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The Trusted Roofing Contractor for Winnetka’s Finest Homes

Wolf Development provides Winnetka homeowners with unparalleled craftsmanship in slate, cedar, synthetic, clay, and metal roofing systems.

Our Appreciation for Winnetka

A Community of Distinction and Architectural Beauty

Since 2016

Our Appreciation for Winnetka Roofing Specialists

Our Appreciation for Winnetka

A Community of Distinction and Architectural Beauty

Winnetka is one of the North Shore’s most celebrated communities, known for its tree-lined streets, lakefront parks, and architectural heritage. From the sandy stretches of Elder Lane and Lloyd Beach to the tranquil beauty of the Skokie Lagoons, Winnetka offers a lifestyle that is both serene and sophisticated. Downtown Winnetka along Green Bay Road adds charm with its boutique shops and historic character, while neighborhoods showcase homes designed by legendary architects like George W. Maher and Robert Seyfarth.

The village’s commitment to preserving historic architecture is unmatched. Tudor, Colonial, and Prairie-style estates sit side by side with modern custom homes, each telling its own story. For homeowners here, a roof is more than protection — it’s a defining feature of the property’s curb appeal and legacy.

At Wolf Development, we share Winnetka’s respect for history and craftsmanship. Whether restoring a Vermont slate roof on a lakefront estate or installing a DaVinci synthetic shake system on a newer home, we ensure every project enhances the architectural character of this remarkable community.

Your Local Winnetka Roofing Specialists

Roofing Built for Winnetka’s Homes and Standards

Wolf Development is proud to serve homeowners throughout Winnetka. We understand the North Shore climate, building codes, and preservation standards, and we tailor our roofing solutions accordingly.

Our roofs aren’t just weather barriers — they’re architectural features designed to enhance property value while protecting your home for decades.

Why choose us?

Mastery in Every Roofing Material

Whether you’re restoring a historic slate roof on Sheridan Road or adding a modern metal roof to a new build, our craftsmen are certified experts across all premium materials
Timeless elegance and unmatched longevity.
Rustic warmth with natural insulation.
Slate & shake looks, modern performance.
Architectural shingles with slate-like appeal.
Energy-efficient, modern, and long-lasting.
Mediterranean beauty, natural fire resistance.
Lightweight durability with classic charm.
Wood shake appearance, no rot or warping.
The gold standard for low-slope protection.
Eco-friendly composites with authentic detail
Classic layered look, durable protection.
roofing contractor David Wilk talking to worked on a roofing project
The Wolf Difference

Why Winnetka Homeowners Choose Wolf Development

roofing contractor David Wilk talking to worked on a roofing project
When it comes to protecting and enhancing your home, you deserve more than a standard roofer. Winnetka homeowners trust us because:
Local Architectural Fluency
We respect Winnetka’s design standards and preservation guidelines.
Owner-Led Projects
Every project is personally overseen by David, ensuring accountability and quality.
Portfolio of Local Work
We’ve enhanced homes throughout the North Shore and proudly share our results.
Unwavering Respect for Your Property
Daily cleanup, meticulous protection of landscaping, and a professional crew at all times.

Natural Slate Roof & Copper Restoration for a Lakefront Kenilworth Estate

Featured Winnetka Project: Natural Slate Restoration

This Georgian home on Sheridan Road underwent a full Vermont Black Slate roof replacement. The result honors the home’s historic architecture while providing a new century of durability.

Client

Peterson Family

Location

Kenilworth, IL

Duration

10 Weeks

Date

March 2023

Your Roofing Questions, Answered

Everything you need to know about working with Wolf Development.

How long does a slate roof installation take?

Most slate projects take 2–4 weeks depending on the home’s size and complexity. This Lake Forest project was completed in 3 weeks.

How much does a slate roof cost compared to other materials?

Slate is a premium investment. While the upfront cost is higher than asphalt shingles or synthetics, its 100+ year lifespan often makes it the most cost-effective choice over time.

Do you handle historic homes differently than newer homes?

Yes. We take extra care to preserve architectural details and comply with historic preservation guidelines common in towns like Lake Forest, Winnetka, and Hinsdale.

What maintenance does a slate roof require?

Minimal. Occasional inspections and replacing the rare broken tile are typically all that’s needed. Slate requires far less upkeep than cedar or asphalt.

What areas do you serve for slate roof projects?

We work throughout Chicagoland, with many of our slate and cedar projects in Lake Forest, Winnetka, Glencoe, Hinsdale, and surrounding suburbs.

Still have questions?

Reach out directly. We’re here to talk.

Protect and Enhance Your Home’s Legacy

Ready to discuss your project? Schedule a complimentary, no-obligation consultation with David to explore the best roofing solution for your home.
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