Browse All Oak Park IL Between $400K - $500K Properties for Sale

Elevate your business presence at 412 Madison Street, a versatile two-story office space that perfectly balances professional focus with collaborative energy. This thoughtfully designed property is engineered for productivity, offering four private offices for deep work and an expansive conference and flex area perfect for brainstorming sessions and client presentations. Plug and Play efficiency: Stay connected with a building already wired for high-speed Ethernet across all workspaces, ensuring your team is ready to hit the ground running. Smart Infrastructure: Enjoy peace of mind with commercial-grade electrical and plumbing systems, updated to modern standards. Professional Amenities: A dedicated kitchenette supports your daily operations, while the lower level provides essential, convenient storage, along with on-site parking. The "Work-Life" Perk: Step outside to your own private garden area-a hidden gem that serves as a serene backdrop for informal meetings or a restorative midday break. A Location That Connects: Situated in the vibrant Oak Park business community, 412 Madison Street puts you at the nexus of convenience and culture. You are minutes away from world-class dining, boutique shopping, and the historic charm of a village known for its architectural significance. Commuting is effortless, whether your team or clients are coming from the Chicago Loop or the suburbs. The property is ideally positioned with easy access to major transportation hubs, including the CTA Green and Blue Lines and the Metra Union Pacific West Line, making this one of the most accessible and connected business addresses in the area.

412 Madison Street, Oak Park

$499,000

4 Beds ⋅ 2 Baths ⋅ 12703932 MLS ⋅ CONTINGENT Status

** Multiple offers received. Highest and best due 5pm Sunday 7/19** Character, creativity, and a location you'll love. This charming 4-bedroom, 2-bath home is nestled on a picturesque block in Oak Park's sought-after Arts District, where historic charm and artistic spirit come together. Inside, you'll find rich hardwood floors, original built-ins, abundant natural light, and inviting spaces full of personality. The vaulted kitchen, complete with skylights, creates a bright and inspiring gathering space, while the flexible floor plan offers room to work, relax, and entertain. A welcoming enclosed front porch extends your living space and provides the perfect spot to enjoy your morning coffee or unwind at the end of the day. Outside, the thoughtfully landscaped, low-maintenance yard offers beauty without the upkeep, creating a peaceful retreat that's easy to enjoy. Full of warmth, character, and timeless appeal, this is a home that embraces its unique style while offering comfortable everyday living-all in one of Oak Park's most vibrant neighborhoods. Updates: Tear off Roof and gutter guards ~2021, HWH 2021, Refrigerator 2024, Back deck 2024, Garage 2012

824 S Taylor Avenue, Oak Park

$499,000

3 Beds ⋅ 2 Baths ⋅ 12704638 MLS ⋅ CONTINGENT Status

735 Gunderson Avenue, Oak Park

$480,000

3 Beds ⋅ 2 Baths ⋅ 12694752 MLS ⋅ CONTINGENT Status

If you're a fan of vintage details, you'll love this classic Oak Park three bedroom, two bathroom bungalow where charm and character meet modern convenience. Situated on a tree-lined cul-de-sac, this home offers beautiful hardwood floors, a spacious eat-in kitchen with a pantry for extra storage, a separate dining room for more formal occasions, a large rec room in the basement that's perfect for additional living space, hobbies, movie nights, or entertaining, a two-car garage with a parking pad, and proximity to shopping, entertainment, and the Blue line. Relax on the front porch in the spring and summer, and imagine the possibilities of the family room for year-round use. It could be a playroom, a home office, a guest space, or just about anything you like. The seller also has taken on the expense of waterproofing the basement so you don't have to, as well as adding a tankless water heater so you'll never run out of hot water. Please ask your agent to show you the list of improvements. If you've been wanting to buy in Oak Park at an exceptional price, now is your chance, but don't wait! This home has all the best Oak Park has to offer.

