Wheeling · Cook County · IL
Homes for sale in
Hollywood Ridge.
- Active listings
- 0
- Median list
- $0
- Avg time on market
- 0 days
- Sold · last year
- 10
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About the community
An established mid-century neighborhood on Wheeling's west side.
Hollywood Ridge is a single-family neighborhood on the west side of Wheeling in Cook County, developed primarily through the 1960s into the early 1970s during the region's postwar expansion. Today it presents as a mature, tree-lined area rather than a new-construction community, with a distinctly mid-century street grid (Beverly, Wilshire, Woodland, Valley Stream) that gives the neighborhood its Hollywood name and identity. The housing stock runs from modest ranches to larger split-levels and two-stories, and it is one of the more attainable ways into Wheeling and the well-regarded Township High School District 214.
At a glance
Mid-century homes
Detached single-family ranches, split-levels, and two-stories built largely in the 1960s and early 1970s.
Attainable entry point
One of the more accessible pockets of the north and northwest suburbs for detached homes.
No mandatory HOA
An established subdivision of individually owned lots with no governing association dues on record.
Mature, tree-lined streets
Curbs, sidewalks, and street lights throughout a settled, owner-occupied neighborhood.
Metra North Central Line
The Wheeling station offers weekday service toward Chicago Union Station.
Milwaukee Avenue dining
Wheeling's Restaurant Row is a short drive away.
District 21 and District 214
Wheeling CCSD 21 for elementary and middle, Township High School District 214 for high school.
What’s close
Hollywood Ridge sits in west Wheeling near Dundee Road (Route 68), close to Route 83, with everyday retail and the Metra station a short drive away.
- Shopping
- A shopping center anchors the Dundee Road and Route 83 area, with more retail along Milwaukee Avenue.
- Hospital
- Northwest Community Healthcare (Endeavor Health) in Arlington Heights is the nearest major hospital.
- Highway
- Quick connections to I-294 (Tri-State) and I-94, with Route 83 and Lake-Cook Road as major surface routes.
- Train
- Metra North Central Line at the Wheeling station for weekday service to Union Station.
- Airport
- O'Hare is roughly 16 miles south, and Chicago Executive Airport (general aviation) is in Wheeling.
- Schools
- Wheeling CCSD 21 and Township High School District 214. Specific school assignment varies by address and should be confirmed.
What it’s actually like to live here
Hollywood Ridge suits buyers who want an established, unpretentious Cook County suburb rather than a shiny new subdivision. The homes are mid-century, the trees are mature, and the streets are quiet and residential. It is one of the more attainable ways into Wheeling and the District 214 high school system, which makes it a natural fit for first-time buyers, right-sizers, and families who prioritize location and value over square footage. The commuter math is a real selling point, with the Metra North Central Line, Dundee Road, Route 83, and the tollway network all close, and both O'Hare and Chicago Executive Airport a short drive.
The honest tradeoffs are the tradeoffs of any 1960s-era neighborhood. Original homes may carry dated kitchens, baths, and mechanical systems, so budget for updates and inspect for the usual older-home items such as electrical service, sewer line, roof, and windows. Square footage skews modest by today's standards, and layouts reflect the era. As with all of Cook County, property taxes are meaningful and should be underwritten carefully rather than assumed.
The upside is stability and connection. This is a settled, owner-occupied pocket of Wheeling with everyday retail at Dundee and Route 83, Wheeling Park District recreation nearby, and Milwaukee Avenue's dining scene minutes away. Buyers who value a proven location and are comfortable putting some sweat equity into a solid older home tend to be the happiest here.
The questions buyers actually ask
Hollywood Ridge FAQ
The questions I get most from buyers shopping Hollywood Ridge. If yours isn't here, text 224-385-8779, same-day reply.
- What are property taxes like?
- Roughly $7,000 – $11,000 per year, depending on home size and value. Cook County assessor records are the source of truth. Happy to pull a specific bill on any home you're considering.
- 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.
- What kind of homes are in Hollywood Ridge?
- Mostly detached single-family homes built primarily in the 1960s into the early 1970s, generally 3 to 5 bedrooms, ranging from compact ranches to larger split-levels and two-stories. Expect mid-century construction and, in many cases, room to update.
- Is there an HOA?
- No mandatory homeowners association is on record, and listing data shows the association fee as $0. Confirm on any specific property whether minor voluntary dues or a special service area apply.
- Which schools would my kids attend?
- Elementary and middle grades fall under Wheeling CCSD 21 and high school under Township High School District 214. The exact assigned schools vary by address and more than one school appears in the data, so confirm the current boundary directly with the districts for the specific home.
- How is the commute to Chicago and O'Hare?
- Strong. Metra's North Central Line runs from the Wheeling station toward downtown on weekdays, Dundee Road and Route 83 give quick surface access, I-294 and I-94 are close, and O'Hare is about 16 miles south. Chicago Executive Airport is right in Wheeling for general aviation.
- What do homes cost and how is the market right now?
- Pricing moves with the market, so rather than quote a number, see the live Market snapshot on this page for current list prices, recent sales, and activity. In general terms, Hollywood Ridge is one of the more attainable, mid-market entry points in the Wheeling area.
- What should I watch out for in an older home here?
- The usual older-home items. Have the electrical service, plumbing and sewer line, roof, windows, and HVAC inspected, and budget for cosmetic and mechanical updates. Also underwrite the Cook County property tax bill carefully, since effective rates in the area are meaningful.
- Who is the real estate agent for Hollywood Ridge?
- Joe Keegan is the local licensed Illinois real estate broker who covers Hollywood Ridge in Wheeling, 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 Hollywood Ridge 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 Hollywood Ridge
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
- Wheeling specialist
- Honest local market take
- Brokerocity
Market snapshot
Hollywood Ridge, 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 sale price · last 90 days
$385,000
Sold in the last year
10
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.
Thinking of selling?
What's your home actually worth?
Not a Zestimate. A real CMA from someone who's sold this neighborhood, knows the floor plan premiums, and can tell you which upgrades the buyer pool here actually pays for.
- Pricing range with comp-by-comp logic
- Pre-list improvements that pay back, and the ones that don't
- No obligation, no spam, no auto-dialer
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