Recently Sold Homes in Winston Woods, IL

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SOLD OCT 1, 2025

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
Step into this beautifully unique split-level home that combines rustic charm with modern comfort. Featuring a warm and inviting log cabin-inspired decor throughout, this 4-bedroom, 2.1-bath home offers an open-concept main level that's perfect for entertaining. The spacious kitchen and living areas flow seamlessly together with exposed wood accents, natural textures, and cozy finishes. Retreat to your own private indoor hot tub for year-round relaxation. The home also includes a sub-basement offering additional storage or potential living space. A truly special home that blends character, comfort, and functionality!

$360,000 Last sold price

4 beds2.5 baths1,915 sq ft

616 N Pinecrest Rd, Bolingbrook, IL 60440

SOLD NOV 25, 2025

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
Welcome home! This beautifully updated 4-bedroom, 2.1-bath home in the Winston Woods subdivision was fully remodeled in 2020 and offers over 2,400 square feet of comfortable living space with a smart, functional layout. The main level features a modern kitchen with granite countertops and stainless steel appliances, a bright living and dining area, a cozy family room with a brick fireplace, a powder room, and a sunroom. Upstairs, you'll find four bedrooms and two updated full bathrooms. The primary suite includes a private bathroom and a walk-in closet. The finished basement includes a spacious rec room, perfect for entertaining or extra living space. Attached 2-car garage with newer overhe

$439,000 Last sold price

4 beds2.5 baths2,470 sq ft

427 Charlestown Dr, Bolingbrook, IL 60440

SOLD OCT 10, 2025

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
Don't miss the opportunity to see this beautiful 3 bedroom and 2 bath charming move-in-ready home. Large open concept offers dinning and living room with a view to the family room. The three bedrooms on first level are on one side of the house for more privacy. The main bedroom has its own full bathroom for convenience. Full Basement partially finished with a lot of potential. 4th bedroom in the basement with the possibility of a 5th bedroom there. Hardwood floors throughout the house installed in 2006. Windows and doors replaced in 2020. Roof is about 10 years old. Driveway 7 years old. Hot water tank was installed in 2018. Sump pump 2019. Huge back yard with a deck for your cookouts. Enjo

$390,000 Last sold price

4 beds2 baths1,587 sq ft

722 N Pinecrest Rd, Bolingbrook, IL 60440

SOLD OCT 17, 2025

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
Welcome to your dream home! This stunning 5-bedroom, 3-bath raised ranch has been impeccably remodeled with modern elegance and comfort in mind. Step onto the charming covered front porch and into a welcoming foyer that sets the tone for the rest of this gorgeous home. The luxurious hardwood staircase leads you into bright, open living spaces filled with natural light. The beautiful features stainless steel appliances, a specious kitchen island perfect for both everyday meals and entertaining guests. All bathrooms are beautifully updated. 5th bedroom could be your office (additionally installed can lights). Modern light fixtures interior and exterior of the house. Brand new roof, windows, g

$485,000 Last sold price

5 beds3 baths2,650 sq ft

3 Charlestown Ct, Bolingbrook, IL 60440

SOLD SEP 22, 2025

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
Step inside this beautifully remodeled 4-bedroom, 2-bathroom raised ranch in the desirable Bolingbrook area. Offering the perfect blend of modern updates and comfortable living, this home is ready for you to move right in and enjoy. The spacious layout provides ample room, with four generously sized bedrooms and two RECENTLY 2025 renovated bathrooms. Imagine weekend barbecues in the big yard, offering endless possibilities for outdoor fun and relaxation. You'll also appreciate the convenience of a 2-car garage, providing secure parking and extra storage. Step out onto the deck, an ideal spot for enjoying your morning coffee or unwinding after a long day. Roof is 15 years old, windows were

