$373,475Average Value$192Average Price per Sq Ft11Homes For Sale
Accessible-living in southwestern Chicago
Bolingbrook is known for its park districts, and Winston Woods is no exception, blending outdoor recreation and nearby urban amenities for the perfect suburban lifestyle. Residents here take advantage of their proximity to both outdoor and urban amenities. From fishing at Gateway Wetlands Park to hiking at Winston Woods Park — where the name of the community originates from. And The Promenade Bolingbrook shopping mall is adjacent to the community, offering immediate access to an elevated shopping experience. “The location is what makes Winston Woods special — The community borders Winston Woods Park and offers immediate access to the 355 and 55, two major highways within the area,” says long-time local Kayla Rembert, Realtor with Rembert Blount Property Group at Keller Williams Infinity. And with a quick 30-mile commute into downtown Chicago, residents can make a day trip to the windy city in about an hour.
Shopping at The Promenade Bolingbrook
Residents here can shop at The Promenade Bolingbrook, which offers department stores and retailers, like Macy’s, Barnes and Noble and DSW Designer Shoe Warehouse. Groceries and everyday essentials can be found nearby at stores like Costco, Meijer and Aldi. When dining in the area, locals can visit Wholey Granoly for their house-made juices, smoothies and a wide variety of vegan breakfast and lunch options. For authentic Mexican cuisine, head to Taquería El Valle for their quesabirria tacos and hand-made tortillas. Or check out Danny's Pizza and Burger Bar for a wide selection of craft beers, American classics and their famous Farmer Jack Burger.
The Promenade Bolingbrook, is a 750,000-square-foot open-air shopping center.
Danny's Pizza and Burger Bar features American classics with a variety of beers on tap.
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Wednesday Night Summer Concert Series
Every summer, the Bolingbrook Park District hosts free live music and entertainment every Wednesday night starting at 7:30 pm to 9:00 pm from the end of May through September. The concerts are hosted at the Bolingbrook Performing Art Center off Briarcliff Road. Visitors are encouraged to bring low-backed lawn chairs and blankets as seating will not be provided.
During the summer families love attending the Wednesday Night Concert Series.
Music lovers of all ages enjoying the Wednesday Night Summer Concerts in Bolingbrook, IL.
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Colonial Revivals and traditional ramblers
Wide streets lined with elm trees pave the way for residents with sidewalks for added safety when strolling through the community. Winston Woods offers a variety of home styles from traditional Ranch-styles and Colonial Revivals to bi-level homes and multi-family townhouses. With a median sales price of $280,000, homes range from the high $100,000s for a three-bedroom townhouse to upwards of $600,000 for a four-bedroom Colonial Revival. “There are many long-term residents in Winston Woods, however it does attract Chicago commuters and young families with its mid-sized starter homes,” says Rembert, Creator of “From The Skyline To The Suburbs” YouTube channel. While single family homes dominate the area, multi-family townhouses are also available on the western side of Winston Woods along North Bolingbrook Drive. Winston Woods features subdivision options from those bordering Winston Woods Park in Winston Woods to those that surround the Gateway Wetlands in Feathersound and multi-family townhouses in communities like Winston Village. Homes here often feature attached garages and are typically fronted by wide paved driveways and mid-sized yards large enough for shrubbery and a few trees.
Winston Woods features pampered lawns with neatly trimmed hedges.
A common architectural style in Winston Woods is split-level.
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Education at Valley View Community Schools
Students in Winston Woods can attend schools like Wood View Elementary, Brooks Middle and Bolingbrook High School, which respectively received ratings of C-plus, B-plus and A-minus from the educational review site, Niche. Wood View Elementary School hosts field days every semester for students to stay active and participate in a variety of outdoor activities. Brooks Middle School serves over 900 students and boasts a student-teacher ratio of 12:1. Bolingbrook High School offers a rigorous curriculum with 12 Advanced Placement (AP) courses for higher education preparation. Private options like St. Scholastica Elementary School are also common here.
Educational opportunities abound at Wood View Elementary.
Residents of Winston Woods can send their kids to Bolingbrook High School.
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Launch an arrow at Chicago Bow Hunters
When seeking time outdoors, residents can explore the trails and natural scenery at Winston Woods Park, or shoot a bullseye at Chicago Bow Hunters on the eastern side of the park. Or checkout Gateway Wetlands Park for 51 acres of paved hiking paths around the pond or fishing off the wooden docks. Golf enthusiasts can book a session at Mistwood Golf Dome for fine-tuning the perfect swing on their indoor driving range, golf simulator suite or at their lessons. Friends and family can reserve a suite and enjoy golfing and bar bites from the sports bar. During the summer months, local residents can sunbathe or cool off at Cypress Cove Family Aquatic Park, which offers a six-lane pool, three water slides and a beach perfect for building sand castles. The park is open from early June until the end of August, offering seasonal memberships and discounts to homeowners in the Cypress Cove area.
Winston Woods Park is a great place to get away from it all.
The Chicago Bow Hunters archery club was founded in 1939.
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Nearby healthcare and transportation around Winston Woods
Residents here rely on North Bolingbrook Drive and U.S. Interstate 355 for easy access into Bolingbrook and neighboring areas like Woodbridge and Whalon Lake. When seeking public transportation, locals can hop on the Pace Suburban Bus, which operates along North Bolingbrook Dr. Or head to Lemont for the closest Metra station. The Chicago Midway International Airport is 23 miles from Winston Woods when traveling further outside the community. For healthcare, the UChicago Medicine AdventHealth Bolingbrook is only 4 miles from Winston Woods.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Winston Woods neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Winston Woods
US
Homicide
1
4
Sexual Assault
4
4
Assault with Weapon
3
4
Robbery
4
4
Burglary
3
4
Motor Vehicle Theft
3
4
Larceny
3
4
Crime Score
3
4
Source: WhatIsMyCrimeRisk.com
Winston Woods Demographics and Home Trends
On average, homes in Winston Woods, Bolingbrook sell after 21 days on the market compared to the national average of 56 days. The median sale price for homes in Winston Woods, Bolingbrook over the last 12 months is $360,000, down 3% from the median home sale price over the previous 12 months.
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
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
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
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
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,
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,
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
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
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
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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