Waukegan · Lake County · IL
Homes for sale in
Pleasant Hill.
- Active listings
- 1
- Median list
- $369K
- Avg time on market
- 42 days
- Sold · last year
- 8
Active listings
1 home on the market
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About the community
An attainable, established southwest-Waukegan neighborhood.
Pleasant Hill is a planned residential community on the far southwest side of Waukegan, in Lake County, clustered around O'Plaine Road near the Gurnee border. It was developed by Town & Country Homes and built out primarily from the mid-1990s into the early 2000s, pairing detached single-family homes with an adjacent townhome section. In character it is a quiet, established, owner-occupied neighborhood of curving streets, sidewalks, and mature landscaping, with a diverse, family-oriented resident base. There is one geographic quirk that drives much of this page: despite the Waukegan mailing address, this pocket sits in the Gurnee-based school districts, not the Waukegan city district.
At a glance
Town & Country homes
Detached single-family homes plus an adjacent townhome section, built mid-1990s into the early 2000s.
Gurnee school districts
Woodland CCSD 50 (K-8) and Warren Township HSD 121 (9-12), not Waukegan 60; confirm by address.
Attainable tier
One of the more accessible single-family options in the area, mid-tier for Lake County.
I-94 and Route 41
Quick access to the two main north-south routes between Chicago and Wisconsin.
Gurnee Mills nearby
The large Gurnee Mills outlet center and the Grand Avenue retail corridor are a short drive west.
Six Flags close
Six Flags Great America and Hurricane Harbor are nearby in Gurnee.
UP-North Metra
The Waukegan station on the Union Pacific North line runs to Ogilvie in downtown Chicago.
HOA in place
A single-family association maintains common areas and appearance; townhomes carry a separate assessment.
What’s close
Pleasant Hill sits on the far southwest side of Waukegan near O'Plaine Road and the Gurnee border, with I-94 and Route 41 the main commuter routes.
- Highway
- Interstate 94 and U.S. Route 41 for north-south travel; Route 132 (Grand Avenue) and Route 120 for east-west.
- Train
- Metra Union Pacific North line from the Waukegan station to Ogilvie Transportation Center, roughly 36 rail miles downtown.
- Shopping
- Gurnee Mills, one of the largest outlet centers in Illinois, plus big-box and everyday retail along the Grand Avenue corridor.
- Recreation
- Six Flags Great America and Hurricane Harbor in Gurnee, plus Lake County forest preserves and Lake Michigan nearby.
- Schools
- Woodland CCSD 50 for K-8 and Warren Township HSD 121 for high school; confirm by address, as the district line runs through this area.
- Setting
- Roughly midway between Chicago and Milwaukee, about a 40-minute drive to each.
What it’s actually like to live here
Pleasant Hill reads as a settled, unpretentious suburban neighborhood built for everyday family life rather than for show. The streets curve gently, the sidewalks connect, and two decades of tree growth have softened what was once raw production construction into a lived-in, green setting. The mix of detached houses and attached townhomes gives the community a range of entry points, which is a big part of why it stays attainable and mid-tier for Lake County and why it draws a genuinely diverse set of neighbors, from first-time buyers to families trading up.
Location is the quiet superpower here. You are minutes from I-94 and Route 41, a manageable drive to the Waukegan Metra station for a car-free run into downtown Chicago, and close enough to Gurnee Mills, the Grand Avenue retail strip, and Six Flags that errands and weekend outings barely register as trips. The single-family HOA and the townhome association keep the common areas and the neighborhood's overall appearance in order, which helps the community hold its character over time.
The honest tradeoffs are worth stating plainly. This is Waukegan, and Lake County property taxes are high, so the effective tax rate deserves close attention when you run the numbers. The single biggest thing to verify is schools: the Waukegan mailing address does not mean Waukegan city schools here, and because a district boundary runs through this part of town, school assignment must be confirmed for the exact address rather than assumed. This is a residential subdivision, not an amenity-loaded master plan, so calibrate expectations toward a solid neighborhood rather than a resort community.
The questions buyers actually ask
Pleasant Hill FAQ
The questions I get most from buyers shopping Pleasant Hill. If yours isn't here, text 224-385-8779, same-day reply.
- What does the HOA actually cover?
- Pleasant Hill has a dedicated single-family homeowners association that handles common-area maintenance and improvement, covenant and appearance control, insurance on common areas, and assessment administration. The attached-townhome component typically carries its own separate, higher assessment that usually covers exterior upkeep, landscaping, and snow removal. Always request the current dues, budget, and governing documents for the exact home, since single-family and townhome obligations differ.
- When was Pleasant Hill built?
- Town & Country Homes built the community between 1994 and 2002. Town & Country Homes stopped new construction in 2002, 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.
- Who built Pleasant Hill and when?
- It was developed by Town & Country Homes, a large Chicago-area production builder, and built out mainly from the mid-1990s into the early 2000s. It includes both detached single-family homes and an attached townhome section.
- Which school district is Pleasant Hill in? Is it Waukegan schools?
- Despite the Waukegan mailing address, real-estate data assign this subdivision to the Gurnee-based districts: Woodland CCSD 50 for K-8 and Warren Township High School District 121 for grades 9-12, not Waukegan CUSD 60. Because a district boundary runs through this part of west Waukegan, confirm the assigned district and schools for the specific address before relying on it. This is the single most important thing to verify here.
- Is there an HOA, and what does it cover?
- Yes. A dedicated single-family homeowners association handles common-area maintenance and improvement, covenant and appearance control, insurance on common areas, and assessment administration. The attached-townhome component typically has its own separate, higher assessment that usually covers exterior upkeep, landscaping, and snow removal. Always request the current dues, budget, and documents for the exact home.
- What do homes cost and how is the market right now?
- Pleasant Hill is generally attainable and mid-tier for Lake County, which is part of its appeal. For current, accurate numbers on active prices, recent sales, and how quickly homes are selling, see the live Market snapshot on this page, which pulls directly from the MLS.
- What size and style of homes are here?
- A mix of two-story and some ranch-style production floor plans from Town & Country Homes, generally three to five bedrooms in the single-family homes and two to three in the attached homes, ranging from smaller townhome models up to the larger single-family plans.
- How is the commute and what is nearby?
- Access is a strength: I-94 and Route 41 are close for driving, and the Metra Union Pacific North line runs from the Waukegan station into downtown Chicago. Gurnee Mills, the Grand Avenue retail corridor, Six Flags Great America, area hospitals, and Lake County forest preserves are all a short drive away.
- Who is the real estate agent for Pleasant Hill?
- Joe Keegan is the local licensed Illinois real estate broker who covers Pleasant Hill in Waukegan, 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 Pleasant Hill 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 Pleasant Hill
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
- Waukegan specialist
- Honest local market take
- Brokerocity
Market snapshot
Pleasant Hill, 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
$369,000
Typical sale price · last 90 days
$295,000
Homes for sale right now
1
Avg time on market
42 days
Sold in the last year
8
This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC for the period September 10, 2025 through September 10, 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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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.
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Schools serving Pleasant Hill
Where Pleasant Hill homes go to school
Homes in Pleasant Hill are most often zoned to Warren Township 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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