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Winston Woods Homes for Sale

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  • /39

    $469,999

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,117 Sq Ft

    638 Anne Ct, Bolingbrook, IL 60440

    ***MULTIPLE OFFERS RECEIVED. HIGHEST & BEST DUE BY SUNDAY, MAY 3rd****Welcome to 638 Anne Court, a beautifully maintained 4-bedroom, 2.5-bathroom two-story tucked into a quiet cul-de-sac in one of Bolingbrook's most established neighborhoods. With a newer roof (2023) and approximately 3,117 total square feet across three thoughtfully designed levels, this home delivers the space, light, and

    Agent Photo

    Tina Hollins

    Coldwell Banker Realty

    (331) 253-4474

    638 Anne Ct, Bolingbrook, IL 60440
  • /16

    $180,000

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

    230 Douglass Way, Bolingbrook, IL 60440

    Welcome to your opportunity in the heart of Bolingbrook! This desirable end-unit townhome offers a rare combination of space, functionality, and value-perfect for buyers looking to personalize a home and build equity. Featuring 2 bedrooms, a den, 2.5 bathrooms, a full basement, and a highly sought-after 2-car garage, this residence provides a flexible layout designed for everyday living and

    Agent Photo

    Jertheus Butts

    Coldwell Banker Realty

    (331) 267-6836

    230 Douglass Way, Bolingbrook, IL 60440
  • /36

    $799,998

    New Construction $100K PRICE DROP
    • 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 approx. 3,700 sq ft in a desirable Bolingbrook neighborhood with no HOA. Located one block from Winston Woods Park with wooded trails and close to expressways, dining and The Promenade. Striking black-and-white exterior, cement driveway and attached garage with EV-ready

    Agent Photo

    Jertheus Butts

    Coldwell Banker Realty

    (331) 255-4971

    168 Winston Dr, Bolingbrook, IL 60440
  • /38

    $565,000

    Pending
    • 5 Beds
    • 3 Baths
    • 2,970 Sq Ft

    745 Feather Sound Dr, Bolingbrook, IL 60440

    Discover Modern Luxury in Feather Sound Welcome to this impeccably maintained 5-bedroom, 3-bath gem nestled in the highly sought-after Feather Sound subdivision of Bolingbrook. Combining high-end upgrades with thoughtful outdoor design, this home offers a perfect blend of style, security, and functionality. Interior Highlights Modern Kitchen: A chef's delight featuring newer appliances, including

    Sean Cochran eXp Realty

    745 Feather Sound Dr, Bolingbrook, IL 60440
  • /47

    $519,000

    Pending
    • 4 Beds
    • 4 Baths
    • 2,332 Sq Ft

    663 Anne Ln, Bolingbrook, IL 60440

    This well-maintained home features a beautiful brick front, offering timeless curb appeal and low-maintenance living. Step inside to a bright and inviting interior featuring a functional layout perfect for both everyday living and entertaining. The spacious living areas are filled with natural light, creating a warm and welcoming atmosphere. The kitchen offers plenty of cabinet and counter space

    Kate Seemann Redfin Corporation

    663 Anne Ln, 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
  • /23

    $299,900

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

    524 Monroe Rd, Bolingbrook, IL 60440

    Welcome to your new home! This 3 bedroom, 2.1 bath with a full finished basement, END UNIT HOME. Freshly painted, light and bright. This home boasts new appliances '23, canned lighting in large country kitchen with a pantry closet for great storage. Open floor plan Living and Dining room is great for entertaining. Thermo windows with slider to a fenced back yard w/storage unit that stays. Patio

    Josie DeRiggi Coldwell Banker Realty

    524 Monroe Rd, Bolingbrook, IL 60440
  • /58

    $999,999

    • 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
  • /48

    $444,900

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,506 Sq Ft

    424 Assembly Dr, Bolingbrook, IL 60440

    Step inside through the impressive double front doors and into a modern, inviting family room that sets the tone for this beautifully laid-out home. From the moment you enter, you're greeted by a stunning vaulted ceiling spanning the formal living and dining rooms. The living room features a sleek fireplace style heater, gleaming hardwood floors, and a large picture window that fills the space

