FOR RESIDENTIAL & COMMERCIAL

Roofing & Exterior Services in Wilmette, IL

Lakeland Exteriors & Roofing has been serving Wilmette homeowners for over 30 years. From the lakefront estates along Sheridan Road to the tree-lined streets further west, we handle residential roof replacements, storm damage repairs, gutters, siding, and commercial flat roofing across all of Wilmette.

  • CertainTeed Certified Master Shingle Applicator
  • Licensed in Illinois (#104.018650)
  • 5.0 across 240+ reviews
  • 30+ Years Serving the North Shore

Serving Wilmette Homeowners & Businesses

Wilmette is one of the most architecturally varied communities on the North Shore. The housing stock ranges from late-Victorian and Tudor Revival homes in the historic lakefront neighborhoods to craftsman bungalows, mid-century ranches, and newer construction further west of Green Bay Road. That range means roofing work in Wilmette requires genuine experience with different construction eras and not just the ability to put down shingles, but the knowledge to assess what’s underneath them on a 100-year-old house and make decisions that will hold for another 30 years.

Cedar shake roofs remain common in Wilmette’s older neighborhoods, and many are at or past the end of their serviceable life. A deteriorating cedar shake roof is one of the most involved replacement projects a contractor can take on: the decking often requires partial or full replacement, the underlayment needs to be brought to current standards, and flashing details need careful attention in a home that age. Lakeland has replaced hundreds of cedar shake roofs across the North Shore, including many in Wilmette.

Wilmette’s location on Lake Michigan means it sees the same accelerated weather exposure that affects the rest of the North Shore: lake-effect storms, high wind events, and the hard freeze-thaw cycles that push water into flashing seams and accelerate shingle wear faster than inland communities experience.

Lakeland’s Skokie office at 5250 Old Orchard Rd is a short drive south of Wilmette, making same-day response standard for most estimates and storm assessments.

OUR SERVICES

Roofing & Exterior Services We Provide in Wilmette

Residential Roofing

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.

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WE DO
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.
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Residential Roofing

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.
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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 Wilmette Property Owners Choose Lakeland

License #104.018650. Full general liability and workers’ compensation on every job.

Experience with older homes

Wilmette’s housing stock includes homes from the 1880s through the 1960s. Lakeland’s crews have the experience to work on older construction correctly understanding original framing, identifying hidden damage, and installing new systems to current standards without compromising the character of the home.

CertainTeed certified

As a CertainTeed Certified Master Shingle Applicator, Lakeland can issue the full CertainTeed warranty up to 50 years on materials and 10 years on workmanship on every qualifying installation in Wilmette. That warranty requires certification to issue. Many contractors can’t offer it.

North Shore track record

Thirty-plus years of work on the North Shore means Lakeland understands what this market expects: clean job sites, clear communication, and installations that hold up to Lake Michigan weather. Every Wilmette job gets the same standard.

Trusted by 1000+ Property Owners Across Illinois & Wisconsin

The Quality of the Workmanship was Excellent! They cleaned the gutters and installed Raindrop Gutter Guard. All questions were answered promptly. Job site was cleaned up like they were never here.
Professional, Courteous, and Worked Hard! Looked at the areas we tagged in a timely manner. Lakeland came highly recommended to me after I had a poor experience with another roofing company.
Superior Services for our Roofing needs! We had a roof at the end of its life. Lakeland team inspected the roof and gave us an honest opinion of its lifespan. Would highly recommend to anyone looking for a new roof!
Great job at the Exact Quoted Price. Referred by two relatives that had good experiences. Lakeland's workmanship appears well done and mine has a ten year warranty. Very pleased.
Lakeland exceeded my expectations! I couldn't be happier with our new roof and the experience working with Lakeland. Easy Process, high quality of work and professionalism was impressive.
My Experience with Lakeland was great! The crew was friendly and responsive to my requests. They cleaned up at end of the day. The quality of the product and the workmanship were great.
Good old Fashioned Service and Reliability! Highly skilled professionals. Not only did they repair all of our storm damage, but they took the time to educate us and do the job completely right.
Lakeland Team Delivered an Outstanding Product! Lakeland delivered hands down, the experience has exceeded my expectations 10 fold!! I cannot say enough about the clean up and thoughtful workmanship.
Great from start to finish. Very professional. The estimate was given quickly, professionally and accurately. Work was completed very quickly and the workmanship was excellent. Area was cleaned completely before they left. A very nice surprise to find such good workmanship in a timely manor, in these days of long waits and poor workmanship. Fair priced. I would recommend them highly.
Total roof replacement and gutter guards. From beginning to end, excellent communication, workmanship top tier, and cleanup was well done at the end of each day. They take pride in their work, and would not take payment (it was offered), until even the smallest detail was completed to our and their satisfaction. Derek was wonderful, he gave us advice at each step with no pressure (including info to share with our HOA). This was very welcomed, and resulted in informed decisions. The roof looks great!
Lakeland did a great job. They were on time, fast and professional. Overall great experience.
I would definitely use Lakeland exteriors for any exterior work I would need done. They do quality work and they have very professional employees. I would definitely refer them to anyone needing any exterior repairs or replacement projects.