FOR RESIDENTIAL & COMMERCIAL
Roofing & Exterior Services in Winnetka, IL
Winnetka’s homes demand a level of roofing craftsmanship that most contractors can’t deliver. Lakeland Exteriors & Roofing has been working on Winnetka properties for over 30 years — cedar shake replacements, historic slate work, premium shingle systems, and custom gutter installations on some of the most demanding residential projects on the North Shore.
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CertainTeed Certified Master Shingle Applicator
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Licensed in Illinois (#104.018650)
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5.0 across 240+ reviews
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30+ Years Serving the North Shore
Serving Winnetka Homeowners
Winnetka is the most demanding roofing market in Lakeland’s service area, and that’s not a complaint and it’s why the work matters here. The village has some of the oldest, largest, and most architecturally intricate residential properties in Illinois: Georgian estates, Tudor Revival mansions, Prairie-style homes, and lakefront properties with roof geometries that require a contractor who understands what they’re working with before a single shingle comes off.
Cedar shake roofs are still common in Winnetka’s established neighborhoods, and many were installed 30 to 40 years ago. Replacing a cedar shake roof on a large Winnetka estate is a multi-day project that demands careful decking assessment, meticulous flashing work, and a finished installation that meets the visual standards of the surrounding property. These are not jobs where cutting corners goes unnoticed.
The lakefront location compounds the technical challenge. Winnetka sits directly on Lake Michigan and sees the most intense weather exposure of any community in the service area: direct northeast winds off the lake, salt air accelerating metal corrosion, and lake-effect precipitation that tests every flashing seam and valley detail. Roofing systems in Winnetka simply age faster than they do a few miles inland, which is why quality of installation matters more here than almost anywhere else.
Lakeland’s Skokie office is close enough to Winnetka that response times are fast and crew familiarity with North Shore construction standards is built in.
OUR SERVICES
Roofing & Exterior Services We Provide in Winnetka
From shingle replacements to full tear-offs, we protect Chicagoland homes with CertainTeed’s Complete Roofing System and 35+ years of crew experience. Honest estimates, clean job sites, and a 50-year material warranty backed by a 10-year Lakeland workmanship warranty.
Property managers, building owners, and facility teams trust Lakeland for TPO, EPDM, PVC, and built-up roofing systems that minimize tenant disruption. Our commercial foremen each bring 35+ years of experience to every project.
Architectural and designer shingle roofing systems installed for long-term protection, curb appeal, and dependable performance in Midwest weather.
Protect and refresh your home’s exterior with professional siding installation and replacement. We work with durable materials built to stand up to Midwest weather, with the same clean finish and honest pricing as our roofing work.
TPO, EPDM, PVC, and other low-slope roofing systems installed for dependable waterproofing, energy performance, and long-term protection.
Properly installed gutters protect your foundation, fascia, and landscaping. We install 6″ K-style .032-gauge aluminum seamless gutters with hidden hangers and box miters — built to last and cut to fit your home exactly.
Hit by a storm? We move fast. Free damage assessments, insurance claim support, and emergency tarping when you need it — for both homes and commercial properties across Illinois and Wisconsin.
Standing seam and specialty metal roofing solutions built for durability, energy efficiency, and a clean finished look on residential and commercial properties.
Residential Roofing
Commercial Roofing
Storm & Hail Damage
Hit by a storm? We move fast. Free damage assessments, insurance claim support, and emergency tarping when you need it — for both homes and commercial properties across Illinois and Wisconsin.
Metal Roofing
Standing seam and specialty metal roofing solutions built for durability, energy efficiency, and a clean finished look on residential and commercial properties.
Flat Roofing
TPO, EPDM, PVC, and other low-slope roofing systems installed for dependable waterproofing, energy performance, and long-term protection.
Gutters & Downspouts
Properly installed gutters protect your foundation, fascia, and landscaping. We install 6″ K-style .032-gauge aluminum seamless gutters with hidden hangers and box miters — built to last and cut to fit your home exactly.
Shingle Roofing
Architectural and designer shingle roofing systems installed for long-term protection, curb appeal, and dependable performance in Midwest weather.
Exterior Siding
Protect and refresh your home’s exterior with professional siding installation and replacement. We work with durable materials built to stand up to Midwest weather, with the same clean finish and honest pricing as our roofing work.
Why Winnetka Property Owners Choose Lakeland
License #104.018650. Full general liability and workers’ compensation on every job.
Thirty years of North Shore experience
Lakeland has been working on properties like Winnetka’s for decades. The crew understands the construction methods, the materials, and the standards that Winnetka homeowners expect — and they work accordingly.
CertainTeed certified for the full warranty
The CertainTeed Certified Master Shingle Applicator designation is what makes the 50-year material warranty available. Not every contractor in the area holds it. Lakeland does, and every qualifying Winnetka installation is covered.
Clean, respectful job sites
Winnetka properties are maintained to a high standard. Lakeland’s crews clean up completely at the end of each work day and treat the property with the same care they’d give their own. That’s not a sales line — it’s what our reviews say consistently.
Trusted by 1000+ Property Owners Across Illinois & Wisconsin
5.0 across 240+ reviews
