Winding Creek Estates Real Estate

Welcome to Winding Creek Estates, a hidden gem nestled in the heart of Naperville, Illinois, within the picturesque DuPage County. This charming neighborhood is renowned for its serene ambiance, making it an ideal haven for families and individuals seeking a peaceful yet vibrant community.

Winding Creek Estates boasts tree-lined streets and beautifully manicured lawns, creating an inviting atmosphere that welcomes residents home. With a mix of elegant single-family homes and contemporary designs, this neighborhood offers a variety of architectural styles to suit diverse tastes. Each home is a testament to quality craftsmanship and thoughtful design, ensuring comfort and functionality for every lifestyle.

One of the standout features of Winding Creek Estates is its proximity to top-rated schools, making it a prime location for families. Naperville School District 203 is consistently recognized for its excellence, providing children with a strong educational foundation. Additionally, the neighborhood is conveniently located near parks, recreational facilities, and scenic walking trails, encouraging an active lifestyle and fostering a sense of community.

Residents of Winding Creek Estates enjoy easy access to Naperville's vibrant downtown area, where an array of shopping, dining, and entertainment options await. From charming boutiques to gourmet restaurants, there’s something for everyone to enjoy.

Whether you’re looking to settle down in a family-friendly environment or simply seeking a tranquil retreat, Winding Creek Estates offers the perfect blend of suburban charm and urban convenience. Discover your dream home in this delightful neighborhood and experience the best that Naperville has to offer!

Newest Listings in Winding Creek Estates

$225,000

2 Beds ⋅ 2 Baths ⋅ 12709176 MLS ⋅ ACTIVE Status

Welcome to Olive Trees Condominiums in the heart of Naperville! This spacious and beautifully maintained condo offers 2 bedrooms, 1.5 bathrooms, an open-concept living area, and a private balcony perfect for relaxing or entertaining. Enjoy resort-style living in this full-amenity community, where the monthly association dues cover gas, water, heat, garbage service, snow removal, access to the swimming pool, clubhouse, tennis courts, fitness center, and party room. The only utility expense is electricity, making for truly convenient and affordable living. Inside, the owners have thoughtfully updated the home with fresh paint and newer luxury vinyl plank flooring throughout. The bright and inviting floor plan flows seamlessly into the kitchen and living spaces, creating an ideal setting for everyday living. Additional conveniences include multiple washers and dryers within the building, a dedicated storage unit located just steps from your front door, secure building access, and two included parking passes with ample guest parking available. The building is pet-friendly, and rentals are permitted. The location is second to none, within walking distance of the Riverwalk and scenic bike paths leading directly to downtown Naperville. Just minutes away are Edward Hospital, North Central College, the 5th Avenue Metra Station, major expressways, shopping, dining, and entertainment. Located within highly acclaimed School District 203, residents attend the nationally recognized Naperville Central High School. Combining exceptional schools, outstanding amenities, and an unbeatable location, this home offers the perfect blend of space, quality, value, and lifestyle. Welcome home!

264 E Bailey Road Unit #H, Naperville

$184,900

2 Beds ⋅ 2 Baths ⋅ 12712034 MLS ⋅ ACTIVE Status ⋅ Olive Trees BLDG.

Investor friendly 2-bedroom condo in the Olive Trees subdivision, located in highly acclaimed School District 203. This spacious unit offers an open floor plan with a combined living/dining area and an adjacent kitchen featuring a breakfast nook. Sliding glass doors off the living room lead to a private balcony. Both bedrooms are generously sized with excellent closet space. Key updates include a dishwasher in 2021, along with a new living room wall A/C unit in 2023. Coin operated laundry is conveniently located in the neighboring building. The unit includes two dedicated parking spaces directly in front of the building. Monthly assessments cover numerous utilities and provide access to community amenities including an outdoor pool, playground, tennis courts, and clubhouse. A solid opportunity for investors or owner occupants seeking value, convenience, and a prime Naperville/Aurora location within District 203.

