Woodridge · DuPage County · IL
Homes for sale in
Winston Hills.
- Active listings
- 3
- Median list
- $525K
- Avg time on market
- 25 days
- Sold · last year
- 34
Active listings
3 homes on the market
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About the community
An established, centrally located DuPage subdivision with easy tollway access.
Winston Hills is one of the subdivisions that built early Woodridge. Winston-Muss Builders started it in 1964, and per the village's own history it added roughly 5,000 residents as it filled in, helping push Woodridge past 11,000 people by 1970. It sits on the north side of Woodridge near Roberts Drive, and it is a mix of single-family homes with a pocket of condominiums. Core construction ran through the 1960s and 1970s with later infill, so it reads as a mature, tree-lined, mid-century neighborhood rather than a new-construction or luxury enclave. The draw is location, space, and relative affordability with I-355 and I-55 both close.
At a glance
Single-family plus condos
Detached homes roughly 1,100 to 3,300 sq ft, plus a condominium component that keeps an affordable entry point.
Built from 1964
Started by Winston-Muss Builders in 1964, with most homes from the 1960s and 1970s and some later infill.
Woodridge District 68
Elementary and junior high in Woodridge School District 68, with Thomas Jefferson Junior High for grades 7 to 8. Confirm the assigned elementary by address.
High school in District 99
Community High School District 99, either Downers Grove North or Downers Grove South depending on the address.
Cypress Cove waterpark
The Woodridge Park District's bayou-themed aquatic park, with a lazy river and slides, is a neighborhood recreation anchor.
I-355 and I-55 access
Woodridge sits at the crossroads of both tollways, roughly 25 miles southwest of downtown Chicago.
Seven Bridges nearby
The Seven Bridges retail, dining, and entertainment center in Woodridge is a short drive away.
What’s close
Winston Hills sits on the north side of Woodridge near Roberts Drive, with I-355 and I-55 both a short drive and the BNSF Metra stations in nearby towns.
- Recreation
- The Woodridge Park District, including the Cypress Cove aquatic park and neighborhood parks and the Athletic Recreation Center.
- Shopping
- Seven Bridges in Woodridge, plus Target, Jewel-Osco, and the retail corridors of Downers Grove and Darien.
- Hospital
- Advocate Good Samaritan Hospital in adjacent Downers Grove.
- Highway
- I-355 (Veterans Memorial Tollway) and I-55 (Stevenson Expressway), both close by.
- Schools
- Woodridge School District 68 for K to 8 and Community High School District 99 for high school. Confirm assignment by address.
- Train
- No Metra station in Woodridge, so rail commuters use the BNSF line at nearby Lisle or the Downers Grove area into Union Station.
What it’s actually like to live here
Winston Hills is a quintessential established DuPage suburb: mature trees, curb-and-gutter streets, and a mix of 1960s and 1970s single-family homes with a pocket of condominiums that keeps an entry point affordable. It appeals to buyers who want a real yard and quick expressway access without paying newer-construction prices. The single-family homes give first-time and move-up buyers room to grow, while the condos offer some of the lowest cost-of-entry housing in the Woodridge market.
Daily life is convenient and car-oriented. I-355 and I-55 are both close, so the northwest and southwest suburbs, the job corridors, and O'Hare are straightforward drives, and Seven Bridges covers shopping, dining, and a movie night without going far. Recreation leans on a strong Woodridge Park District, headlined by the Cypress Cove waterpark, so families are not dependent on a private HOA amenity package.
The honest tradeoffs are worth stating plainly. The housing stock is older, so buyers should inspect and budget for aging roofs, HVAC, windows, and in some homes original kitchens and baths, and value here often comes from updated versus dated interiors. DuPage County property taxes are high relative to the national average, so the annual tax bill is a real line item to underwrite up front. And there is no in-town Metra station, so rail commuters drive to Lisle or the Downers Grove stations, which adds a park-and-ride step compared with a true walk-to-train town.
The questions buyers actually ask
Winston Hills FAQ
The questions I get most from buyers shopping Winston Hills. If yours isn't here, text 224-385-8779, same-day reply.
- What does the HOA actually cover?