1180 Gunderson Avenue, Oak Park

$419,000

3 Beds ⋅ 2 Baths ⋅ 12704288 MLS ⋅ CONTINGENT Status

Enchanting historic brick cottage draped in lush ivy, blending vintage charm with modern updates in one of Oak Park's most desirable neighborhoods. This freshly updated 3-bedroom home is straight out of a storybook, step inside to soaring 10-foot ceilings, gleaming hardwood floors, and sun-filled living spaces accented by beautiful original woodwork. The heart of the home is the newly redesigned kitchen featuring custom cabinetry, stylish finishes, new black stainless steel appliances, and a huge walk-in pantry (formerly a bedroom) that's perfect for storage, a home office, craft room, or the organized chef who's secret ingredient is love aka lime zest. Retreat upstairs to your spacious primary suite with its newly added private full bath, a rare luxury in a home of this era. The newly finished walkout basement provides incredible flexibility ready to become your recreation room, guest suite, or TikTok studio for your workout videos. Outside, your own private backyard oasis awaits. Relax on the newly refurbished deck overlooking lush gardens, entertain friends on the patio, or simply enjoy a quiet evening surrounded by mature landscaping. An oversized two-car garage and additional storage complete the package. Located in the award-winning Oak Park school districts, convenient access to CTA Blue Line, Metra, I-290, parks, restaurants, shopping, non-stop dog walking traffic and everything that makes Oak Park one of Chicagoland's most sought-after communities. See this one before it vanishes like the storybook dream it is...

1137 S East Avenue, Oak Park

$449,000

2 Beds ⋅ 2 Baths ⋅ 12702024 MLS ⋅ PRICE CHANGE Status

Beautiful 2 bed, 2 full bath condo in the heart of Oak Park. This unique round-design unit features an open-concept living, dining, and kitchen layout with abundant natural light from expansive windows throughout. Well-maintained oak hardwood floors, spacious kitchen with large island, granites countertops, breakfast bar, stainless steel appliances, and private balcony. The primary suite offers a walk-in closet and en-suite bath with double vanity, separate shower, and soaking tub. In-unit laundry, central HVAC, extra storage, and 1 indoor parking space included. Walk to the CTA Green Line Ridgeland Station, Metra Oak Park Station, Easy access to I-290 and Downtown Chicago. Lots restaurants, shops, Oak Park Farmers' Market, Jewel-Osco, Whole Foods, and Pete's Fresh Market near by.

106 S Ridgeland Avenue Unit #304, Oak Park

$425,000

6 Beds ⋅ 3 Baths ⋅ 12701096 MLS ⋅ RE-ACTIVATED Status

1428 N Austin Boulevard, Oak Park

$455,000

3 Beds ⋅ 1 Baths ⋅ 12697325 MLS ⋅ CONTINGENT Status

This beautifully updated ranch may be the most eye-catching home on the block! Nestled in the desirable Arts District neighborhood, this charming 3-bedroom, 1-bath home seamlessly blends classic character with stylish modern updates. From the moment you arrive, you'll appreciate the home's inviting curb appeal and thoughtfully designed interior. The spacious living room features a skylight, partial vaulted ceiling, cozy fireplace, and a charming reading nook that creates a warm and welcoming atmosphere. Engineered wood flooring flows throughout the main level. The open-concept kitchen, showcases modern custom cabinetry, quartz countertops, designer tile backsplash, breakfast bar seating, cooktop with stainless steel range hood, and stainless steel appliances. A separate dining area provides the perfect space for everyday meals and entertaining. The primary bedroom offers a striking accent wall, custom lighting, and a generously sized closet. Two additional bedrooms provide spacious and versatile accommodations, each featuring abundant natural light and large closets, making them ideal for family members, guests, a home office, or creative workspace. The beautifully appointed full bath features dual vanities, tiled flooring, mirrored medicine cabinet, a walk-in shower with handheld fixture, and upscale finishes throughout. A convenient mudroom is located just off the rear entrance. The full, partially finished basement adds valuable living and storage space with epoxy flooring, custom storage cabinetry, laundry area, and exposed trusses that create a unique loft-inspired feel. Imagine the possibilities! Step outside to enjoy the private fenced yard, ideal for relaxing, entertaining, or outdoor gatherings. Additional highlights include a newer garage built in 2005, replacement windows throughout and updated 200-amp electrical service. Move-in ready and loaded with character, style, and functionality-this is a home you won't want to miss!

