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Winston Woods Homes for Sale

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  • /33

    $507,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,193 Sq Ft

    759 Feather Sound Dr, Bolingbrook, IL 60440

    Welcome to The Woods of Feather Sound, where quality craftsmanship meets a peaceful natural setting. Offered by the original owners, this exceptional Cascade model showcases the renowned Airhart Medalist Series construction and occupies one of the neighborhood's most desirable homesites. Perfectly positioned on the quiet north end of the community, this premium lot backs to a protected nature

    Agent Photo

    Christopher Hochstedt

    Exit Real Estate Partners

    759 Feather Sound Dr, Bolingbrook, IL 60440
  • /48

    $410,000

    Pending
    • 6 Beds
    • 3 Baths
    • 2,400 Sq Ft

    7 Derbyshire Ct, Bolingbrook, IL 60440

    Welcome home to this spacious and versatile 6-bedroom residence tucked away on a quiet cul-de-sac, offering room for everyone and everything! The upper level features three generously sized bedrooms, including a spacious primary suite with a private ensuite bath, while the finished lower level adds three additional rooms that can easily serve as bedrooms, home offices, exercise rooms, playrooms,

    Agent Photo

    Chris Bishop

    eXp Realty - St. Charles

    7 Derbyshire Ct, Bolingbrook, IL 60440
  • /47

    $599,000

    Open Sun 12PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 2,675 Sq Ft

    816 Bonnie Brae Ln, Bolingbrook, IL 60440

    OFFER OFFER! LOCATION VALUE and LUXURY not found even in MILLION DOLLAR HOUSE, Fully furnished home in the prestigious St. Andrews Woods community of Bolingbrook, House with All checkmark, Surrounding Greenery giving a RESORT-STYLE living. True peace of mind-every major big-ticket upgrade. RENOVATED in 2026, this move-in-ready home features a brand-new roof (7/2026), new siding(7/2026), brand-new

    Kimberly Brown-Lewis Redfin Corporation

    816 Bonnie Brae Ln, Bolingbrook, IL 60440
  • /15

    $295,000

    $4K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    549 Norman Rd, Bolingbrook, IL 60440

    Welcome to this beautifully updated 4-bedroom, 2.5-bath townhome in the highly desirable Winston Village community! This move-in ready home offers a spacious and functional floor plan featuring a bright living room filled with natural light, a dedicated dining area, and a modern kitchen complete with white cabinetry, stone countertops, stainless steel appliances, and a pantry. A versatile

    Carson Gedaly HomeSmart Connect LLC

    549 Norman Rd, Bolingbrook, IL 60440
  • /25

    $265,000

    Open Sun 11AM - 1PM
    • 2 Beds
    • 1.5 Baths
    • 1,180 Sq Ft

    513 Dubois Cir, Bolingbrook, IL 60440

    Welcome to this well-maintained 2-bedroom, 1.5-bath townhome in the desirable Winston Village community of Bolingbrook. This inviting home features a bright and functional floor plan with spacious living and dining areas, a kitchen offering ample cabinet and counter space, and two generously sized bedrooms on the second level. The full unfinished basement provides excellent storage and endless

    Diego Marquez Realty of America

    513 Dubois Cir, Bolingbrook, IL 60440
  • /19

    $369,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,587 Sq Ft

    706 N Pinecrest Rd, Bolingbrook, IL 60440

    Welcome home to this highly desirable ranch-style residence in a prime Bolingbrook location! Conveniently situated near shopping, dining, entertainment, and everyday amenities, this well-maintained home offers the ease of single-level living combined with thoughtful updates and exceptional outdoor privacy. Featuring 3 bedrooms and 2 full bathrooms, this home boasts an inviting open-concept layout

    Bob Jaeger eXp Realty

    706 N Pinecrest Rd, Bolingbrook, IL 60440
  • /31

    $580,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,047 Sq Ft

    Unlisted Address

    Rarely available, spacious, custom home with a wide-open layout in the desirable Woods of Feather Sound subdivision. Situated on a beautiful, wooded lot, the backyard is fully fence. Across the street is the paved path into the 42 acre Gateway Wetlands park. Enjoy picturesque views and the ultimate natural escape right outside your front door! Main level features: two-story entry; Newly remodeled

    Matt Satre ERA Naper Realty, Inc.