    Ralph Binetti RE/MAX Suburban

    424 Assembly Dr, Bolingbrook, IL 60440
  • /21

    $350,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 1,905 Sq Ft

    3 Revere Ct, Bolingbrook, IL 60440

    Welcome to 3 Revere Ct in Bolingbrook, an inviting, move-in-ready home perfectly situated on a quiet cul-de-sac in the desirable Winston Woods subdivision. Step inside to a sun drenched living room that flows seamlessly into a separate dining area, creating an ideal layout for both everyday living and entertaining. The updated kitchen features granite countertops, rich mocha cabinetry, stainless

    Moin Haque Coldwell Banker Realty

    3 Revere Ct, 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
  • /31

    $435,000

    $10K PRICE DROP
    • 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 offers three spacious bedrooms and two full baths on the main level, plus a fully finished lower level with a half bath-providing flexible living space ideal for a family room, home office, or potential fourth bedroom.The bright, open living room has beautiful hardwood floors

    Sheryl Long Village Realty, Inc.

    417 Cambridge Way, Bolingbrook, IL 60440
  • /28

    $284,900

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

    166 Tracy Way, Bolingbrook, IL 60440

    Welcome to 166 Tracy Way in Bolingbrook - a beautifully refreshed home ready for its next owner! This move-in ready property features brand new appliances, stylish new flooring throughout, fresh paint that gives the entire home a clean, modern feel, new bathrooms and so much more! Bright and inviting living spaces offer comfort and functionality, while the updated finishes make everyday living

    Joseph Mueller Tanis Group Realty

    166 Tracy Way, Bolingbrook, IL 60440
  • /25

    $220,000

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

    149 Thomas Rd, Bolingbrook, IL 60440

    Multiple offers received. RENTALS ALLOWED VALUE-ADD OPPORTUNITY! Unlock instant equity in this spacious 2+1BR, 2.5BA Bolingbrook townhome. Freshly painted (2025) and new carpet (2025) provide a clean, modern canvas to start your renovation journey. The Heavy Lifting Started: New Garage Door (2023), Smart Thermostat (2024), Stove (2020), Water Heater (2018), and Roof (~7 yrs). The Canvas: Original

    Daniel Firks Coldwell Banker Real Estate Group

    149 Thomas Rd, Bolingbrook, IL 60440
  • /43

    $399,900

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

    418 Charlestown Dr, Bolingbrook, IL 60440

    Move right in to this beautifully maintained home with wonderful curb appeal and a professionally landscaped yard. This bright and inviting home has been thoughtfully updated throughout and features a stunning custom staircase, low-maintenance flooring, and an updated kitchen with modern finishes and abundant cabinet space. Fresh paint and new carpet create a crisp, move-in-ready feel. The

    Francine Caliendo RE/MAX of Naperville

    418 Charlestown Dr, Bolingbrook, IL 60440
  • /22

    $269,000

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

    140 Leslie Ln Unit 3, Bolingbrook, IL 60440

    Well cared for townhouse in Winston Village is close to everything Bolingbrook has to offer. It features 2 bedrooms and 2 baths and a first-floor den/office and first-floor 1/2 bath. Primary suite is large with walk in closet and private full bath. This home has a well-equipped kitchen with a pantry closet, stainless steel appliances and an additional cabinet that could be used as a coffee bar.