1116 S Harvey Avenue, Oak Park

$500,000

4 Beds ⋅ 2 Baths ⋅ 12680617 MLS ⋅ PENDING Status

Presenting an extraordinary opportunity in the heart of Oak Park.A stately oversized 4 BR/2BA brick bungalow that has been lovingly cared for by the same family for over 75 years. This remarkable home is a testament to timeless craftsmanship and the enduring pride of ownership that only multi-generational care can provide. From the moment you arrive, the substantial brick facade commands attention, offering a sense of permanence and quality that defines this architectural gem. Inside, a treasure trove of original details awaits, each element thoughtfully preserved through decades of devoted stewardship. The home's original stained glass windows cast warm, jewel-toned light and serve as both windows and works of art. The floors are nothing short of spectacular. Featuring intricate inlaid patterns and rich, warm tones, the hardwood flooring flows throughout the main living areas, adding elegance and character that cannot be replicated in modern construction. Exquisite crown moulding adorns the principal rooms, reflecting the attention to detail and superior craftsmanship of the era. Perhaps the most compelling feature of this home is its history. Having remained in the same family for over 75 years, this property has been the backdrop for countless memories, celebrations, and daily moments of joy. This is more than a house-it is a piece of Oak Park's residential heritage, offered for the first time in generations. An exceptional opportunity for discerning buyers who appreciate vintage craftsmanship, architectural integrity, and the immeasurable value of a home with a soul.

801 Gunderson Avenue, Oak Park

$430,000

3 Beds ⋅ 2 Baths ⋅ 12665251 MLS ⋅ CONTINGENT Status

No HOA fees, ever. Experience true fee-simple ownership in this fully renovated 3-bedroom, 1.5-bath brick townhouse that lives like a single-family home. Located in the prestigious Frank Lloyd Wright District and the sought-after Holmes Elementary school district, this home is close to the Green Line, Metra, Trader Joe's, Broken Tart, and the best of Lake Street's dining. The main level has been transformed into a seamless open-concept space, anchored by a kitchen island, high cabinetry, and new engineered-hardwood flooring. New appliances and backsplash finish the kitchen. Beyond the aesthetic upgrades, the home features essential, high-value infrastructure: new copper plumbing, a modern electrical panel, and newer mechanicals-giving you total peace of mind. Upstairs, the full bath has been completely reimagined with a new walk-in shower, double-sink vanity, and ceramic floor. Three large bedrooms with refinished hardwood floors fill out the upper level, where new light fixtures, new doors, and new molding carry the renovation into every corner. A partially finished basement provides flexible space for a family room, dedicated laundry, and ample storage. Finished with a new front picket fence and detached garage, this turnkey home is ready for you to move in and enjoy. Don't miss your chance to own a low-maintenance, high-style home in the heart of Oak Park.

1120 Superior Street, Oak Park

$425,000

3 Beds ⋅ 4 Baths ⋅ 12675801 MLS ⋅ CONTINGENT Status

Check out this amazing newer-construction townhome right in the heart of beautiful downtown Oak Park. The place feels fresh and clean, with big bright rooms that really make it shine. As you walk in, the main level greets you, leading into a formal living area that features a stately gas fireplace and gorgeous oak floors. The kitchen is a dream, boasting stainless appliances and tons of counter space for all your cooking adventures. You can host your celebrations in the dining area, which opens up to a back patio that's perfect for grilling. On the second level, you'll find a grand primary suite with a full bath and an entire wall of closets! Plus, there's a laundry area, a main full bath, and a spacious second bedroom. Then, head to the top level where you'll discover a versatile space that can be a third bedroom, office, or family room. It also has another full bath and a brand new private sun-deck for those sunny days. This home comes with a deeded one-car parking space, a storage room, and so much more. It's meticulously maintained and beautifully appointed-this luxurious townhome could be just what you're looking for!

