iconic designs of Frank Lloyd Wright. This charming neighborhood is not only rich in artistic heritage but also offers a warm, welcoming atmosphere that makes it an ideal place to call home.

For those looking to settle in this picturesque suburb without breaking the bank, Oak Park boasts a variety of homes priced under $500,000. Here, you can find an array of options, from beautifully restored vintage bungalows to contemporary condos. Each property tells its own story, often featuring unique architectural details that reflect the area’s historical significance.

Living in Oak Park means enjoying a community that values education, with top-rated schools and a plethora of parks and recreational spaces. Stroll through the tree-lined streets, visit the local farmers' market, or indulge in one of the many artisanal cafes and restaurants that dot the area.

Convenient public transportation options make commuting to Chicago a breeze, allowing residents to enjoy the best of both worlds—a suburban lifestyle with easy access to the bustling city.

Whether you're a first-time homebuyer or looking to downsize, Oak Park's diverse real estate market has something for everyone. Discover your dream home in this enchanting neighborhood where history meets modern convenience!

Newest Oak Park Homes under $500,000

839 Madison Street Unit #503, Oak Park
$466,700
2 Beds ⋅ 1 Baths ⋅ 12775697 MLS ⋅ NEW Status
Welcome to Oak Park Commons! Become an owner in the first cohousing community in Illinois. Owners enjoy the best of both worlds: ownership of individual condo units and shared common spaces that foster social interaction among residents. This light-filled 2 bedroom/1 bath unit has a modern floor plan designed for today's living. The open concept living room and kitchen have gleaming hardwood floors and open to a private balcony. The kitchen boasts 42" cabinets, quartz countertops, island with breakfast bar, designer fixtures and lighting, and stainless steel appliances. The bathroom has a tub/shower, custom mirrors with designer lighting, and an undermount vanity sink with quartz countertops. The bedrooms are separated by living space for added privacy. Enjoy quiet and comfortable living with a truss joist silent floor system, advanced sound attenuation between units and floors, high efficiency low e windows and balcony doors, and high efficiency split system a/c with heat pump. This unit is equipped with a home network connection for home entertainment and CAT 5 Rg interface. All of this plus in-unit laundry. Common rooms on the fifth floor include a large room designed for dining, celebrations, and social events. The common great room includes a kitchen with two stoves, several sinks, a pantry and multi-level counter space for ease of access. There is a fireplace alcove and large windowed doors that open to the terrace and adjoining roof garden. Other common rooms include the quiet room with workspace and common Wi-Fi, meeting rooms that can facilitate small group gatherings, an exercise room, and a guest suite to provide overflow space for visitors. All of this in a sustainable building with National Green Building Standard "Silver" certification with an advanced high-efficiency hot water system and electric car charging stations in the covered garage. State-of-the-art intercom and security systems. In addition, this building is fully accessible. Conveniently located near parks, schools, and Downtown Oak Park. A great location for commuters! Just two stops to downtown's Ogilvie Transportation Center via Metra UP West line. Enjoy easy access to the CTA Blue and Green Lines and Madison Street buses; biking is a breeze with many tree-lined side streets and the Madison Street bike line that runs right past the Commons. NOTE: Unit photos are from similar rooms in other units.

839 Madison Street Unit #503, Oak Park
1130 Washington Boulevard Unit #3A, Oak Park
$375,000
3 Beds ⋅ 2 Baths ⋅ 12753342 MLS ⋅ NEW Status ⋅ Lions Gate Condominiums BLDG.
Top-floor, end-unit 3-bedroom, 2-bath vintage condo in Lions Gate Condominiums, a 1925 brick courtyard building on Washington Blvd in Oak Park, IL. Come home through a landscaped courtyard of brick walkways and garden benches, then enter inside to leaded diamond-pane windows, arched doorways, and hardwood floors that carry a century of character. South light pours into the 22x15 living room, made for slow Sunday mornings and evenings with a good book. The separate dining room (14x11) is ready for long dinners with friends. The updated kitchen keeps pace with white shaker cabinetry, granite counters, a breakfast bar, subway tile, a gas range, and stainless steel appliances, with a back door to the rear porch for morning coffee. The primary bedroom (19x13) has two closets; the hall bath offers red marble tile, a soaking tub, and a separate glass-door shower; the third bedroom has its own en-suite bath, perfect for guests or a home office. Central air, in-unit laundry, extra storage, off-street parking for rent, and pets welcome. Minutes to the Green Line, Blue Line, Oak Park Metra, I-290, and downtown Oak Park dining and shops. Vintage soul, modern ease, and a courtyard to come home to in Oak Park.

