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Winston Woods Homes for Sale

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    $900,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,700 Sq Ft

    168 Winston Dr, Bolingbrook, IL 60440

    Architectural Dream Home - Modern Black & White Masterpiece Stunning new construction offering 4 bedrooms, 3.5 baths, and exceptional craftsmanship, set within a charming, established Bolingbrook neighborhood with no HOA. Ideally located just one block from Winston Woods Park, featuring wooded trails and tranquil nature views, and minutes from major expressways, dining, and The Promenade outdoor

    Agent Photo

    Jertheus Butts

    Coldwell Banker Realty

    (331) 255-4971

    168 Winston Dr, Bolingbrook, IL 60440
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    $500,000

    • 3 Beds
    • 2.5 Baths
    • 2,506 Sq Ft

    519 Charlestown Dr, Bolingbrook, IL 60440

    Located in the coveted Feather Sound subdivision, this striking 3-bedroom, 2.1-bath split-level stands out with exceptional curb appeal, featuring a brick facade, arched entry, and beautiful landscaping. Step into the welcoming foyer to reveal vaulted ceilings, exposed beam detail, and parquet hardwood floors flowing seamlessly through the living and dining rooms. The elevated dining area

    Martin Dzik RE/MAX Professionals

    519 Charlestown Dr, Bolingbrook, IL 60440
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    $258,750

    • 3 Beds
    • 2.5 Baths
    • 1,915 Sq Ft

    704 N Pinecrest Rd, Bolingbrook, IL 60440

    This SPLIT LEVEL style single family home offers 3 bedrooms and 2.5 bathrooms with approximately 1915 square feet of living space on a 0.18 acre lot. There are no inspection or financing contingencies on this cash only purchase. No Buyer Premium on this property. The buyer has the right to select their own title/closing company. The buyer is responsible for all closing costs in this transaction.

    Anthony Disano Parkvue Realty Corporation

    704 N Pinecrest Rd, Bolingbrook, IL 60440
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    $310,000

    • 4 Beds
    • 2.5 Baths
    • 1,826 Sq Ft

    574 Norman Rd, Bolingbrook, IL 60440

    This spacious, end-unit townhome in the desirable Winston Village Community is ready for its new owners! Located in a quiet neighborhood with friendly neighbors. With over 2,000 sq ft of living space, this home offers 4 bedrooms, 2.5 bathrooms, plus a versatile room that's perfect for an office, den, or media room. The master bedroom has a private bath with a large walk in closet. Key features

    Sanjesh Mankani Greatways Realty Inc

    574 Norman Rd, Bolingbrook, IL 60440

Why Live in Winston Woods

Winston Woods offers a blend of suburban tranquility and urban convenience in Bolingbrook. The neighborhood is adjacent to Winston Woods Park, which provides residents with ample outdoor activities such as hiking and fishing at nearby Gateway Wetlands Park. The Promenade Bolingbrook shopping mall is a local highlight, with big-box and department stores like Macy’s and Barnes and Noble. Grocery needs are met by Costco, Meijer, and Aldi. Local restaurants include Wholey Granoly for vegan meals, Taquería El Valle for Mexican cuisine, and Danny's Pizza and Burger Bar for American fare. The Bolingbrook Performing Art Center has weekly live music and entertainment during the summer. Housing styles range from traditional ranch-style houses and Colonial Revivals to bi-level homes and multi-family townhouses. Residential streets are lined with trees and connected by sidewalks. Students may attend highly rated schools such as Brooks Middle School and Bolingbrook High School. North Bolingbrook Drive serves as a main thoroughfare, and U.S. Interstate 355 is nearby for access to nearby areas. The Pace Suburban Bus serves the area, and the Lemont Metra station has connection to Chicago. Chicago Midway International Airport is 23 miles away. Healthcare services are accessible at UChicago Medicine AdventHealth Bolingbrook, just 4 miles from the neighborhood.

Frequently Asked Questions

Is Winston Woods a good place to live?
Winston Woods is a good place to live. Winston Woods is considered somewhat walkable and bikeable. Winston Woods has 6 parks for recreational activities. It is somewhat dense in population with 6.6 people per acre and a median age of 41. The average household income is $113,465 which is above the national average. College graduates make up 34.7% of residents. A majority of residents in Winston Woods are home owners, with 12.3% of residents renting and 87.7% of residents owning their home. A local real estate agent serving Winston Woods can help you decide if this neighborhood is the right one for you. Learn more on our Winston Woods neighborhood guide.
Is Winston Woods, IL a safe neighborhood?
Winston Woods, IL is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.
How much do you need to make to afford a house in Winston Woods?
The median home price in Winston Woods is $367,500. If you put a 20% down payment of $73,500 and had a 30-year fixed mortgage with an interest rate of 5.98%, your estimated principal and interest payment would be $1,760 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $75K a year to afford the median home price in Winston Woods. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winston Woods is $113K.
What are the best public schools in Winston Woods?
The best public schools that serve Winston Woods are:
What are the best private schools in Winston Woods?
The best private schools that serve Winston Woods are:
What are the most popular zip codes in Winston Woods, Bolingbrook, IL?
The most popular zip codes in Winston Woods, Bolingbrook, IL include 60440, 60517, 60561, 60516 and 60439.
What are the most popular neighborhoods near Winston Woods, Bolingbrook, IL?
The most popular neighborhoods near Winston Woods, Bolingbrook, IL are East Bolingbrook, West 83rd, South Woodridge, Whalon Lake and Hawthorne Hill.

Home Trends in Winston Woods, IL

Housing Trends

Median Sale Price
$357,500
Median Single Family Sale Price
$361,000
Median Townhouse Sale Price
$274,900
Average Price Per Sq Ft
$187
Number of Homes for Sale
4
Last 12 months Home Sales
62
Months of Supply
0.80
Median List Price
$367,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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