609 South Boulevard Unit #E, Oak Park

$479,900

3 Beds ⋅ 3 Baths ⋅ 12681425 MLS ⋅ CONTINGENT Status

There is so much to love about this spacious 3-bedroom, 2.5-bath Oak Park home. Lovingly maintained by the same owners since 1976, this home is located on one of the village's charming brick streets and offers a wonderful blend of vintage character, generous indoor and outdoor living space. Inside, you'll find beautiful hardwood floors, original moldings, and a wood-burning fireplace that anchors the living room. A sunny first-floor family room provides additional living space and overlooks the backyard, making it the perfect spot to relax or gather with family and friends. The second floor features a comfortable primary suite with a private full bath and ample closet space, along with two additional generously sized bedrooms. The unfinished basement offers excellent potential for future expansion and is ready to be transformed into additional living, recreation, or work-from-home space. Outside, there is a newer tear-off roof (2023), a-tiered deck, and a deep backyard filled with established perennials and highlighted by a beautiful Russian olive tree. A rare three-car garage and side drive provide abundant parking and storage. Conveniently located with quick access to the train and all the shopping, dining, parks, and amenities that make Oak Park such a desirable community, this home is an outstanding opportunity. If you're looking for a roomy three-bedroom home on a large lot with character and potential, this is it!

614 N Humphrey Avenue, Oak Park

$439,000

2 Beds ⋅ 2 Baths ⋅ 12672209 MLS ⋅ ACTIVE Status

Exceptional location in Downtown Oak Park! This luxury building is nestled in the midst of all downtown Oak Park has to offer: outstanding restaurants, shops and the Metra Train, Green Line El and Pace Bus System. Minutes to the Frank Lloyd Wright Home and Studio and Oak Park's Historic District of homes. Within the community are top elementary, middle and high schools as well as three universities. Two bedrooms and two baths with in unit laundry. Open floor plan, perfect for entertaining. Private balcony. Very well maintained building. One deeded garage parking spot conveniently located near the elevator. Storage locker. Elevator building. Professional property management company. Solid financial budget with healthy reserves. Highly sought after building with the FFC health club located in the building--separate membership required. Holley Court parking garage is located behind the building for guest parking. Do not miss this rare opportunity to own a unit in a premier downtown Oak Park location. An additional garage parking space may be available for sale.

1124 Lake Street Unit #503, Oak Park

$429,900

3 Beds ⋅ 3 Baths ⋅ 12671323 MLS ⋅ PRICE CHANGE Status

425 S Harvey Avenue Unit #E, Oak Park

$465,000

5 Beds ⋅ 3 Baths ⋅ 12667016 MLS ⋅ ACTIVE Status

Nestled directly across from beautiful Maple Park, this spacious 2-flat presents a rare opportunity for homeowners, investors, and value-add buyers alike. Situated on an oversized lot, this property offers generous living space, strong rental potential, and room to create additional equity through future improvements. The building features two sizable units with classic character and functional layouts. The unfinished basement provides exciting upside with the potential to duplex the first-floor unit, creating expanded living space, a larger owner's suite, or an enhanced income-producing configuration (subject to municipal approval). Enjoy scenic park views, abundant natural light, and a location that combines neighborhood charm with convenient access to schools, shopping, dining, and transportation. Whether you're looking to live in one unit while collecting rental income, renovate and increase value, or add a strong asset to your portfolio, this property offers multiple paths to success.