1130 Washington Boulevard Unit #3A, Oak Park
344 S Maple Avenue Unit #2B, Oak Park
$339,000
3 Beds ⋅ 2 Baths ⋅ 12774636 MLS ⋅ NEW Status ⋅ Lions Gate Condominiums BLDG.
**Corner unit with south and west-facing windows and over 1,400 square feet of living space in Oak Park's Lions Gate Condominiums: a one-level, three-bedroom, two-bathroom residence in a 1925 courtyard building at the corner of Washington Boulevard and Maple Avenue. Windows on two exposures bring in light throughout the day, framed by coved ceilings, original windows, and hardwood floors. Fresh paint, updated lighting fixtures, and custom blinds carry through every room. The kitchen features 42-inch cabinets, granite countertops, a tiled backsplash, and a full suite of new stainless steel appliances - refrigerator, gas range, dishwasher, and microwave - with a breakfast bar for casual dining. Three generously sized bedrooms, each fitted with a custom California Closets system, include a bedroom with an en suite full bath; the hall bath offers a soaking tub alongside a separate shower. A newer in-unit washer and dryer, central air, and gas forced-air heat keep day-to-day living low-maintenance. A shared covered deck with new exterior stairs, a large private storage unit and dedicated bike storage round out the building's amenities. Located close to downtown Oak Park, 2.5 blocks from Mills Park, with close access to the Green Line, Metra, and Blue Line, plus Lake Street's restaurants and shops. I-290 is minutes away for drivers. Lions Gate Condominiums is a well-established Oak Park building with a track record of recent unit sales and renovations, offering vintage architectural character - coved ceilings, hardwood floors, original windows - paired with a fully updated kitchen and baths. A corner exposure, one-level layout, built-in storage throughout, and a low-maintenance monthly assessment make this Oak Park condominium a straightforward move for anyone trading square footage for simplicity without giving up character. You will be moved in just in time for the entrances and inside stairwells to be refeshed and repainted.

344 S Maple Avenue Unit #2B, Oak Park
2 Le Moyne Parkway Unit #2N, Oak Park
$150,000
2 Beds ⋅ 1 Baths ⋅ 12773873 MLS ⋅ NEW Status

2 Le Moyne Parkway Unit #2N, Oak Park
711 Washington Boulevard Unit #2E, Oak Park
$349,900
2 Beds ⋅ 1 Baths ⋅ 12772673 MLS ⋅ NEW Status
Just wow! Incredible art glass, built-ins and hardwood floors throughout! This second floor (approx. 1400 sq ft!) condo in a historically significant 3-story vintage building checks the boxes with a central location close to 3 train lines, shopping & restaurants, connected outdoor living space, in-unit laundry, and garage parking! You will love the art glass, exceptional woodwork and period details including a lovely decorative fireplace in the den/library with pocket doors opening to a spacious living room. Here you will find a reading nook + access to your huge adjacent terrace for enjoying sunny days and dining al fresco! Tall ceilings and gallery walls grace the hallway to 2 nice-size bedrooms and a central bathroom. Next, a sunny, large formal dining room with a built-in buffet and beamed ceiling + access to the large galley kitchen with breakfast bar, in-unit laundry, and a cozy south-facing sun room/office/breakfast room. The back entry leads you to generous basement storage, a shared, peaceful backyard patio and your private, deeded individual garage space. Pet Friendly. Simply Stunning.

