Winding Creek Estates Real Estate

Welcome to Winding Creek Estates, a hidden gem nestled in the heart of Naperville, Illinois, within the scenic DuPage County. This charming neighborhood offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place to call home.

Winding Creek Estates is characterized by its picturesque tree-lined streets, beautifully landscaped yards, and a strong sense of community. As you stroll through the neighborhood, you’ll find a variety of stunning single-family homes, each with its own unique charm. Many properties boast spacious layouts, modern amenities, and inviting outdoor spaces, perfect for family gatherings or quiet evenings under the stars.

Families with children will appreciate the top-rated schools in the area, including several highly regarded public and private institutions. The neighborhood is also conveniently located near numerous parks and recreational areas, offering ample opportunities for outdoor activities such as hiking, biking, and picnicking. The nearby Winding Creek Park features playgrounds, sports fields, and serene walking trails, providing a perfect escape for residents of all ages.

Winding Creek Estates is just a short drive from downtown Naperville, where you can explore a vibrant array of dining, shopping, and entertainment options. With its lively atmosphere and rich cultural offerings, downtown Naperville is a fantastic place to spend your weekends.

In Winding Creek Estates, you’ll discover a welcoming community where neighbors become friends, and every day feels like a retreat. Experience the charm and convenience of this delightful neighborhood, and make it your next home sweet home!

Newest Listings in Winding Creek Estates

$900,000

4 Beds ⋅ 3 Baths ⋅ 12730364 MLS ⋅ ACTIVE Status

Winding Creek living at its finest begins with a tree-lined lot, spectacular sunsets, and Springbrook Prairie just steps away. From the curb, this inviting four-bedroom, three-bath home offers a bright, welcoming presence and continues to impress with fresh interiors, abundant wood flooring, and thoughtful updates throughout. Inside, the welcoming den features decorator shelving and a volume ceiling, while the spacious dining room provides an ideal setting for entertaining. The sun-filled family room overlooks the yard and prairie, creating a peaceful backdrop through oversized windows. Two skylights, a ceiling fan, display shelving, and a striking stone fireplace with gas logs add comfort and character. The white kitchen combines everyday functionality with an open, inviting feel. It includes table space, an updated breakfast bar, and a pantry closet, while the sliding glass door leads directly to the deck for effortless outdoor dining and entertaining. Nearby, the laundry room connects to the oversized two-car garage. A versatile bonus room with outside access offers convenient space for exercise equipment, cubbies, and sports gear. Upstairs, the generous primary suite captures beautiful prairie views and features a tray ceiling, double closets, and a ceiling fan with light. The newly updated primary bath elevates the suite with a volume ceiling, new soaking tub, separate shower, new flooring, and a new vanity. Three additional spacious bedrooms, each with a ceiling fan and light, provide flexibility for family, guests, or a home office. The freshly painted and recently carpeted lower level expands the living space with a private office featuring closets, a large recreation room, and an additional area for cards or play. A crawl space and separate storage room offer ample room for organization. Outside, the deck is the perfect place to gather, unwind, and take in colorful sunsets, abundant wildlife, and peaceful prairie views. Residents can enjoy Winding Creek's parks and walking paths, while downtown Naperville is less than two miles away. Nearby shopping, including Trader Joe's, adds everyday convenience to this exceptional setting. With its inviting spaces, scenic surroundings, and desirable location, this home offers a wonderful opportunity to enjoy comfort and community in Winding Creek.

516 Prairie Knoll Drive, Naperville

$825,000

4 Beds ⋅ 4 Baths ⋅ 12773128 MLS ⋅ ACTIVE Status

Welcome to Winding Creek Estates! A fantastic opportunity to get into one of Naperville's most sought-after neighborhoods! This well-maintained brick-front home offers a spacious, thoughtfully designed floor plan, abundant natural light, and a BRAND NEW finished basement (2025) that adds even more living space! The main level is designed with connection in mind. A spacious, remodeled kitchen features a large island with seating and plenty of room for casual dining. The kitchen opens directly to the impressive family room, where vaulted ceilings, skylights, expansive windows, and a floor-to-ceiling brick fireplace with gas logs create a bright and inviting gathering space. A patio door leads to the backyard's paver patio, making it easy to enjoy the outdoors. A private first-floor office, along with separate living and dining rooms, provides plenty of flexibility. The newly remodeled laundry and mudroom, conveniently located off the garage, features new cabinetry, a beverage refrigerator, and a brand-new washer and dryer (2025). Upstairs, the spacious primary suite features a walk-in closet and private bath with dual vanities, a soaking tub, and a separate shower. A unique loft area off the primary bedroom overlooks the vaulted family room and offers the perfect spot for a second home office, reading nook, or private retreat. And there's more! The newly finished basement (2025) provides an entirely additional level of living space, offering endless possibilities for recreation, entertaining, or simply spreading out. Location is everything, and Winding Creek Estates delivers! Enjoy the sense of community that makes this neighborhood so special, with neighborhood events, an optional swim and tennis club, and a fantastic central Naperville location. Walk to the elementary school and enjoy easy access to the nearby Prairie Path, offering miles of trails for walking, running, and biking. Lovingly maintained and in excellent condition, this home offers an opportunity to move right in and make cosmetic updates over time to suit your personal style. With homes throughout Winding Creek Estates commanding significantly higher prices, this is an opportunity to enjoy the neighborhood, location, and lifestyle at an attractive price point. Quick closing possible!

475 Prairie Knoll Drive, Naperville

$195,000

2 Beds ⋅ 2 Baths ⋅ 12744079 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! Seller will sponsor a quarter percent buydown.

228 E Bailey Road Unit #A, Naperville

$199,900

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

Start Your Search

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

Winding Creek Estates Real Estate

Newest Listings in Winding Creek Estates

How much is your home worth?

How much is your home worth?