Roof Replacement · Winnetka, IL
Roof Replacement in
Winnetka, IL
When a slate, tile, or copper roof has reached the end of its life, a full-system replacement protects an architecturally significant home for generations. Complete tear-off and a deck-up rebuild by an Arlington Heights owner who’s on every job. Serving Winnetka since 2007.
- Local to the NW suburbs — based minutes away in Arlington Heights
- 5.0★ Google rating from verified customers
- Manufacturer material warranty + our own workmanship warranty
- Licensed, bonded & insured in Illinois
What's Included
What a Complete Roof Replacement Includes
A real replacement isn’t new shingles laid over old problems. We strip the roof down to the deck, inspect and repair the structure underneath, and rebuild the whole system — so you’re not paying to bury rot, bad ventilation, or failed flashing for the next crew to find.
Full tear-off and haul-away of the existing roof
Deck inspection & replacement of rotted or damaged sheathing
Ice-and-water shield at eaves, valleys & every penetration
Synthetic underlayment across the entire roof
New flashing, drip edge & in-house-fabricated metal details
Properly sized intake/exhaust ventilation (ridge vent)
Your chosen roofing material, installed to manufacturer spec
Full cleanup with magnetic nail sweep & debris haul-away
Materials
Roofing Materials We Install
From architectural asphalt to premium metal, slate, and cedar, we install and fabricate the full range — and we’ll help you weigh cost, lifespan, and the look that fits your home and block.
- Architectural & dimensional asphalt
- Standing-seam & custom metal
- Natural & synthetic slate
- Cedar shake
- Clay tile
- Flat / low-slope membrane (TPO, PVC, mod-bit)
- Copper & architectural metal accents
Local Context
Why Winnetka Roofs Reach Replacement
Winnetka’s housing stock leans toward older, architecturally significant homes — Tudors, Colonials, and lakefront estates with steep slate, tile, and cedar roofs and elaborate copper detailing. These systems are built to last, but decades of North Shore weather off Lake Michigan eventually take them past repair: slate delaminates, cedar weathers through, and copper and flashing fail across the roof. At that point a full replacement in matching materials is the honest call. Replacing these isn’t a shingle swap — it’s matching specialty materials and fabricating metalwork to the original profile, which is our specialty.
- Architect-designed Tudors and Colonials on aging slate, tile, and cedar
- Lakefront estates with steep, ornate rooflines reaching system end-of-life
- North Shore exposure: ice dams, freeze-thaw, wind-driven rain, and hail
Not an emergency leak? See roof repair in Winnetka instead.
Repair or Replace?
Signs It's Time to Replace, Not Repair
You’re paying to repair the same roof again and again
Multiple active leaks, or sagging/soft spots in the roof deck
Storm or hail damage your insurer has declared a total loss
You’re selling and the roof is a flagged item on inspection
Why Black Square
Why Winnetka Homeowners Choose Black Square Roofing
We Fabricate Our Own Metal Details
No Upsells — Honest Repair-vs-Replace
Manufacturer + Workmanship Warranty
Owner on Every Job
Mark is on-site overseeing the tear-off and install — not managing from an office.
The Process
How a Roof Replacement Works
1
In-Home Consultation & Estimate
We inspect the roof and attic, talk through your goals and timeline, and give you a detailed written estimate. No pressure, no hidden costs.
2
Material Selection
We help you choose the right material, color, and warranty tier for your home and budget — and order it in.
3
Tear-Off & Deck Inspection
We strip the old roof, inspect the deck, and repair any rot or damage before anything new goes down.
4
System Installation
Underlayment, ice-and-water shield, flashing, ventilation, and your new roofing material, installed to manufacturer spec.
5
Final Walkthrough & Warranty
Owner-led final check, magnetic nail sweep, full cleanup, and your warranty documentation in hand.
Service Area
Serving Winnetka & the Surrounding Suburbs
Based in Arlington Heights, we install new roofs across Winnetka and the neighboring North Shore villages. Not sure if we reach you? Call — we likely do.
Winnetka
Kenilworth
Glencoe
Northfield
Wilmette
Glenview
Northbrook
Highland Park
FAQ
Common Questions
Do you replace slate, tile, and copper roofs in Winnetka?
Yes — full-system replacement of premium materials is where our in-house fabrication matters most. We replace slate, tile, cedar, and copper and cut flashing and metal details to fit the roofline, not force off-the-shelf parts.
How long does a roof replacement take in Winnetka?
A standard asphalt roof is often a 1–3 day job, but slate, tile, copper, and ornate estate rooflines take longer to do right. We give you a realistic timeline with your estimate.
Will you tear off the old roof or install over it?
We tear off. On these homes especially, laying new over old buries deck and structural problems and never lasts. We strip to the deck, inspect the structure, and rebuild the system.
Will a new roof match the look of my home?
Yes. We match the original material and profile — slate, tile, cedar, or copper — and fabricate the metal details in-house so the new roof reads as right for the architecture, not generic.
What warranty comes with a new roof?
Your new roof carries the material manufacturer’s warranty plus our own workmanship warranty on the install. We spell out both in writing before we start.
Plan Your Winnetka Roof Replacement
No pressure — just an honest assessment of whether it’s time, what your options are, and what it takes to do it right, from an owner who’s been doing this since 2007.