Oak Park, IL Homes for Sale under $500,000

Classic Oak Park charm meets everyday convenience in this beautifully maintained American 4-Square, set on a tree-lined, Cul de sac street just moments from parks, schools, and the Blue Line. Enter through the front door and feel the warmth of rich hardwood floors that flow throughout the home, drawing you into a sun-filled living room anchored by a decorative fireplace. Picture cozy evenings

Catherine Simon Vobornik Baird & Warner

Meticulously maintained and move-in ready, this charming Oak Park bungalow offers comfortable living with thoughtful updates throughout. Hardwood floors run across the first floor, including the spacious living room with a built-in bookcase and decorative fireplace. The adjoining sunroom, framed by wraparound windows, is perfect for a home office, reading nook, or play space. Just off the living

Margaret Sersen Redfin Corporation

MULTIPLE OFFERS RECEIVED... HIGHEST AND BEST ON 04/06/2026 AT 12 NOON (P.M.) ,,,, ADORABLE & AFFORDABLE... ABSOLUTELY CHARMING! OWNED BY ONLY THREE OWNERS! This beautifully maintained home offers space with thoughtful updates throughout. The first floor features a large living room with natural light, a formal dining room and kitchen with pantry for added storage and convenience. The second floor

Elissa Palermo Berkshire Hathaway HomeServices Chicago

Here is your opportunity to add some sweat equity to this spacious brick bungalow located on Le Moyne Parkway. The home needs updating and is reflected in the price. The separate foyer greets you as you enter the home and leads to a sunny living room featuring a wood-burning fireplace and a formal dining room. The large eat-in kitchen is great for entertaining. The first floor includes two

Heidi Rogers Baird & Warner

This approximately 2,400 square foot two unit features five bedrooms and two and a half bathrooms. The property is situated on an expansive yard, providing ample space for relaxation and outdoor enjoyment. From the enclosed front porch, residents can take in the scenic view of Maple Park, offering a peaceful and serene environment. The interior of the home boasts a versatile layout, allowing for

Nicholas Price Coldwell Banker Realty

Step into this AFFORDABLE American Four-Square coming to the public market for the first time in decades. 4 bedroom, 1.5 bath with a generous backyard - perfect for summer cookouts and room to garden and play. Freshly sanded/stained hardwood floors throughout, newly painted LR and DR, functional kitchen ready for your TLC or a thoughtful renovation, newer forced air furnace w/o central air, newer

David Gullo Gullo & Associates

Step into elevated living with this stunning luxury condominium in the heart of Downtown Oak Park. Perfectly positioned on a higher floor and set back from Lake Street, this beautifully designed home offers peace, privacy, and breathtaking western views overlooking the forest preserve, making every sunset something special. Conveniently located is the metra station within walking distance and

Melissa Walsh Coldwell Banker Real Estate Group

Fabulous Oak Park Townhouse in Prime Walk-to-Everything Location! Don't miss this rarely available 3-bedroom, 2.1 bath townhouse in the heart of Oak Park! Just a short walk to downtown's amazing restaurants, shops, and all the transit options-Metra, Green Line, and Blue Line-this home offers unbeatable convenience and comfort with an attached extra deep 1 car garage. Many recent updates include

Kyra Pych RE/MAX In The Village

Excellent investment opportunity in the heart of Oak Park! This classic vintage brick fully occupied legal three-flat offers a true multi-unit layout featuring one spacious three-bedroom unit and two renovated 1 bedroom(s). ALL units have their own washer & dryers a huge plus for tenants. The building showcases charming vintage character while providing strong income potential for investors or

Julie Bapst eXp Realty

Multiple Offers - Highest/Best due Sunday 04/19 at 12noon. This charming 2-bedroom home in central Oak Park offers wonderful flexibility with an additional bedroom in the finished basement, providing 3 total bedrooms and 2 full bathrooms. Located on desirable Grove Avenue, this property combines classic Oak Park appeal with practical modern updates. The main floor welcomes you with gleaming

Lisa Pasquesi @properties Christie's International Real Estate

BEAUTIFULLY UPDATED TOWNHOUSE IN THE MOST CONVENIENT LOCATION. MAIN LEVEL HAS A BRIGHT BEDROOM THAT LEADS TO A PRIVATE PATIO, FULL REDONE BATH AND AN ATTACHED GARAGE. SECOND FLOOR HAS A SUNNY LIVING ROOM WITH A FIREPLACE, HARDWOOD FLOORS AND A RECENTLY REMODELED KITCHEN AND DINING AREA. TOP FLOOR HAS TWO NICE SIZED BEDROOMS WITH NEW CARPETING, ANOTHER REDONE FULL BATH AND LAUNDRY. WALK TO