    Unlisted Address
  • /43

    $399,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,950 Sq Ft

    4 Devon Ct, Bolingbrook, IL 60440

    Welcome to this stunning, completely updated three-bedroom, two-bath raised ranch, perfectly situated at the end of a quiet cul-de-sac, where exceptional craftsmanship, quality upgrades, and timeless style come together. Outstanding curb appeal begins with the all-new brick front facade, elegant Indiana limestone entry stair treads, beautiful 64-inch ornate glass front door, and impressive

    Kimberly Wirtz Wirtz Real Estate Group Inc.

    4 Devon Ct, Bolingbrook, IL 60440
  • /11

    $345,000

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    427 Devon Ln, Bolingbrook, IL 60440

    SHORT SALE APPROVED AT LIST PRICE! Brand new roof and siding with warranty. Incredible opportunity for investors, rehabbers, or savvy buyers looking to build instant equity. Needs only minor TLC and this property can quickly be restored to its full potential. Inside, you'll find granite countertops, stainless steel appliances, updated bathrooms, and beautiful hardwood flooring throughout the

    Nafis Noorali AAA Real Estate

    427 Devon Ln, Bolingbrook, IL 60440
  • /42

    $439,990

    Open Sun 3PM - 5PM
    • 3 Beds
    • 2.5 Baths
    • 2,578 Sq Ft

    436 Cambridge Way, Bolingbrook, IL 60440

    Welcome to your next ideal dream home! This beautifully property features 3 bedrooms, 2.5 bathrooms, plus a massive sunroom providing exceptional versatility as a potential 4th bedroom. The spacious 3-car attached garage provides ample room to comfortably house your vehicles and all your essential tools. Upon entry, you are greeted by a bright, spacious, and airy open-concept layout, leading into

    Jeffrey Sklar Beycome Brokerage Realty LLC

    436 Cambridge Way, Bolingbrook, IL 60440
  • /58

    $999,999

    Pending
    • 6 Beds
    • 4.5 Baths
    • 3,804 Sq Ft

    651 Anne Ln, Bolingbrook, IL 60440

    Your Dream Home is here. Designed by award winning architect (JB Architecture). Home features a grand open layout with high 9ft ceilings, custom venetian paint and hardwood floors throughout. Two way see-through fireplace between dining and 2 story grand family room. Step into a master kitchen and view the details. Need to work from home? don't worry... Your home office is one connection away

    Maria Orozco RE/MAX Partners

    651 Anne Ln, Bolingbrook, IL 60440
  • /31

    $290,000

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    140 Julie Rd, Bolingbrook, IL 60440

    Welcome home to 140 Julie Rd, a beautifully maintained townhome in the sought-after Winston Village subdivision. This 3-bedroom, 2.5-bath home features a finished basement, offering extra living, entertaining, and storage space, plus a kitchen with abundant cabinet storage and all appliances included. Enjoy maintenance-free living with an HOA that covers exterior upkeep (roof, siding, gutters,

    Anthony Erney RE Closing Professionals Corp

    140 Julie Rd, Bolingbrook, IL 60440
  • /18

    $203,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,188 Sq Ft

    555 Monroe Rd, Bolingbrook, IL 60440

    This spacious Winston Village home has a lot more to offer than meets the eye. The main level features a large eat in kitchen with granite counters, an island, and some stainless steel appliances, along with a separate dining room, a comfortable living room, and a convenient half bath. Upstairs, you'll find 3 generously sized bedrooms and a big full bathroom. The finished basement adds even more

    Ryan Behrens Re/Max Ultimate Professionals

    555 Monroe Rd, Bolingbrook, IL 60440
  • /17

    $284,999

    • 3 Beds
    • 2.5 Baths
    • 1,450 Sq Ft

    583 Norman Rd, Bolingbrook, IL 60440

    Beautiful Bolingbrook Townhome with Space, Style & Single-Family Living Feel! Welcome to 583 Norman Road in Bolingbrook, a spacious and beautifully updated 3-bedroom, 2.5-bath townhome offering comfort, flexibility, and modern living in a desirable location. From the moment you walk in, you will appreciate the bright open-concept living and dining area, designed for everyday comfort,

    Shirley Fields Coldwell Banker Realty

    583 Norman Rd, Bolingbrook, IL 60440
  • /26

    $300,000

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

    226 Charlestown Dr, Bolingbrook, IL 60440

    Multiple offers received. Highest and best due by 9pm Friday 7/17 Don't wait- this is your chance to own a reasonably priced home with great bones and endless potential! Offering plenty of space and a functional layout, this solid home is ready for your personal touch. Whether you're looking to make a few cosmetic updates or complete a full renovation, the possibilities are endless. The main

    Jonnie Vanderhyden Village Realty, Inc.

