Residential and commercial roofing in Highland Park since 1996. Roof replacement, roof repair, hail and storm damage, cedar shake alternatives, slate and copper work, flat roofing for commercial buildings. Family-owned, IL licensed (#104.010248), based in Mount Prospect — local crew, year-round availability.
Architectural shingle, designer shingle, cedar shake alternatives, slate, and copper. Pricing ranges from $40K for standard architectural up to $300K+ for natural slate with full copper scope on lakefront and Ravinia estates.
Storm damage, leaks, missing shingles, flashing failures, ice dam damage. Most repairs run $1.5K–$8K. We give an honest assessment — if your roof needs replacement instead of repair, we'll tell you.
Free roof inspections for Highland Park homeowners — including post-storm assessments and pre-listing condition reports. Written report with photos. We document what's there, not what we want to sell you.
TPO, EPDM, modified bitumen, and silicone coatings for Park Avenue corridor buildings, professional offices, and retail along Route 41. Annual maintenance programs available.
Highland Park sits at the intersection of architectural history and affluent North Shore living. The city has a remarkable range of housing styles — Prairie-style homes and Arts and Crafts bungalows in the older in-town neighborhoods, Tudor Revival and Colonial estates in Ravinia and Sherwood Forest, lakefront properties with sweeping views and exposure to northeast winds, and newer custom builds in Briergate and Sunset Woods that bring their own complexity.
That architectural diversity is what makes Highland Park roofing work interesting — and what makes it unsuitable for contractors who treat every roof as interchangeable. A cedar shake replacement on a Ravinia Tudor calls for different materials, different detailing, and different conversations about aesthetics than a TPO reroof on a commercial building along Park Avenue. Both are work we handle, but we treat them as distinct disciplines.
Leaders Roofing Corp has been working in Highland Park and across Lake County since 1996. We're a family-owned company based in Mount Prospect, holding Illinois Roofing Unlimited License #104.010248. We handle residential and commercial work — full replacements, repairs, storm damage response, and ongoing commercial maintenance programs. Our crew is local. We're here year-round, not just when storms bring in out-of-state contractors looking for quick work.
Highland Park's housing stock rewards contractors who pay attention. The older properties in Ravinia and the historic in-town neighborhoods have steep pitches, multiple dormers, intricate valley work, and chimneys that require careful flashing — not roofing cement slathered over a problem. Lakefront estates add the complication of wind exposure and, in some cases, distinctive architectural materials like slate and copper that need to be matched or properly transitioned when sections are replaced.
Newer custom builds in Briergate and Sunset Woods typically have more straightforward geometry, but they're also larger — 3,000 to 5,000 square feet of roof area is common — and their owners have expectations about material quality and site management that need to be met. Protecting established landscaping, keeping the job site orderly, and communicating clearly through the project aren't optional extras on a North Shore project; they're baseline requirements.
Highland Park replacement pricing tiers by material. Designer architectural shingles with copper flashing: $40,000 to $90,000. Cedar shake with full copper scope: $70,000 to $140,000+. Synthetic slate: $80,000 to $150,000. Natural slate with comprehensive copper work on Sherwood Forest or Ravinia estates: $130,000 to $300,000+. Lakefront estates and homes with steep multi-plane rooflines push toward the upper end of whatever material tier is specified. We don't pad estimates or quote artificially low to win the bid — you'll get a complete written line-item breakdown before deciding.
We work with material systems from CertainTeed, GAF, and Owens Corning for shingle work. For homes transitioning from cedar shake, we can discuss Class IV impact-resistant architectural shingles that replicate the dimensional profile — more on that below. For projects involving slate or other specialty materials, we source through vetted suppliers and bring appropriate installation expertise.
Cedar shake has been the premium roofing material of choice on North Shore homes for generations, and many Highland Park properties — especially those built between 1920 and 1980 — either have original cedar or have been re-roofed with it at some point. The problem is that aging cedar on most of these homes is now well past its useful life, and the question of what to replace it with deserves a more nuanced conversation than the roofing industry often provides.
Some contractors in this market push expensive synthetic shake products — Brava, DaVinci, and similar composite tiles — as the only appropriate aesthetic replacement for cedar. These are good products, but they carry a significant price premium over architectural shingles, and the visual difference at normal viewing distance is much smaller than the cost difference suggests.
Our recommendation for most Highland Park cedar shake replacements is a Class IV impact-resistant architectural shingle in a dimensional profile that replicates the hand-split shake aesthetic:
A heavy laminated architectural shingle with a deeply dimensional profile that reads as period-appropriate on older Highland Park homes. Class IV impact rating (UL 2218). Available in natural cedar tones. One of the most aesthetically convincing shake alternatives in the shingle category.
GAF's premium designer shingle in the slate/shake aesthetic category. Dimensional profile, Class IV impact resistance, Lifetime warranty. Often the right choice for homes in Ravinia and similar neighborhoods where the visual character of the original material matters.
Many homeowner's insurance carriers offer premium discounts for Class IV impact-resistant roofing — sometimes 20–30% reduction on the wind/hail portion of the premium. Over the roof's life, those savings can offset the modest upcharge over standard architectural shingles.
