On Time Roofing

Roofing, Siding, and Window Overhaul: Which Comes First?

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When planning a full exterior renovation, homeowners often ask: Which should come first—roofing, siding, or windows? At On Time Roofing, we’ve helped hundreds of homeowners throughout Westchester County, NY tackle this exact project. While all three components—roof, siding, and windows—play a critical role in protecting and beautifying your home, there is a strategic order that ensures long-term durability, energy efficiency, and cost savings. In this blog, we’ll break down the best sequence to follow, why it matters, and how working with a trusted roof contractor in Westchester County can make all the difference.

Step One: Roofing Comes First

Your roof is your home’s first line of defense. If your roofing system is failing, water can easily seep down behind new siding or into window frames, causing damage that may go unnoticed until it’s costly to fix. By replacing or repairing your roof first, you:
  • Prevent water intrusion during the rest of your renovation 
  • Provide a stable foundation for siding and trim alignment 
  • Ensure flashing and underlayment are installed properly 
Hiring a licensed and experienced roofing contractor like On Time Roofing ensures your home is protected from above before other components are added. We use premium roofing materials like Owens Corning and CertainTeed for long-lasting performance and weather resistance.

Step Two: Windows Are Next

Once your new roof is in place, the next logical step is replacing your windows. Why?
  • New windows are more energy-efficient and reduce drafts 
  • Window trim and casing can be better integrated with the new siding 
  • Proper sealing around windows is easier before siding installation 
This is especially true if your existing window frames are leaking or deteriorating. Our team can coordinate your window upgrade to fit seamlessly into your full exterior plan. Replacing windows before siding helps avoid cutting and patching into brand-new siding later.

Step Three: Finish with Siding

Your home’s siding is the final piece of the puzzle. It not only enhances curb appeal but also serves as a protective shell against the elements. Once your roof and windows are secure and up-to-date, siding installation ties the whole renovation together. On Time Roofing provides siding services in Westchester County, NY that are custom-fitted to your home’s new exterior features. Whether you’re choosing vinyl, fiber cement, or another durable material, siding is the finishing touch that ensures everything looks cohesive and functions at its best.

Why Order Matters

Doing these projects in the wrong order can lead to:
  • Water damage behind siding or windows 
  • Increased labor costs due to rework 
  • Misaligned flashing or trims 
  • Poor energy efficiency 
A full-service company like On Time Roofing understands the bigger picture. We create renovation timelines that save you time and money while protecting your home throughout every stage.

Work With Westchester’s Trusted Roofing and Siding Experts

At On Time Roofing, we’ve been proudly serving Westchester County homeowners since 2008. From roof repair services to full siding and window upgrades, we manage every phase of your project with care, skill, and attention to detail.

Why choose us?

  • Licensed and insured roofing professionals 
  • High-quality, brand-name roofing materials 
  • Competitive pricing and honest quotes 
  • Fast turnaround times 
  • Proven 5-star reputation in Westchester County, NY 

Ready to Plan Your Exterior Overhaul?

If you're planning a major renovation, timing and strategy are everything. Let On Time Roofing help you make the right call—starting with a solid roof, energy-efficient windows, and finally a stunning siding upgrade. Call us today at 914-924-4869 to schedule your free estimate and find out why we’re a leading roofing contractor in Westchester County, NY.
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