$380,000 Last sold price

4 beds2 baths1,950 sq ft

9 Shilling Ct, Bolingbrook, IL 60440

Property at 725 N Pinecrest Rd, Bolingbrook, IL 60440, 4 beds, 3 baths

$400,000 Last sold price

4 beds3 baths2,050 sq ft

725 N Pinecrest Rd, Bolingbrook, IL 60440

Property at 226 Hampshire Ln, Bolingbrook, IL 60440, 3 beds, 2 baths

$355,000 Last sold price

3 beds2 baths1,800 sq ft

226 Hampshire Ln, Bolingbrook, IL 60440

Property at 411 Liberty Dr, Bolingbrook, IL 60440, 4 beds, 2.5 baths

$351,000 Last sold price

4 beds2.5 baths1,915 sq ft

411 Liberty Dr, Bolingbrook, IL 60440

Property at 5 Derbyshire Ct, Bolingbrook, IL 60440, 5 beds, 3 baths

$475,000 Last sold price

5 beds3 baths2,650 sq ft

5 Derbyshire Ct, Bolingbrook, IL 60440

Property at 229 Charlestown Dr, Bolingbrook, IL 60440, 4 beds, 2 baths

$362,000 Last sold price

4 beds2 baths1,950 sq ft

229 Charlestown Dr, Bolingbrook, IL 60440

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SOLD NOV 7, 2025

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
Almost 2 Acres with an outstanding Pond View. This unique Farmhouse, built in 1890, features a Great room addition added 37 years ago. The charming covered Porch at the front entrance offers an amazing view of the pond. The Vaulted Great room includes two Skylights, a Brick fireplace with a wood mantel and remote electric for modern convenience, track lighting, and patio doors leading to a huge Deck and Koi Pond. The Open country kitchen provides ample storage, a breakfast bar, and eat-in table space, along with a Formal Dining room featuring hardwood floors. The spacious living room includes a brick wood-burning fireplace with a mahogany mantel, which has not been used by the current owner

$670,000 Last sold price

3 beds2 baths2,602 sq ft

8521 State Route 53, Naperville, IL 60565

SOLD NOV 12, 2025

$443,000 Last sold price

5 beds2.5 baths2,104 sq ft

800 N Ashbury Ave, Bolingbrook, IL 60440

SOLD OCT 24, 2025

$274,900 Last sold price

3 beds2.5 baths1,460 sq ft

514 Jill Ln, Bolingbrook, IL 60440

SOLD BY REDFIN SEP 11, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
Welcome home to this FULLY REHABBED(2013) gem featuring an attractive open floor plan with beautiful hardwood floors throughout the main level. The kitchen offers stainless steel appliances, granite countertops, and ample cabinet and counter space. The bright and inviting living and dining areas are filled with natural light. Three spacious bedrooms and a full bathroom with shower complete the main level. The lower level offers a large versatile space, perfect for a rec room, home office, or potential fourth bedroom, along with another full bathroom and a spacious laundry area. Step outside to your fully fenced backyard oasis with a generous deck-ideal for entertaining or relaxing while enj

$365,000 Last sold price

3 beds2 baths1,726 sq ft

357 Sword Way, Bolingbrook, IL 60440

SOLD NOV 7, 2025

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
Welcome to this Beautiful VINTAGE AND CONTEMPORARY STYLE TOWNHOUSE located in the Clusters of Bolingbrook. This beautiful newly renovated home features a NEW modern stylish Kitchen with an off-White Cabinetry and Quartz kitchen Tops. This homes features 3 Bedrooms, with a walk in closet in the primary room, 1.5 luxurious baths and additional loft space for entertainment or office space. A combine spacious Living and Dining room with CATHEDRAL ceilings . A FAMILY ROOM to enjoy your holidays and family time. Hardwood floors throughout the first floor, New Carpet in the second floor. Other HIGHLIGHTS of the property include, New fixtures, NEW roof, and much more. WELCOME TO YOUR NEW HOME!

$310,000 Last sold price

3 beds1.5 baths1,971 sq ft

460 Michelangelo Dr, Bolingbrook, IL 60440

BOUGHT WITH REDFIN SEP 22, 2025

ABOUT THIS HOME
Recently Sold Home in Winston Woods, IL:
This well-appointed 3 bed/2.1 bath home with an attached 3-car garage offers 2,897 sq ft of thoughtfully-designed living space on a 10,249 sq ft lot. The home's southern exposure and skylights provide the primary living areas with abundant natural light throughout the day. The residence boasts numerous upgrades, including a high-end kitchen equipped with Amish cabinetry, granite flooring, professional-grade appliances, an oversized central island with a prep sink, and a separate wet bar, ideal for culinary enthusiasts and entertaining. Bring the party outdoors to the back patio, which includes water and gas hookups for an outdoor kitchen, as well as a covered entertainment space. Despite it