If you want real cedar, we install it. Blue Label or No. 1 grade cedar shake, properly installed with correct exposure and ventilation, is a legitimate choice. We just want you to understand the maintenance requirements and cost difference before you commit.
Highland Park's lakefront position creates a specific weather exposure profile. Northeast winds off Lake Michigan deliver lake-effect precipitation events, and the city is in the path of storm systems that move through the Chicago region. The August 2025 hail events that hit northern Lake County affected Highland Park neighborhoods along with communities to the west and north — storm chasers were working the area heavily in the weeks following.
Highland Park homeowners dealing with potential hail damage should take a few steps before committing to any contractor:
We've worked with Highland Park homeowners through the insurance claims process for decades. We're honest about damage severity — if a claim isn't warranted by the actual damage, we'll tell you, even if that means you don't replace the roof right now.
Portions of Highland Park carry historic designation or are subject to review for projects visible from the public way. The Park Avenue Historic District and similar designations mean that roofing material choices may require approval before installation through the City of Highland Park's building and historic preservation review process. HOA covenants in some Highland Park neighborhoods also specify approved material types and colors.
We handle these processes as part of the project. Before ordering materials on any job with historic or HOA constraints, we confirm the material selection is approvable, obtain any required municipal permits, and document the approval in writing. This protects you from having to redo work that didn't meet guidelines — a situation that's expensive and avoidable with proper process upfront.
Our experience on North Shore properties means we understand what architectural sensitivity looks like in practice: matching ridge profile height to the original material, selecting colors that read as period-appropriate rather than incongruous, and keeping sight lines and curb appeal in mind when making recommendations. A re-roofed historic property should look right. We take that seriously.
Highland Park's commercial real estate includes the downtown Park Avenue corridor with its mixed-use buildings, the professional office district, and scattered retail and light industrial along Route 41. Property managers and building owners in these areas have flat and low-slope roofing systems that require a different skill set than residential pitched work.
Leaders handles commercial flat roofing in Highland Park through our Unlimited License — TPO, modified bitumen, and EPDM systems for retail, office, and mixed-use buildings. We also offer annual commercial roof maintenance programs: inspection, seam and flashing re-sealing, drain clearing, and written condition reports that building owners can use for capital planning and insurance documentation. A maintained commercial flat roof significantly outlasts one that gets attention only when it leaks.
For historic homes in Highland Park — particularly in the Ravinia district and older in-town neighborhoods — architectural shingles with a dimensional profile best replicate the look of period materials without the maintenance demands of cedar shake. CertainTeed Grand Manor and GAF Camelot II are both Class IV impact-resistant options with a hand-split shake appearance that reads as appropriate on older homes. For properties in formally designated historic districts, we work with the municipality on material approvals before ordering anything.
Highland Park pricing tiers with material specification. Designer architectural shingles on a typical home: $40,000 to $90,000. Cedar shake (hand-split or tapersawn Western Red Cedar with copper flashing): $70,000 to $140,000+. Synthetic slate (DaVinci, Brava, EcoStar): $80,000 to $150,000. Natural slate with full copper flashing scope: $130,000 to $300,000+, with the high end reserved for Sherwood Forest and Ravinia estates with comprehensive copper accent work. Larger lakefront estates and homes with complex multi-plane rooflines push toward the upper end of each tier. We provide line-item written estimates so material grades, copper weight, and project scope are transparent before any commitment.
Cedar shake can still make sense for the right property and homeowner, but it requires more maintenance than most people expect — annual inspection, periodic treatment, and more frequent replacement at 20 to 25 years compared to a Class IV architectural shingle's comparable performance. Cedar is also significantly more expensive to install and is no longer eligible for some insurance discounts. For most Highland Park homeowners replacing aging cedar shake, a Class IV architectural shingle like CertainTeed Grand Manor or GAF Camelot II delivers a comparable visual profile at a lower installation cost, lower maintenance burden, and often qualifies for an insurance premium reduction. We'll install cedar if that's your preference — we just want you to have the full picture.
Yes. We have experience working in architecturally sensitive neighborhoods on the North Shore, including areas with HOA guidelines and municipal historic district requirements. We work through material approvals before ordering, obtain required permits with the City of Highland Park, and coordinate with HOA management when required. Our approach on historic properties is to match the visual character of the existing architecture — material profile, color, and scale all matter.
Highland Park's lakefront position means more frequent freeze-thaw cycling and greater ice dam risk than inland suburbs. Lake-effect precipitation events can drop heavy, wet snow that taxes older roofing systems. Ice dams form when attic heat melts snow at the ridge and that water refreezes at the cold eave — the result is water backing up under shingles and into the attic or wall cavity. Homes with inadequate attic insulation or poor soffit-to-ridge ventilation are most vulnerable. When we work on a Highland Park roof, we assess the ventilation situation as part of the project — catching that problem at replacement time prevents ice dam callbacks.
We serve all of Highland Park and surrounding Lake County communities. Call (847) 312-2727 for a free estimate.
We work across Lake County and the North Shore. If you're a homeowner in one of these neighboring communities, our service area pages cover specifics for each:
Free estimates on residential and commercial roofing. Call (847) 312-2727 or fill out the form.