1032 S Maple Avenue, Oak Park

$495,000

5 Beds ⋅ 3 Baths ⋅ 12585413 MLS ⋅ PENDING Status

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 owner-occupants alike. Additional income from the 2 garage spots and tandem exterior spots. Each unit offers comfortable living spaces with natural light and timeless architectural details that reflect Oak Park's historic charm. Situated on a desirable tree-lined street, the property enjoys a prime location close to public transportation, parks, shopping, dining, and everything that makes Oak Park one of Chicagoland's most sought-after communities. With its classic structure, flexible living arrangements, and outstanding location, this legitimate three-flat presents a rare opportunity to own a piece of Oak Park while generating rental income. New windows on upper level. Newer boiler and roof was resurfaced few years ago. Full basement with storage for each unit. Rare opportunity! As-Is sale. More financials and lease detail upon request. Tenants Rights. Allow 72 hours for showing requests.

511 N Taylor Avenue, Oak Park

$475,000

4 Beds ⋅ 2 Baths ⋅ 12552359 MLS ⋅ CONTINGENT Status

North Oak Park home on an extra large corner lot with lots of light inside home on a tree lined street. Hardwood floors throughout, double parlor living room, separate dining room, walk-in pantry, large primary bedroom w/walk-in closet. Central air conditioning. Twin rear deck, whole house water filtration system, new copper plumbing, newer 2 years old roof. Extra parking pad out side 2 car garage. No FHA or VA loans. Short walk to great schools, restaurants, shopping and CTA Green Line. Property is being sold in " as is " condition.

330 N Ridgeland Avenue, Oak Park

$477,304

2 Beds ⋅ 2 Baths ⋅ 12548098 MLS ⋅ ACTIVE Status

Welcome to Oak Park Commons! Become an owner in the first cohousing community in Illinois. Owners will 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/2 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 terrace. The kitchen boasts 42" cabinets, quartz countertops, island with breakfast bar, designer fixtures and lighting, and stainless steel appliances. The primary bedroom includes a walk-in closet and an en suite bathroom with custom shower, custom mirrors with designer lighting, and quartz countertops. 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 terrace 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 top 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: Listing photos are from Unit #406 which has the same layout/finishes, except for the balcony. This unit has a large terrace rather than a balcony.

839 Madison Street Unit #206, Oak Park

$453,114

2 Beds ⋅ 1 Baths ⋅ 12548452 MLS ⋅ ACTIVE Status

Welcome to Oak Park Commons! Become an owner in the first cohousing community in Illinois. Owners will 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. See Unit 406 listing to see more photos of what the unit finishes look like.

839 Madison Street Unit #503, Oak Park

$449,000

12489570 MLS ⋅ ACTIVE Status

Exceptional Mixed-Use Investment Opportunity in Prime Oak Park - 97 Harlem Ave Don't miss this rare chance to own a high-performing mixed-use property in the heart of vibrant, walkable Oak Park. Ideally located on high-traffic Harlem Avenue, this well-maintained building offers strong income potential through both commercial and residential components. The ground floor features a flexible retail space, currently operating as a nail salon, ideal for retail, office, or professional services. With excellent street frontage and signage visibility, this space ensures high exposure in a heavily trafficked area. Upstairs, the residential unit includes 2 bedrooms and 1 bathroom, thoughtfully designed for comfort and practicality. The unit benefits from strong rental demand, making it an attractive option for investors or owner-occupants seeking live/work potential. Mixed-use layout: Retail store/salon on the first floor with 2 restrooms and 2-bed, 1-bath apartment above Prime location near public transit, major highways, Aldi market, shopping, and dining. High-exposure commercial storefront with excellent visibility on Harlem Ave Private rear parking and access for convenience Consistent rental income with upside potential Possible tax advantages. Whether you're looking to expand your investment portfolio or establish a live/work setup in one of Oak Park's most desirable corridors, this property delivers location, income, and long-term value. Schedule your private tour today and secure this exceptional opportunity in Oak Park!

97 Harlem Avenue, Oak Park

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Between $400K - $500K Oak Park Real Estate

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