5

Winston Woods Houses for Sale

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  • 419 Charlestown Dr, Bolingbrook, IL 60440
    419 Charlestown Dr, Bolingbrook, IL 60440
    419 Charlestown Dr, Bolingbrook, IL 60440
    /26

    $390,000

    • 4 Beds
    • 2.5 Baths
    • 2,132 Sq Ft

    419 Charlestown Dr, Bolingbrook, IL 60440

    Wonderful 2 Story 4 bedroom house in Winston Woods! Main level has hardwood flooring throughout; updated kitchen includes granite counters and appliances, formal living and dining rooms; family room with stone fireplace and sliding door to back yard. Upper level has master suite w walk-in closet & private bath; 3 additional nicely sized bedrooms & updated bathrooms. Partially finished basement

    Andrew Preze RE/MAX Professionals

    419 Charlestown Dr, Bolingbrook, IL 60440
  • 800 N Ashbury Ave Unit 8, Bolingbrook, IL 60440
    800 N Ashbury Ave Unit 8, Bolingbrook, IL 60440
    800 N Ashbury Ave Unit 8, Bolingbrook, IL 60440
    /26

    $439,900

    • 4 Beds
    • 2.5 Baths
    • 2,104 Sq Ft

    800 N Ashbury Ave Unit 8, Bolingbrook, IL 60440

    Welcome to this spacious 5 bedroom, 2.1 bath home nestled in one of Bolingbrook's most established neighborhoods, surrounded by mature trees and just minutes from the expressways. With 2104 square feet of living space, plus the basement, this home offers plenty of room to grow, including a large primary suite complete with its own cozy fireplace. The main level features a comfortable family

    Rebecca Kowalik john greene, Realtor

    800 N Ashbury Ave Unit 8, Bolingbrook, IL 60440
  • 725 N Ashbury Ave, Bolingbrook, IL 60440
    725 N Ashbury Ave, Bolingbrook, IL 60440
    725 N Ashbury Ave, Bolingbrook, IL 60440
    /28

    $437,000

    • 4 Beds
    • 2.5 Baths
    • 2,104 Sq Ft

    725 N Ashbury Ave, Bolingbrook, IL 60440

    Tucked away on a quiet street, this four-bedroom, two-and-a-half-bath home offers the perfect blend of privacy and convenience. Surrounded by mature trees and featuring a large fenced yard, this property provides a secluded, wooded feel rarely found in the Chicago suburbs. Step inside to discover a home filled with thoughtful updates: New roof (2024) for peace of mind Some new windows

    Julie Riddle @properties Christie's International Real Estate

    725 N Ashbury Ave, Bolingbrook, IL 60440
  • 3 Charlestown Ct, Bolingbrook, IL 60440
    3 Charlestown Ct, Bolingbrook, IL 60440
    3 Charlestown Ct, Bolingbrook, IL 60440
    /33

    $485,000

    • 5 Beds
    • 3 Baths
    • 2,650 Sq Ft

    3 Charlestown Ct, Bolingbrook, IL 60440

    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

    Arturas Strokovas Re/Max Millennium

    3 Charlestown Ct, Bolingbrook, IL 60440
  • 857 Bonnie Brae Ln, Bolingbrook, IL 60440
    857 Bonnie Brae Ln, Bolingbrook, IL 60440
    857 Bonnie Brae Ln, Bolingbrook, IL 60440
    /18

    $435,000

    • 4 Beds
    • 2.5 Baths
    • 3,533 Sq Ft

    857 Bonnie Brae Ln, Bolingbrook, IL 60440

    Now is the perfect time to invest in a pool home before temperatures rise. Nestled in a tranquil and private interior setting in St. Andrews Woods. Natural oak hardwood floors t/o. Open floor plan, cathedral ceilings, oversized famly room w/ fire place, adjacent to this space is a spacious four-season sunroom. Updated bathrooms with granite flooring and shower enclosures. Wide staircases and

    Halina Verzani HomeSmart Connect LLC

    857 Bonnie Brae Ln, Bolingbrook, IL 60440
Illinois Will County Bolingbrook Winston Woods

Houses for Sale in Winston Woods, Bolingbrook

Why Live in Winston Woods
Winston Woods in Bolingbrook offers a blend of suburban tranquility and urban convenience. The neighborhood is adjacent to Winston Woods Park, providing residents with ample opportunities for outdoor activities such as hiking and fishing at nearby Gateway Wetlands Park. The Promenade Bolingbrook shopping mall is a local highlight, featuring stores like Macy’s and Barnes and Noble, while grocery needs are met by Costco, Meijer, and Aldi. Dining options include Wholey Granoly for vegan meals, Taquería El Valle for Mexican cuisine, and Danny's Pizza and Burger Bar for American fare. The Bolingbrook Park District hosts free live music and entertainment every Wednesday night during the summer at the Bolingbrook Performing Art Center. The area is characterized by wide, tree-lined streets and sidewalks, with home styles ranging from traditional Ranch and Colonial Revival to bi-level homes and multi-family townhouses. Schools such as Brooks Middle and Bolingbrook High School are highly rated, contributing to the neighborhood's appeal for families. Residents benefit from a low crime risk compared to the national average. For transportation, North Bolingbrook Drive and U.S. Interstate 355 provide connectivity, with the Pace Suburban Bus and Lemont Metra station offering public transit options. Chicago Midway International Airport is 23 miles away, and healthcare services are accessible at UChicago Medicine AdventHealth Bolingbrook, just 4 miles from the neighborhood.
Learn more about living in Winston Woods

Home Trends in Winston Woods, IL

On average, homes in Winston Woods, Bolingbrook sell after 28 days on the market compared to the national average of 52 days. The median sale price for homes in Winston Woods, Bolingbrook over the last 12 months is $370,000, up 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$385,000
Average Price Per Sq Ft
$176
Number of Homes for Sale
8
Last 12 months Home Sales
57
Months of Supply
1.70
Median List Price
$389,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winston Woods, there are currently 5 houses for sale, offering a variety of options for prospective buyers. With houses ranging from $390,000 to $485,000, there's something for every budget. As of September, 2025 the median home price in Winston Woods, Bolingbrook is $389,000, while the average sale price is $372,304, providing insight into local market trends. On average, houses spend 28 days on the market before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options available to suit every lifestyle. Browse properties and houses for sale in Winston Woods, Bolingbrook and find the perfect place to call home.

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