    Jody Coari Century 21 Circle

    140 Leslie Ln Unit 3, Bolingbrook, IL 60440
  • /19

    $249,900

    • 4 Beds
    • 2.5 Baths
    • 2,136 Sq Ft

    157 Thomas Rd Unit 157, Bolingbrook, IL 60440

    Spacious and well-maintained 2-story townhome located in the heart of Bolingbrook! This inviting residence offers a functional layout with generous living spaces, abundant natural light, and plenty of room for everyday living and entertaining. The main level features a bright and comfortable living area, a spacious kitchen with ample cabinetry and countertop space, and a dining area overlooking

    Ryan Ivemeyer O'Neil Property Group, LLC

    157 Thomas Rd Unit 157, Bolingbrook, IL 60440
  • /16

    $350,000

    Open Sun 1PM - 3:30PM
    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    427 Devon Ln, Bolingbrook, IL 60440

    SHORT SALE APPROVED AT LIST PRICE! Incredible opportunity for investors, rehabbers, or savvy buyers looking to build instant equity. This spacious home features a newer roof and newer siding, providing a solid foundation for your finishing touches. With only minor TLC needed, this property can quickly be restored to its full potential. Inside, you'll find granite countertops, stainless steel

    Nafis Noorali AAA Real Estate

    427 Devon Ln, Bolingbrook, IL 60440
  • /34

    $439,900

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

    602 N Ashbury Ave, Bolingbrook, IL 60440

    Welcome to this beautifully updated 5-bedroom, 3-bath raised ranch in the highly sought-after Winston Woods subdivision of Bolingbrook! Situated on a spacious fenced lot with mature trees, this home offers the perfect blend of modern updates, functional living space, and inviting indoor-outdoor living. Step inside to find a bright and spacious layout featuring updated flooring, updated fixtures,

    Ajrije Gazafer Kale Realty

    602 N Ashbury Ave, Bolingbrook, IL 60440
  • /11

    $360,000

    Pending
    • 3 Beds
    • 3 Baths
    • 1,434 Sq Ft

    614 Feather Sound Dr, Bolingbrook, IL 60440

    MULTIPLE OFFERS RECEIVED-SELLER IS CALLING FOR HIGHEST AND BEST BY Wednesday 5/27/26 no later than 5pm. Unique brick home for sale in Bolingbrook, conveniently located within walking distance to the Bolingbrook Promenade shopping, dining, and entertainment district. This spacious home has been completely cleared out following the estate sale, professionally cleaned, and is ready for its next

    Darlene Mahnke United Real Estate - Chicago

    614 Feather Sound Dr, Bolingbrook, IL 60440
  • /21

    $235,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,180 Sq Ft

    585 Sharon Way, Bolingbrook, IL 60440

    ***Multiple Offers. Offer Deadline Wednesday May 13th at 7pm CT*** Don't Miss This Meticulously Maintained 3 Bed | 1.1-Bath Turnkey Townhome in the Highly Sought After Winston Village Subdivision in Bolingbrook - Fully Renovated in 2020 & Loaded w/ Updates That Give the Next Owner True Peace of Mind! Whether You're Looking for a Primary Residence or a Ready-to-Rent Investment Property, this Home

    Ryan Widerberg eXp Realty - Chicago North Ave

    585 Sharon Way, Bolingbrook, IL 60440
  • /16

    $360,000

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

    406 Assembly Dr, Bolingbrook, IL 60440

    Your dream home is here! This spacious 4-bedroom, 2.1-bath property offers 1,915 sq. ft. of bright, open living space designed for comfort and style. From the welcoming living room and formal dining area to the cozy family room perfect for entertaining, this home has it all. The kitchen provides plenty of storage and flows effortlessly into the main living spaces-ideal for hosting family and

    Felicia Holmes Coldwell Banker Realty

    406 Assembly Dr, Bolingbrook, IL 60440

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 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 $375,000. If you put a 20% down payment of $75,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $1,860 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $80K 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, Whalon Lake, South Woodridge and Hawthorne Hill.

Home Trends in Winston Woods, IL

Housing Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$380,000
Median Townhouse Sale Price
$262,400
Average Price Per Sq Ft
$191
Number of Homes for Sale
5
Last 12 months Home Sales
67
Months of Supply
0.90
Median List Price
$375,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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