Daniel Halperin @properties Christie's International Real Estate

Dreams Do Come True If you've been longing for the white picket fence life, this thoughtfully designed multi-level condo offers it all-rich historic details, abundant character, and the perfect blend of vintage charm with modern comfort. Step inside the building's warm and inviting foyer, where the original historic banister greets you alone with fresh design updates. At the top of the stairs,

Sondra Savino Compass

Rare opportunity in the heart of Oak Park-welcome to the Mews. This newer construction 2-bedroom, 2-bath luxury condo puts you right in the middle of it all-just steps to downtown shops, restaurants, the farmers market, Metra/CTA, and everything that makes Oak Park such a great place to live. You're welcomed by a spacious entry foyer that opens into a bright, open-concept living and dining space

Zak Knebel @properties Christie's International Real Estate

Vintage architecture meets thoughtful updates in this top-floor residence in the historic E.E. Roberts building in prime Oak Park. This 3-bedroom, 2-bath condo showcases the craftsmanship Roberts is known for, with beautifully restored woodwork, period details throughout and modern amenities like assigned garage parking and central AC. A welcoming foyer opens to the spacious living room, freshly

Annie Coleman Compass

Welcome to 616 S Cuyler! An all-brick bungalow in the heart of Oak Park, full of charm, character, and personality-you'll feel it the moment you walk in. Offering 3 bedrooms and 1.5 baths, the home features hardwood floors throughout and a warm, inviting layout. The beautiful living room with an attached sunroom offers the perfect space to relax, unwind, or enjoy your morning coffee. A cozy

Melanie Croft Vylla Home

Located on the historic Austin Blvd in the historic district of Oak Park, this charming, three story all brick home offers tremendous space with a great layout and should not be overlooked! As you walk into the foyer you will appreciate the charm and character with the hardwood floors, wood trim, built in cabinets in the dining room and an overall great layout! The living room offers a fireplace

Ryan Smith RE/MAX Premier

Amazing opportunity to own a well-maintained multi-unit property on a rare double lot in one of Berwyn's most dynamic and high-traffic corridors. Perfectly positioned on Roosevelt Road, this building offers unmatched visibility and signage potential-surrounded by thriving businesses, restaurants, and retail, and just steps from public transportation. With quick access to major highways, including

Miguel Gomez Jr Smart Home Realty

Move-in ready home in an unbeatable location with soaring high ceilings, abundant natural light, and designer updates throughout. This beautifully updated 3-bedroom, 2-bath home features hardwood floors, newer windows, a modern kitchen with custom cabinetry, stone countertops, and stainless steel appliances, plus spacious living and entertaining areas that open to a large deck and landscaped

Ivan Bermudez Listing Leaders Northwest, Inc

Under Contract.

Edwin Flores Smart Home Realty

Great investment opportunity just hit the market! This solid brick 2-unit building with a finished basement offers both value and versatility. Both units feature IN-UNIT laundry, adding convenience for tenants and increasing rental appeal. The first floor unit includes 2 bedrooms and 1 bathroom. The second floor unit offers 3 bedrooms and access to a beautiful private balcony. The finished

Karen Flores Luna Realty Group

Top-floor living in a well-established River Forest elevator building - no neighbors above, abundant natural light, and nearly 1,800 square feet of thoughtfully rehabbed living space that sets a high bar for move-in ready. Completely renovated in 2024, Unit 504 was rebuilt with intention. The kitchen features flat-panel cabinetry, quartz countertops, and a custom southwest-inspired tiled

Chandra Shealey North Clybourn Group, Inc.

Fully rehabbed 2-unit property located in the heart of Austin on Chicago's far west side! This move in ready multi-unit features two updated units, offering a total of 3 bedrooms and 2 bathrooms across the property. Each unit has been thoughtfully renovated, making this an ideal opportunity for both investors and owner occupants. Whether you're looking to generate rental income or live in one

Erick Matos Realty of America, LLC

Well-maintained 2-unit building in Chicago's Austin neighborhood-perfect for investors or owner-occupants! This solid 2-flat features functional layouts in both units and has been thoughtfully updated over the years. Improvements include new windows (2021),new electrical panel, roof approximately 8 years old, newer washer & dryer and newer furnaces and water heaters in both units for added

Amanda Strickland Keller Williams Innovate

There's No Place Like Home! Set on a large double lot in one of Forest Park's most desirable locations, this charming home is ready for its new owner. Full of warmth, character, and timeless charm, this 3-bedroom, 1.1-bath home offers the perfect blend of original details and comfortable living spaces. Step inside to find beautiful hardwood floors and inviting living areas filled with natural

Anna Gillian Cramer Berkshire Hathaway HomeServices Chicago