10

Winston Woods Homes for Sale

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  • /20

    $275,000

    • 3 Beds
    • 2.5 Baths
    • 2,156 Sq Ft

    179 Roberts Rd, Bolingbrook, IL 60440

    Welcome to this beautifully maintained two-story townhome with full basement situated on a desirable Winston Village of Bolingbrook. Step into the inviting foyer that opens to updated wood laminate flooring throughout the main level. The spacious living room offers direct access to the backyard, perfect for relaxing or entertaining. Enjoy meals in the adjacent dining room featuring a large bay

    Melissa Kingsbury Redfin Corporation

    179 Roberts Rd, Bolingbrook, IL 60440
  • /32

    $409,900

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

    626 Derbyshire Ln, Bolingbrook, IL 60440

    Complete gut rehab with high quality finishes for this 2 story 4 bedrooms, 2.5 bathroom with partial finished basement on an oversized lot. New wood and carpet flooring 2025, all new paint 2025, all new windows 2025, new sliding patio door 2025, New bathrooms 2025, new landscaping 2025, new light fixtures 2025. All new interior doors 2025. Kitchen countertop 2025, kitchen backsplash 2025. Paver

    Nader Shahat Green Equities LLC

    626 Derbyshire Ln, Bolingbrook, IL 60440
  • /28

    $330,000

    • 3 Beds
    • 2.5 Baths
    • 1,990 Sq Ft

    213 Pamela Dr, Bolingbrook, IL 60440

    Step into this warm and inviting town home featuring 3 generously sized bedrooms and 2.5 bathrooms--offering plenty of space for the whole family to relax and unwind. Ideally situated directly across from Winston Woods Park, with a private deck that backs up to beautiful trees--this home offers a peaceful, scenic retreat surrounded by lush green space. Wood laminate floors cover the entire main

    Brant Sichko Baird & Warner

    213 Pamela Dr, Bolingbrook, IL 60440
  • /18

    $279,900

    • 3 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    207 Walker Dr, Bolingbrook, IL 60440

    A spacious and well-maintained home nestled in a quiet Bolingbrook neighborhood. This inviting residence offers 3 bedrooms, plus a den that has been converted into a 4th bedroom, providing flexible space for guests, an office, or a growing family. The main level features a bright and open layout with generous living and dining areas, a functional kitchen with ample cabinet space, and

    Eyaad Odeh Charles Rutenberg Realty of IL

    207 Walker Dr, Bolingbrook, IL 60440
  • /31

    $459,900

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    841 Bonnie Brae Ln, Bolingbrook, IL 60440

    Stunning Home in Highly Desirable St. Andrews Woods! Welcome to this captivating residence tucked away in the heart of St. Andrews Woods, one of Bolingbrook's most sought-after neighborhoods. Situated on nearly half an acre of lush, tree-lined property, this gem offers a rare combination of space, elegance, and natural beauty. From the moment you step inside, you'll feel the care and attention

    Deanna Mihalek Baird & Warner

    841 Bonnie Brae Ln, Bolingbrook, IL 60440
  • /42

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 2,897 Sq Ft

    674 Goldenrod Dr, Bolingbrook, IL 60440

    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,

    Michael Kozuchowski Century 21 S.G.R., Inc.

    674 Goldenrod Dr, 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
  • /56

    $499,900

    • 4 Beds
    • 3.5 Baths
    • 2,609 Sq Ft

    868 Bonnie Brae Ln, Bolingbrook, IL 60440

    Stunning 4-Bedroom Home in Desirable Saint Andrews Woods Welcome to Saint Andrews Woods! Homes in this sought-after neighborhood rarely become available, and this gorgeous 4-bedroom property is on the market for the first time. Freshly painted with new carpet and flooring, this move-in-ready home is waiting for its next owner. Step into the bright, open foyer that leads to a spacious living

    Lynda Mottola @properties Christie's International Real Estate

    868 Bonnie Brae Ln, Bolingbrook, IL 60440
  • /5

    $77,499

    • Land
    • 0.35 Acre
    • $221,426 per Acre

    829 Bonnie Brae Ln, Bolingbrook, IL 60440

    Build your dream home on this prime lot, ideally situated near Route 53 and major highways for easy access. Zoned R3, it's perfect for a single-family residence. The seller also has architectural designs available, which will be provided to the buyer at closing. Don't miss out on this fantastic opportunity!

    Janette Coss Realty of America, LLC

    829 Bonnie Brae Ln, Bolingbrook, IL 60440
  • /5

    $155,000

    • Land
    • 0.32 Acre
    • $484,375 per Acre

    792 Bonnie Brae Ct, Bolingbrook, IL 60440

    Vacant wooded lot approximately .33 of acre in prestigious St. Andrews Woods in Bolingbrook

    Jonathan Minerick Homecoin.com

    792 Bonnie Brae Ct, Bolingbrook, IL 60440

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.

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 $519,900. If you put a 20% down payment of $104,000 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,690 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $115K a year to afford the median home price in Winston Woods. 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 West 83rd, Whalon Lake, Waterfall Glen, Hawthorne Hill and South Downers Grove.
Are home prices dropping in Winston Woods?
Yes, home prices in Winston Woods are down 30% in the last 12 months.

Home Trends in Winston Woods, IL

Housing Trends

Median Sale Price
$505,000
Median Single Family Sale Price
$505,000
Median Townhouse Sale Price
$447,500
Median 2 Bedroom Sale Price
$340,000
Median 1 Bedroom Sale Price
$549,000
Average Price Per Sq Ft
$488
Number of Homes for Sale
4
Last 12 months Home Sales
59
Months of Supply
0.80
Median List Price
$519,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-17%
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