224 E Bailey Road Unit #J, Naperville

$895,000

4 Beds ⋅ 4 Baths ⋅ 12704839 MLS ⋅ PRICE CHANGE Status

PRICE IMPROVEMENT! Bring your buyers today! Boasting a classic, stately Georgian architecture with an impressive full brick front and a premium paved driveway, this spectacular residence in the highly sought-after Winding Creek Subdivision has been meticulously maintained and care for. Seamlessly blending dramatic design, high-end updates, and a massive fully finished footprint, this home offers a turn-key lifestyle of pure luxury. Step through the front door into a dramatic two-story entryway that immediately sets the tone. Beautiful French doors open to reveal a formal dining room, perfect for hosting holiday feasts and intimate dinner parties. Relax in the breathtaking two-story family room, where soaring cathedral ceilings, massive windows, skylights, and a cozy fireplace create a bright, majestic space bathed in natural light. The beautiful, open kitchen is a showstopper, designed for both casual family meals and grand entertaining. The kitchen features a stunning new granite island as its centerpiece, complemented by the top-of-the-line stainless steel appliances, including a premium JennAir refrigerator and range, an oven for effortless hosting, a brand-new dishwasher. An additional dining area overlooks the beautiful yard including a paved patio that creates the perfect space for everyday meals or hosting guests. Even chores feel luxurious in the spectacular, newly renovated laundry room! Thoughtfully redesigned, it boasts high-end ceramic tile flooring, custom new cabinetry, gorgeous granite countertops, an integrated wine fridge, and a brand-new 2025 washer and dryer set. Tucked away for ultimate privacy is a dedicated first-floor office-ideal for remote professionals or a quiet study retreat. Head upstairs to find a highly desirable and incredibly flexible floor plan. The Master Suite Oasis: Your private sanctuary features a large walk-in closet and a spectacular, sun-drenched master bath. Flooded with natural light from beautiful skylights, the spa-like bath showcases a double sink vanity, a deep soaking tub perfect for unwinding, and a separate shower. Connected with a suite, a spectacular extra loft full of natural light awaits. This versatile space is perfect for a home office, a children's play area, a homework station, or a quiet reading nook. Additional bedrooms: three generously sized bedrooms with excellent closet space share a beautifully appointed full hallway bath-bringing the total to 4 second-floor bedrooms keeping the whole family close. Downstairs, discover the spacious, completely redone in 2025, finished basement. It is a beautiful, sprawling space designed for epic family gatherings, game nights, or media. It features a brand-new, modern half bath and beautiful wood vinyl flooring. Storage will never be an issue thanks to an extra-large crawl space perfect for seasonal items, holiday decor, and organization. Enjoy the peace of mind that comes with living in one of the area's most desirable neighborhoods, known for its beautiful tree-lined streets, friendly community feel, and close proximity to top-rated schools, parks, shopping, and dining. This rare combination of architectural drama and an ideal layout will not last. Schedule your private showing today!

475 Prairie Knoll Drive, Naperville

$205,000

2 Beds ⋅ 2 Baths ⋅ 12674888 MLS ⋅ ACTIVE Status ⋅ Olive Trees BLDG.

Welcome home to this beautifully appointed, turn-key garden-level condo offering the perfect blend of modern updates and cozy charm. Step inside to discover a fully renovated kitchen featuring sleek stainless steel appliances, premium granite countertops, and a timeless brick accent wall that adds rich character to the space. A stylish glass-door pantry completes the heart of this home. Quality vinyl flooring flows seamlessly throughout the rest of the layout. The two comfortable bedrooms are serviced by a fully renovated bathroom alongside a convenient, updated half-bath. Enjoy a truly carefree lifestyle with most utilities included in the monthly association. Whether you are looking for a primary residence or a low-maintenance addition to your investment portfolio, this Naperville gem is a must-see!

228 E Bailey Road Unit #A, Naperville

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