711 Washington Boulevard Unit #2E, Oak Park
500 Washington Boulevard Unit #206, Oak Park
$180,000
1 Beds ⋅ 1 Baths ⋅ 12684446 MLS ⋅ NEW Status
**Updated 1-Bedroom Condo in Sought-After Oak Park!** This inviting condo features a spacious bedroom, full bath, comfortable living room, dining area, and an updated kitchen with new cabinets, granite countertops, new sink, and stainless steel appliances. Includes **one assigned parking space**. A great opportunity in a desirable Oak Park location!

500 Washington Boulevard Unit #206, Oak Park
504 S Austin Boulevard Unit #1, Oak Park
$325,000
3 Beds ⋅ 2 Baths ⋅ 12770128 MLS ⋅ NEW Status
Discover a rare opportunity to own a spacious 3-bedroom, 2-bath first-floor condo in a beautiful vintage building in the heart of the Oak Park Arts District. With generous living spaces, high ceilings, beautiful original details, and modern updates, this home blends timeless character with everyday convenience. Step inside to a bright, airy living room featuring soaring ceilings, oversized windows, beautiful hardwood floors, a decorative fireplace mantel, and elegant wall sconces. The spacious front primary bedroom is conveniently located next to a full bath with a separate soaking tub and walk-in shower. A hallway with a cedar closet leads to the large formal dining room. The well-appointed kitchen is designed for both everyday living and entertaining, featuring top-of-the-line stainless-steel appliances, granite countertops, a built-in buffet, and a butler pantry. An inclosed porch containing in-unit laundry adds even more convenience. Parking: each owner has a spot for 6 months, on rotation. Since other owners have other parking, 504 #1 reimburses the other owners when it's their turn. Currently $362.50 per 6 months. Other parking options include a Village-permitted lot adjacent to the building, subject to availability, ample street parking, nearby private parking, and other permit opportunities. The location is hard to beat-directly across from Columbus Park and within easy walking distance of the Oak Park Arts District, shopping, restaurants, and public transportation. Commuters will appreciate convenient access to the CTA Blue and Green Lines and the Eisenhower Expressway (I-290). Downtown Chicago's Loop and Michigan Avenue are less than 8 miles away. A distinctive home with vintage charm, modern amenities, and an exceptional location-this one is a must-see!

504 S Austin Boulevard Unit #1, Oak Park
151 N Kenilworth Avenue Unit #4G, Oak Park
$295,000
2 Beds ⋅ 2 Baths ⋅ 12771952 MLS ⋅ NEW Status
***Seller is offering up to a $10,000 closing cost credit to help with closing costs, interest rate buy down, dishwasher/washer/dryer installation, or just to leave a little extra cushion for decorating***Stunning, move-in-ready 2BR/2BA condo in the heart of Downtown Oak Park! Completely remodeled in 2026 with new flooring, fresh paint, new fixtures, new doors, new tile, all-new appliances, a new electrical panel brought to current code, and three new GE window A/C units. Bright, welcoming and truly ready for its next owner. Enjoy covered parking space #32, private storage locker #38, building laundry, two elevators, and accessible entrances with ramps. Monthly HOA includes heat, gas, water, garbage and lawn care. The building is well cared for and features landscaped grounds, a circular drive, security cameras and convenient garage access. All of this in an incredibly walkable location near restaurants, coffee shops, local businesses, the theater, parks and everything Downtown Oak Park has to offer. Some photos may be virtually staged.

151 N Kenilworth Avenue Unit #4G, Oak Park
403 S Harvey Avenue Unit #2B, Oak Park
$185,000
1 Beds ⋅ 1 Baths ⋅ 12769043 MLS ⋅ ACTIVE Status ⋅ Terra Cotta Court BLDG.
Welcome home to this bright vintage condo in Oak Park's Ridgeland Historic District! the original hardwood floors were freshly refinished and glow throughout. The kitchen features granite countertops, maple cabinets and soon to be delivered new stainless appliances. The large formal dining room is ready for dinner parties and holiday gatherings. In-unit laundry adds everyday convenience. The location makes life easy: walk to both the Blue Line and Green Line L trains, enjoy nearby restaurants, shopping, and schools, and hop on I-290 in minutes. Vintage charm and modern convenience in one great spot, so schedule your showing today!