- Most detached single-family homes in Winston Hills are not in a mandatory homeowners association, which is typical of Woodridge's 1960s and 1970s tracts. The condominium buildings within the neighborhood have their own associations, with monthly assessments recently reported roughly $335 to $500 that cover building exterior and grounds, insurance on the structure, and reserves. Confirm the specific association and dues for any attached unit.
- What are property taxes like?
- Roughly $7,000 – $9,000 per year, depending on home size and value. DuPage County assessor records are the source of truth. Happy to pull a specific bill on any home you're considering.
- When was Winston Hills built?
- Winston-Muss Builders (original developer, from 1964) built the community between 1964 and 2003. Winston-Muss Builders (original developer, from 1964) stopped new construction in 2003, so every sale today is a resale.
- What's the typical closing timeline?
- 30 to 60 days from accepted offer to keys. Cash deals can close in two weeks. Conventional financing is usually closer to 60.
- When was Winston Hills built and who developed it?
- It was started in 1964 by Winston-Muss Builders, with most homes dating to the 1960s and 1970s and some later infill through the early 2000s. It was one of the subdivisions that grew early Woodridge, adding roughly 5,000 residents to the village.
- Is there an HOA and what does it cost?
- The single-family homes generally have no mandatory HOA. The condominium buildings have their own associations with monthly assessments recently reported roughly $335 to $500. Confirm the exact association, dues, and what they cover for the specific unit.
- What schools serve Winston Hills?
- Elementary and junior high are in Woodridge School District 68, with Thomas Jefferson Junior High for grades 7 and 8. High school is Community High School District 99, either Downers Grove North or Downers Grove South. Exact building assignment depends on the address, so verify on the District 68 and District 99 boundary maps before you buy.
- What do homes cost?
- Recently, single-family homes have generally listed in the $400,000s to high $500,000s, and condos in roughly the $185,000 to $205,000 range, with a neighborhood median sale price near $410,000. Market conditions shift, so confirm current comps.
- How are the property taxes?
- Expect a DuPage County tax load. Effective rates in Woodridge run roughly 2.0 to 2.5 percent of value, so budget somewhere in the range of $7,000 to $9,000 a year on a mid-priced single-family home, with the exact bill driven by assessed value and exemptions. Pull the actual PIN bill from the DuPage County Treasurer before relying on a number.
- How is the commute and location?
- Very convenient by car: I-355 and I-55 are both close, and downtown Chicago is about 25 miles northeast. There is no Metra station in Woodridge itself, so train commuters use nearby BNSF stations in Lisle or the Downers Grove area. Seven Bridges shopping and Advocate Good Samaritan Hospital are close by.
- Who is the real estate agent for Winston Hills?
- Joe Keegan is the local licensed Illinois real estate broker who covers Winston Hills in Woodridge, IL through Subdiview, a neighborhood-first home search for the Chicago suburbs and collar counties. Joe prices and negotiates from the live MRED sold comps for Winston Hills specifically, not national averages, and can help you buy or sell here. Reach Joe at 224-385-8779 or joe@joekeeganhomes.com.
Your local agent
Joe knows Winston Hills
Most agents will list anything. I focus on the places I actually know, and the things that move value here don't show up in the MLS write-up: which streets and buildings hold demand, what the HOA or assessments really cover, how the comps read once you account for condition and location, and where buyers consistently want to be.
When you're ready to tour or list, you want someone who has read the last 50 closed comps in this specific market, not a national average, and can tell you what they actually mean for your price. That's how I work. Text or call any time, and I'll give you a real take, not a brochure.
- Licensed Illinois broker
- Comp-driven pricing
- Woodridge specialist
- Honest local market take
- Brokerocity
Market snapshot
Winston Hills, by the numbers
Live MRED data, refreshed daily. The numbers below tell you what this market is doing today, not what Zillow's algorithm thinks it might be doing six weeks from now.
Typical list price
$525,000
Typical sale price · last 90 days
$420,000
Homes for sale right now
3
Avg time on market
25 days
Sold in the last year
34
This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC for the period August 1, 2025 through August 1, 2026. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.
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Schools serving Winston Hills
Where Winston Hills homes go to school
Homes in Winston Hills are most often zoned to Downers Grove North HS. Open a school to see its area, the district, and every home for sale that feeds it.
School assignment is derived from the school the MRED listing agent entered and is not a guarantee. Always verify current attendance boundaries with the district before writing an offer.
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