$530,000 Last sold price

3 beds2.5 baths2,897 sq ft

674 Goldenrod Dr, Bolingbrook, IL 60440

Redfin Corporation

Property at 857 Bonnie Brae Ln, Bolingbrook, IL 60440, 4 beds, 2.5 baths

$427,500 Last sold price

4 beds2.5 baths3,533 sq ft

857 Bonnie Brae Ln, Bolingbrook, IL 60440

Property at 209 Monroe Rd, Bolingbrook, IL 60440, 3 beds, 2.5 baths

$261,000 Last sold price

3 beds2.5 baths1,320 sq ft

209 Monroe Rd, Bolingbrook, IL 60440

Property at 742 Feather Sound Dr, Bolingbrook, IL 60440, 4 beds, 2.5 baths

$540,000 Last sold price

4 beds2.5 baths2,152 sq ft

742 Feather Sound Dr, Bolingbrook, IL 60440

Property at 207 Walker Dr, Bolingbrook, IL 60440, 3 beds, 2.5 baths

$252,000 Last sold price

3 beds2.5 baths1,460 sq ft

207 Walker Dr, Bolingbrook, IL 60440

Property at 841 Bonnie Brae Ln, Bolingbrook, IL 60440, 4 beds, 2.5 baths

$443,000 Last sold price

4 beds2.5 baths2,600 sq ft

841 Bonnie Brae Ln, Bolingbrook, IL 60440

Property at 551 Goodwin Dr, Bolingbrook, IL 60440, 2 beds, 3.5 baths

$315,000 Last sold price

2 beds3.5 baths1,750 sq ft

551 Goodwin Dr, Bolingbrook, IL 60440

Property at 725 N Ashbury Ave, Bolingbrook, IL 60440, 4 beds, 2.5 baths

$425,000 Last sold price

4 beds2.5 baths2,104 sq ft

725 N Ashbury Ave, Bolingbrook, IL 60440

Redfin Corporation

Property at 213 Pamela Dr, Bolingbrook, IL 60440, 3 beds, 2.5 baths

$301,000 Last sold price

3 beds2.5 baths1,990 sq ft

213 Pamela Dr, Bolingbrook, IL 60440

Property at 561 Goodwin Dr, Bolingbrook, IL 60440, 3 beds, 2.5 baths

$337,500 Last sold price

3 beds2.5 baths1,890 sq ft

561 Goodwin Dr, Bolingbrook, IL 60440

Property at 494 Ridge Ln, Bolingbrook, IL 60440, 2 beds, 2 baths

$397,900 Last sold price

2 beds2 baths1,468 sq ft

494 Ridge Ln, Bolingbrook, IL 60440

$550,000

4 beds2.5 baths2,306 sq ft

851 Bluestem Dr, Bolingbrook, IL 60440

$330,000

4 beds2 baths2,964 sq ft

324 Falcon Ridge Way, Bolingbrook, IL 60440

Property at 829 Bonnie Brae Ln, Bolingbrook, IL 60440

$72,000 Last sold price

— beds— baths— sq ft

829 Bonnie Brae Ln, Bolingbrook, IL 60440

Property at 355 Falcon Ridge Way, Bolingbrook, IL 60440

$325,000 Last sold price

— beds— baths— sq ft

355 Falcon Ridge Way, Bolingbrook, IL 60440

Based on information submitted to the MLS GRID as of Thu Nov 27 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. 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.

Recently Sold Homes in Winston Woods

There are currently 10 recently sold homes for sale in Winston Woods at a median listing price of $388K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winston Woods stay on the market for 43 days and receive 4 offers. Popular neighborhoods include Farmingdale Village, Indian Oaks, University Heights, Old Bolingbrook, and Woodbridge Estates. This map is refreshed with the newest listings in Winston Woods every 15 minutes.

In the past month, 4 homes have been sold in Winston Woods. Find your dream home in Winston Woods using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winston Woods are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winston Woods. If you're looking to sell your home in the Winston Woods area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winston Woods with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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