Winston Woods
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.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.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.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.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.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.


Agents Specializing in this Area
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Angela Walker
Angela Walker Homes Real Estate Group
(708) 300-9563
177 Total Sales
2 in Winston Woods
$315K - $375K Price Range
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Shena Omotola
Skyward Realty
(219) 351-6993
47 Total Sales
1 in Winston Woods
$229,000 Price
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Carrie Clements
Baird & Warner
(224) 808-4249
62 Total Sales
1 in Winston Woods
$540,000 Price
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June Kim
Responds QuicklyLegacy Properties, A Sarah Leonard Company, LLC
(224) 479-1566
139 Total Sales
1 in Winston Woods
$380,000 Price
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Jaeh Korwitts
Compass
(630) 756-5654
101 Total Sales
1 in Winston Woods
$366,750 Price
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Christine Fischer
RE/MAX 1st Service
(708) 274-4213
58 Total Sales
1 in Winston Woods
$68,000 Price
Schools
Interested in learning more about homes in this area? Reach out to
, an experienced agent in this neighborhood.Parks in this Area
Transit
Crime and Safety
1 - Low Crime, 10 - High Crime | Winston Woods | US |
---|---|---|
Homicide | 3 | 4 |
Sexual Assault | 3 | 4 |
Assault with Weapon | 3 | 4 |
Robbery | 3 | 4 |
Burglary | 2 | 4 |
Motor Vehicle Theft | 3 | 4 |
Larceny | 2 | 4 |
Crime Score | 3 | 4 |
Source: WhatIsMyCrimeRisk.com
Winston Woods Demographics and Home Trends
On average, homes in Winston Woods, Bolingbrook sell after 38 days on the market compared to the national average of 70 days. The median sale price for homes in Winston Woods, Bolingbrook over the last 12 months is $505,000, down 17% from the median home sale price over the previous 12 months.
Housing Trends
Neighborhood Facts
Distribution of Home Values
Homes for Sale
Homes for Rent
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, an experienced agent in this neighborhood.Average Home Value
Property Mix - Square Feet
This Neighborhood Has More Owners
Demographics
Finances
Education and Workforce
Weather
Area Factors
Bikeable
Bike Score®
Somewhat Walkable
Walk Score®
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
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