    226 Charlestown Dr, Bolingbrook, IL 60440
  • /28

    $429,999

    • 3 Beds
    • 2.5 Baths
    • 2,449 Sq Ft

    417 Cambridge Way, Bolingbrook, IL 60440

    Beautifully remodeled home in the highly sought-after Deerpath Woods neighborhood! This thoughtfully updated raised ranch features three spacious bedrooms and two full bathrooms on the main level, plus a fully finished lower level with a half bath, offering flexible living space perfect for a family room, home office, recreation area or potential fourth bedroom. The bright and inviting living

    Sheryl Long Village Realty, Inc.

    417 Cambridge Way, Bolingbrook, IL 60440
  • /32

    $479,900

    • 4 Beds
    • 2.5 Baths
    • 2,423 Sq Ft

    150 Winston Dr, Bolingbrook, IL 60440

    NO HOA!!!! Welcome home to a spacious and beautifully maintained 4-bedroom, 2.5-bath home offering comfort, functionality, and an unbeatable location. Step inside to find an inviting floor plan featuring soaring cathedral ceilings in the primary bedroom and en-suite bathroom, creating a bright and luxurious retreat. The oversized primary bathroom provides the perfect space to unwind after a long

    James Young Exit Strategy Realty

    150 Winston Dr, Bolingbrook, IL 60440
  • /26

    $275,000

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

    216 Douglass Way, Bolingbrook, IL 60440

    END UNIT & 2 CAR GARAGE! Welcome to your perfect retreat in Bolingbrook, Illinois! This exceptional end unit offers a luxurious living space and very functional separation. HOA includes a community pool and clubhouse for endless summer fun. Boasting two bedrooms upstairs, a den, two and a half bathrooms, a full basement with an additional bedroom, and a coveted two-car garage, this residence is

    Blake Morgan john greene, Realtor

    216 Douglass Way, Bolingbrook, IL 60440
  • /31

    $389,000

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

    5 Assembly Ct, Bolingbrook, IL 60440

    Multiple Offers Received, all offers need to be in by 12pm June 7th. Thoughtfully updated and impeccably maintained, this 4-bedroom, 2.1-bath residence is perfectly positioned on a private cul-de-sac with an oversized yard offering added space and privacy. From the moment you arrive, the extensive list of recent improvements provides confidence and convenience, including Carpeting (2026) in

    Jessica Burtch Realtopia Real Estate Inc

    5 Assembly Ct, Bolingbrook, IL 60440
  • /23

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,840 Sq Ft

    444 Cambridge Way, Bolingbrook, IL 60440

    Welcome to 444 Cambridge Way in Bolingbrook! This custom-built home offers the perfect blend of character, space, and thoughtful updates throughout. Tucked away on a quiet cul-de-sac, this beautifully maintained property offers privacy, charm, and an incredible natural setting. From the moment you arrive, you will appreciate the pride of ownership and craftsmanship that make this home truly

    Alisa Galoozis @properties Christies International Real Estate

    444 Cambridge Way, Bolingbrook, IL 60440

Winston Woods Home Prices vs. Nearby Bolingbrook, IL Neighborhoods

Winston Woods Hawthorne Hill Balstrode Park Indian Chase Meadows
Median Home Price
$360,000
$349,900
$379,950
$429,900
Median Sale Price
$360,000
-3% YoY
$350,000
-2% YoY
$370,000
+9% YoY
$422,500
+1% YoY
Median Single Family Price
$360,000
$360,000
$370,000
$422,500
Total Active Listings
11
7
2
4
Market Conditions
2 Months of Supply
Seller's Market
1 Months of Supply
Seller's Market
1 Months of Supply
Seller's Market
1 Months of Supply
Seller's Market

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 with some transit options. Winston Woods has 6 parks for recreational activities. It is somewhat dense in population with 7.0 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% of residents renting and 88% 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 $360,000. If you put a 20% down payment of $72,000 and had a 30-year fixed mortgage with an interest rate of 6.55%, your estimated principal and interest payment would be $1,830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $78K 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, 60565, 60517, 60561 and 60516.
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, Whalon Lake, South Woodridge and Hawthorne Hill.
Are home prices dropping in Winston Woods?
Yes, home prices in Winston Woods are down 1% in the last 12 months.
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