403 S Harvey Avenue Unit #2B, Oak Park
821 N Harlem Avenue, Oak Park
$420,000
2 Beds ⋅ 3 Baths ⋅ 12764277 MLS ⋅ ACTIVE Status
Location and convenience meet in this meticulously maintained, three-level townhome bordering the Frank Lloyd Wright Historic District. Positioned just steps from vibrant downtown Oak Park, this turnkey residence offers over 1,900 square feet of pristine living space. The thoughtful floor plan features two spacious bedrooms, each complete with a generous walk-in closet, and convenient access to the third level laundry room. The primary suite serves as a true retreat, boasting its own private balcony and an ensuite bathroom equipped with a soaking tub, walk-in shower, and dual-sink vanity. On the main floor, a sun-drenched living area centers around a cozy fireplace with a seamless flow ideal for entertaining. The bright, functional kitchen features a charming breakfast nook alongside access to a second outdoor balcony. A ground-level den offers versatile extra space-perfect for a home office, gym, or media room. Complete with the rare village luxury of an attached two-car garage, this home combines effortless living with an unbeatable location. Located in a highly walkable neighborhood with easy access to local shopping, dining, and transit. Zoned for highly sought-after Holmes Elementary, Brooks Middle, and OPRF High School. A rare opportunity to own a flawless, move-in-ready home in one of Chicagoland's most historic and vibrant communities. Property is in great condition but is being sold AS-IS

821 N Harlem Avenue, Oak Park
420 S Home Avenue Unit #109N, Oak Park
$189,000
1 Beds ⋅ 1 Baths ⋅ 12768293 MLS ⋅ ACTIVE Status
Welcome home to this beautifully remodeled 1-bedroom, 1-bath condo in the heart of Oak Park! Located on the first floor of a well-maintained, professionally managed building, this move-in-ready home offers a bright, inviting interior with western exposure and a private balcony-the perfect spot for morning coffee or relaxing at the end of the day. One of the biggest advantages of this first-floor location is that **only first-floor units in the building are permitted to have pets and hard-surface flooring**, making this condo an especially desirable find. Inside, you'll enjoy scratch-resistant luxury vinyl flooring throughout and an updated kitchen featuring custom quartz countertops designed to resist scratches and stains, stainless steel appliances, and a dishwasher. Convenient on-site laundry is located just outside the unit. Storage unit 109 is on the same floor. Parking is space #10. And the location is hard to beat! Just minutes from vibrant Downtown Oak Park, you'll have easy access to an incredible variety of restaurants, coffee shops, shopping, parks, entertainment, and public transportation. Beautifully updated, pet-friendly, move-in ready, and ideally located-this is Oak Park living with some perks you simply won't find in every unit in the building. Schedule your showing today!

420 S Home Avenue Unit #109N, Oak Park
420 S Kenilworth Avenue Unit #18, Oak Park
$199,900
2 Beds ⋅ 1 Baths ⋅ 12766009 MLS ⋅ PRICE CHANGE Status
LOCATION, LOCATION, LOCATION. & MOTIVATED SELLER. Looking for a quick sale... Great 2 BR/1BA Condo, freshly painted and new carpeting throughout. Perfect for 1st time home buyers, or ambitions INVESTER. Located in the Heart of Oak Park near I-290 Expressway with great schools, shopping, restaurants, public transportation via Metra, ALL walking distances away. Coin operated laundry on site, an assigned parking. Great time to buy, as winter is coming soon and the HOA includes heating and snow removal in monthly assessment. This could also be a great pickup for an investor...

420 S Kenilworth Avenue Unit #18, Oak Park
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